Name: 124-83-4|(1R,3S)-1,2,2-Trimethylcyclopentane-1,3-dicarboxylic acid|98%
Brand: Ambeed
SKU: A555427
Price: 8.0 USD
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1
[ 124-76-5 ]
[ 124-83-4 ]
(1R)-cis-camphoric acid di-((1R)-isobornyl ester) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 3944

2
[ 464-49-3 ]
[ 124-83-4 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 1963 - 1966
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1771 - 1779
[3]Synthetic Communications,2001,vol. 31,p. 3031 - 3036
[4]Patent: DE765525,1940,
DRP/DRBP Org.Chem.,
[5]Bulletin de la Societe Chimique de France,1949,p. 894,897
[6]Journal of the Chemical Society. Perkin transactions I,1983,p. 1465 - 1474
[7]Journal of Organometallic Chemistry,2014,vol. 768,p. 36 - 41
[8]Patent: US2333718,1940,

3
[ 124-83-4 ]
[ 595-32-4 ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 1707 - 1715
[2]Chemische Berichte,1894,vol. 27,p. 2010
Acta Soc. Sc. Fenn.,vol. 21,p. 154,189
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 7101 - 7105
Angew. Chem.,2018,vol. 130,p. 7219 - 7223,5
[4]Journal of the American Chemical Society,2018,vol. 140,p. 13566 - 13569

4
[ 124-83-4 ]
[ 116481-14-2 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 10505 - 10513
[2]Synthetic Communications,2001,vol. 31,p. 3031 - 3036
[3]Tetrahedron Asymmetry,2015,vol. 26,p. 1256 - 1260
[4]Tetrahedron Asymmetry,1992,vol. 3,p. 5 - 8
[5]Inorganica Chimica Acta,2018,vol. 481,p. 171 - 175
[6]Dalton Transactions,2016,vol. 45,p. 15303 - 15316
[7]European Journal of Inorganic Chemistry,2006,p. 839 - 849
[8]Roczniki Chemii,1937,vol. 17,p. 105,106
Chemisches Zentralblatt,1937,vol. 108,p. 49
[9]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1771 - 1779
[10]Journal of Organometallic Chemistry,2014,vol. 768,p. 36 - 41
[11]Applied Organometallic Chemistry,2015,vol. 29,p. 425 - 432
[12]Journal of Coordination Chemistry,2016,vol. 69,p. 1463 - 1472
[13]Tetrahedron Asymmetry,2017,vol. 28,p. 381 - 386
[14]Synthesis,2017,vol. 49,p. 2852 - 2864
[15]Polyhedron,2017,vol. 137,p. 147 - 156
[16]Applied Organometallic Chemistry,2020,vol. 34

5
[ 124-83-4 ]
[ 46241-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In hexane; for 24h;Reflux;	Example 170; methyl ( 1 R.3 SV 3 -( ( IY5ZV4-butyl-2-tert-butylisothiazol-5 (2HV ylidenei amino I carbonvO- 1,2,2-trimethylcvclopentanecarboxylate; A mixture of (+)-camphoric acid (Aldrich, 2.00 g, 10.0 mmol) and phosphorus pentachloride (Aldrich, 4.16 g, 20.0 mmol) in hexane (75 mL) was heated to reflux and stirred for 24 hours. After cooling to ambient temperature, the reaction mixture was concentrated by rotary evaporator to give a pale yellow oil. The crude bis acid chloride (474 mg, 2.00 mmol) was added to a mixture of the product from Example 92B (425 mg, 2.00 mmol) and triethylamine (1.01 g, 10.0 mmol) in anhydrous tetrahydrofuran (12 mL). The mixture was stirred for 2 hours. Anhydrous methanol (10 mL) was added and the resulting mixture was stirred overnight. The mixture was concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel, 5-25% ethylacetate in hexanes) afforded 343 mg (42%) of the title compound. 1H NMR (DMSO-J6) delta 0.53 (s, 3H), 0.90 (t, J = 7.3 Hz, 3H), 1.20 (s, 3H), 1.23 (s, 3H), 1.23-1.40 (m, 2H), 1.41-1.50 (m, IH), 1.57 (s, 9H), 1.57-1.67 (m, 2H), 1.71-1.84 (m, IH), 2.24-2.36 (m, IH), 2.41-2.48 (m, IH), 2.61-2.67 (m, 2H), 3.00- 3.06 (m, IH), 3.59 (s, 3H), 8.52 (s, IH). MS (ESI+) m/z 409 (M+H)+. Anal, calcd. for C22H36N2O3S: C, 64.67; H, 8.88; N, 6.86. Found: C, 64.52; H, 8.76; N, 6.84.; Example 175; ethvUlS.3RV3-((r(5ZV4-butyl-2-tert-butylisothiazol-5(2HVylidene]aminolcarbonylV2.2.3- trimethylcyclopentanecarboxylate; A mixture of (+)-camphoric acid (Aldrich, 2.00 g, 10.0 mmol) and phosphorus pentachloride (Aldrich, 4.16 g, 20.0 mmol) in hexane (75 mL) was heated to reflux and stirred for 24 hours. After cooling to ambient temperature, the reaction mixture was concentrated by rotary evaporator to give a pale yellow oil. The crude bis acid chloride (356 mg, 1.50 mmol) was added to a mixture of the product from Example 92B (319 mg, 1.50 mmol) and triethylamine (455 g, 4.50 mmol) in anhydrous tetrahydrofuran (12 mL). The mixture was stirred for 2 hours. Anhydrous ethanol (20 mL) was added and the resulting mixture was stirred overnight. The mixture was concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel, 5-25% ethyl acetate in hexanes) afforded 327 mg (52%) of the title compound. 1H NMR (DMSO-J6) delta 0.51 (s, 3H), 0.90 (7.3 Hz, 3H),1.18 (t, J = 7.0 Hz, 3H), 1.21 (s, 3H), 1.23-1.36 (m, 2H), 1.31 (s, 3H), 1.40-1.50 (m, IH), 1.57 (s, 9H), 1.57-1.67 (m, 2H), 1.71-1.85 (m, IH), 1.98-2.10 (m, IH), 2.62-2.67 (m, 2H), 2.70- 2.81 (m, IH), 2.82-2.89 (m, IH), 3.98-4.16 (m, 2H), 8.51 (s, IH). ). MS (ESI+) m/z 423 (M+H)+. Anal, calcd. for C22H36N2O3S: C, 65.36; H, 9.06; N, 6.63. Found: C, 65.02; H, 8.97; N, 6.49.; Example 177; methvUlS.3R)-3-((r(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]aminolcarbonv?- 2,2,3-trimethylcyclopentanecarboxylate; A mixture of (+)-camphoric acid (Aldrich, 2.00 g, 10.0 mmol) and phosphorus pentachloride (Aldrich, 4.16 g, 20.0 mmol) in hexane (75 mL) was heated to reflux and stirred for 24 hours. After cooling to ambient temperature, the reaction mixture was concentrated by rotary evaporator to give a pale yellow oil. The crude bis acid chloride (474 mg, 2.00 mmol) was added to a mixture of the product from Example 92B (425 mg, 2.00 mmol) and triethylamine (1.01 g, 10.0 mmol) in anhydrous tetrahydrofuran (12 mL). The mixture was stirred for 2 hours. Anhydrous methanol (10 mL) was added and the resulting mixture was stirred overnight. The mixture was concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel, 5-25% ethyl acetate in hexanes) afforded 331 mg (41%) of the title compound. 1H NMR (DMSO-J6) delta 0.50 (s, 3H), 0.90 (t, J = 7.5 Hz, 3H), 1.21 (s, 3H), 1.24-1.36 (m, 2H), 1.30 (s, 3H), 1.42-1.50 (m, IH), 1.57 (s, 9H), 1.57-1.67 (m, 2H), 1.73-1.86 (m, IH), 1.98-2.11 (m, IH), 2.62-2.67 (m, 2H), 2.70-2.81 (m, IH), 2.85- 2.92 (m, IH), 3.60 (s, 3H), 8.51 (s, IH). MS (ESI+) m/z 409 (M+H)+. Anal, calcd. for C22H36N2O3S: C, 64.67; H, 8.88; N, 6.86. Found: C, 64.60; H, 8.63; N, 6.64.

Reference： [1]Tetrahedron Asymmetry,1996,vol. 7,p. 2551 - 2562
[2]Helvetica Chimica Acta,2001,vol. 84,p. 1093 - 1111
[3]Helvetica Chimica Acta,1946,vol. 29,p. 1529,1534
[4]Patent: WO2010/54024,2010,A2 .Location in patent: Page/Page column 145-146; 147-148
[5]Crystal Growth and Design,2010,vol. 10,p. 5291 - 5296
[6]Journal of Materials Chemistry,2012,vol. 22,p. 10352 - 10355

7
[ 124-83-4 ]
[ 68510-42-9 ]

Yield	Reaction Conditions	Operation in experiment
96%		((1R,3S)-1,2,2-Trimethylcyclopentane-1,3-diyl)dimethanol. A solution of <strong>[124-83-4](1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid</strong> (26.25 g, 131 mmol) in THF (400 mL) was cooled in an ice bath (10 C.) and to this was added 1M LiAlH4/THF (328 mL, 328 mmol), dropwise over 1 h. The ice bath was removed and the white slurry was stirred for 5 h at room temperature and 17 h at reflux. After cooling to room temperature, the mixture was diluted with Et2O (500 mL), cooled in an ice bath and carefully quenched with water (12.2 mL), 15% NaOH (12.2 mL) and water (36.7 mL). After stirring for 30 min at room temperature, the white slurry was filtered through a pad of CELITE, then dried (Na2SO4), filtered and concentrated to give ((1R,3S)-1,2,2-trimethylcyclopentane-1,3-diyl)dimethanol (21.665 g, 126 mmol, 96% yield) as a white solid. 1H NMR (500 MHz, CDCl3) delta: 3.73 (1H, dd, J=10.2, 5.3 Hz), 3.58 (1H, d, J=10.7 Hz), 3.51 (1H, dd, J=10.1, 8.5 Hz), 3.46 (1H, d, J=10.7 Hz), 2.04-2.12 (1H, m), 1.89-1.99 (1H, m), 1.55-1.64 (1H, m), 1.31-1.41 (2H, m), 1.22 (2H, brs), 1.02 (3H, s), 1.01 (3H, s), 0.78 (3H, s).
90%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Reflux; Inert atmosphere;	A stirred suspension of LiAlH4 (1.59 g, 42.0 mmol) in THF (100 mL) was cooled to 0 C and a solutionof (1R,3S)-(+)-camphoric acid (2.80 g, 14.0 mmol) in THF (20 mL) was added dropwise. The resulting suspension was warmed to RT and then heated to reflux for 16 h. The resulting solution was cooledto 0 C and diluted with THF (100 mL) and then quenched by sequential dropwise addition of H2O (1.59 mL), aq. NaOH (15 % w/v, 1.59 mL) and H2O (4.77 mL). MgSO4 was added and the resulting suspension was warmed to RT and stirred vigorously for 30 min and then filtered and concentrated in vacuo. Purification by column chromatography (CH2Cl2:MeOH, 95:5) afforded the title compound 2ao as a white solid (2.16 g, 90%). The spectral data matched that previously reported in the literature.35

Reference： [1]Patent: US2009/253677,2009,A1 .Location in patent: Page/Page column 71
[2]Helvetica Chimica Acta,1997,vol. 80,p. 804 - 817
[3]Journal of the American Chemical Society,2018,vol. 140,p. 11916 - 11920
[4]Tetrahedron,2019,vol. 75
[5]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2540 - 2547
[6]Chemische Berichte,1988,vol. 121,p. 363 - 368
[7]Collection of Czechoslovak Chemical Communications,1968,vol. 33,p. 2336 - 2338
[8]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2540 - 2547
[9]Tetrahedron Letters,1980,vol. 21,p. 1963 - 1966
[10]Dalton Transactions,2010,vol. 39,p. 3851 - 3860

8
[ 124-83-4 ]
[ 595-29-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic anhydride; at 0 - 140℃; for 2h;	According to the synthetic route of step A above, camphoric anhydride 2: Weigh (1S,3R)-camphoric acid 1 (20 g, 0.1 mol) and acetic anhydride (12 ml, 0.12 mol) in a round-bottomed flask, reflux at a temperature of 140 C for 2 h, and then cool the mixture to 0 C.Filtration under reduced pressure and suction drying, the resulting white solid was recrystallized from absolute ethanol,Let stand overnight and dry in vacuum,85% yield(References: Ma Xianli, Li Fangyao, Duan Wengui, etc.Synthesis of camphor acid dihydrazide compound and its antibacterial activity [J] .Fine Industry, 2015,32 (12): 1426-1430.);
	With trifluoroacetic anhydride; In dichloromethane; at 18℃; for 3h;	To a mixture of (1R, 3S) -1, 2, 2-trimethylcyclopentane-1, 3-dicarboxylic acid (3.2 g, 15.98 mmol) in DCM (35 mL) was added 2, 2, 2-trifluoroacetic anhydride (16.78 g, 80 mmol) . The reaction mixture was stirred at 18 of 3 hours. The solvent was removed to afford the crude product (1R, 5S) -1, 8, 8-trimethyl-3-oxabicyclo [3.2.1] octane-2, 4-dione.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2243 - 2245
[2]Tetrahedron Asymmetry,2010,vol. 21,p. 519 - 523
[3]Patent: CN110590665,2019,A .Location in patent: Paragraph 0046-0049
[4]Tetrahedron Asymmetry,1996,vol. 7,p. 2551 - 2562
[5]Journal of Organic Chemistry,1990,vol. 55,p. 4051 - 4062
[6]Journal of Fluorine Chemistry,2000,vol. 105,p. 77 - 82
[7]Patent: WO2016/106623,2016,A1 .Location in patent: Page/Page column 129

9
[ 124-83-4 ]
[ 52730-21-9 ]

Reference： [1]South African Journal of Chemistry,1997,vol. 50,p. 22 - 27

11
[ 64-17-5 ]
[ 124-83-4 ]
[ 368423-74-9 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8509 - 8514

12
[ 124-83-4 ]
[ 88150-42-9 ]
(1R,3S)-camphoric acid salt of S-amlodipine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃; for 20h;Heating / reflux;	10 g of racemic amlodipine and 3.7 g of (lR,3S)-camphoric acid were added to 100 mL of isopropanol and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 20 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 2.8 g of (lR,3S)-camphoric acid salt of S-amlodipine. The obtained (lR,3S)-camphoric acid salt of S-amlodipine had a 2 : 1 molar ratio of S-amlodipine to (lR,3S)-camphoric acid, as confirmed by H NMR spectral analysis:[31] 1U NMR (CD OD, 300 MHz) 0.90 (s, 3H), 1.15 (m, 9H), 1.27 (s, 3H), 1.40(m,IH), 1.71 (m, IH), 2.10 (m, IH), 2.32 (s, 6H), 2.50(m, IH), 2.71 (m, IH), 3.09 (m, 4H), 3.57 (s, 6H), 3.70(m, 4H), 4.03 (m, 4H), 4.69 (q, 4H), 5.40 (s, 2H), 7.14(m, 6H), 7.38 (m, 2H)[32] 2.8 g of the obtained (lR,3S)-camphoric acid salt of S-amlodipine was added to 30 mL of dichloromethane and 30 mL of a 2N sodium hydroxide solution, stirred and allowed to stand to isolate a dichloromethane layer. 30 mL of dichloromethane was further added to the aqueous solution, stirred and allowed to stand to further isolate a dichloromethane layer. The obtained dichloromethane solution was dried using magnesium sulfate and concentrated under reduced pressure to yield 2.1 g of S- amlodipine.[33] 1H NMR (CD3OD, 300 MHz) 1.15 (t, 3H), 2.32 (s, 3H), 2.86 (t, 2H), 3.57 (m,5H), 4.05 (m, 2H), 4.67 (q, 2H), 5.39 (s, 2H), 7.14(m, 3H), 7.38 (m, IH)[34] Optical purity: S-amlodipine/R-amlodipine = 98.6/1.4[35] The solution was acidified using a 2N hydrochloric solution, and an organic layer was extracted twice from the solution using 100 mL of ethylacetate. The extracted organic layer was dried using magnesium sulfate and concentrated under reduced pressure to collect 0.49 g of (lR,3S)-camphoric acid. <n="7"/>[36] 1U NMR (DMSO-d6, 300 MHz) 0.75 (s, 3H), 1.12 (s, 3H), 1.18 (s, 3H), 1.36 (m,IH), 1.72 (m, IH), 1.96 (m, IH), 2.36 (m, IH), 2.72 (m, IH), 12.1 (s, 2H)

Reference： [1]Patent: WO2008/26838,2008,A1 .Location in patent: Page/Page column 5-6

13
(1R,3S)-camphoric acid salt of S-amlodipine [ No CAS ]
[ 124-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In dichloromethane; water;	10 g of racemic amlodipine and 3.7 g of (lR,3S)-camphoric acid were added to 100 mL of isopropanol and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 20 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 2.8 g of (lR,3S)-camphoric acid salt of S-amlodipine. The obtained (lR,3S)-camphoric acid salt of S-amlodipine had a 2 : 1 molar ratio of S-amlodipine to (lR,3S)-camphoric acid, as confirmed by H NMR spectral analysis:[31] 1U NMR (CD OD, 300 MHz) 0.90 (s, 3H), 1.15 (m, 9H), 1.27 (s, 3H), 1.40(m,IH), 1.71 (m, IH), 2.10 (m, IH), 2.32 (s, 6H), 2.50(m, IH), 2.71 (m, IH), 3.09 (m, 4H), 3.57 (s, 6H), 3.70(m, 4H), 4.03 (m, 4H), 4.69 (q, 4H), 5.40 (s, 2H), 7.14(m, 6H), 7.38 (m, 2H)[32] 2.8 g of the obtained (lR,3S)-camphoric acid salt of S-amlodipine was added to 30 mL of dichloromethane and 30 mL of a 2N sodium hydroxide solution, stirred and allowed to stand to isolate a dichloromethane layer. 30 mL of dichloromethane was further added to the aqueous solution, stirred and allowed to stand to further isolate a dichloromethane layer. The obtained dichloromethane solution was dried using magnesium sulfate and concentrated under reduced pressure to yield 2.1 g of S- amlodipine.[33] 1H NMR (CD3OD, 300 MHz) 1.15 (t, 3H), 2.32 (s, 3H), 2.86 (t, 2H), 3.57 (m,5H), 4.05 (m, 2H), 4.67 (q, 2H), 5.39 (s, 2H), 7.14(m, 3H), 7.38 (m, IH)[34] Optical purity: S-amlodipine/R-amlodipine = 98.6/1.4[35] The solution was acidified using a 2N hydrochloric solution, and an organic layer was extracted twice from the solution using 100 mL of ethylacetate. The extracted organic layer was dried using magnesium sulfate and concentrated under reduced pressure to collect 0.49 g of (lR,3S)-camphoric acid. <n="7"/>[36] 1U NMR (DMSO-d6, 300 MHz) 0.75 (s, 3H), 1.12 (s, 3H), 1.18 (s, 3H), 1.36 (m,IH), 1.72 (m, IH), 1.96 (m, IH), 2.36 (m, IH), 2.72 (m, IH), 12.1 (s, 2H)

Reference： [1]Patent: WO2008/26838,2008,A1 .Location in patent: Page/Page column 5-6

14
[ 124-83-4 ]
[ 88150-42-9 ]
C₁₀H₁₆O₄*2C₂₀H₂₅ClN₂O₅ [ No CAS ]
(1R,3S)-camphoric acid salt of S-amlodipine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃; for 17 - 22h;Heating / reflux;Product distribution / selectivity;	Example 2: Preparation (1) of diastereomeric salt from racemic amlodipine[38] 6.0 g of racemic amlodipine and 2.94 g of (lR,3S)-camphoric acid were added to 65 mL of isopropanol and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 22 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 1.51 g of (lR,3S)-camphoric acid salt of S-amlodipine. [39] Optical purity: S-amlodipine/R-amlodipine = 99.0/1.0[40] Example 3: Preparation (2) of diastereomeric salt from racemic amlodipine[41] 8.0 g of racemic amlodipine and 1.9 g of (lR,3S)-camphoric acid were added to 80 mL of isopropanol and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 17 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 2.36 g of (lR,3S)-camphoric acid salt of S-amlodipine. [42] Optical purity: S-amlodipine/R-amlodipine = 97.9/2.1
	In ethyl acetate; at 20℃; for 21h;Heating / reflux;Product distribution / selectivity;	10 g of racemic amlodipine and 1.23 g of (lR,3S)-camphoric acid were added to 70 mL of ethyl acetate and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 21 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 4.7 g of (lR,3S)-camphoric acid salt of S-amlodipine. [48] Optical purity: S-amlodipine/R-amlodipine = 98.9/1.1
	In acetonitrile; at 20℃; for 19 - 23h;Heating / reflux;Product distribution / selectivity;	Example 6: Preparation of S-amlodipine from racemic amlodipine[50] 10 g of racemic amlodipine and 1.23 g of (lR,3S)-camphoric acid were added to 75 mL of acetonitrile and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed <n="8"/>at room temperature for 23 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 5.5 g of (lR,3S)-camphoric acid salt of S-amlodipine. [51] Optical purity: S-amlodipine/R-amlodipine = 97.8/2.2[52] Example 7: Preparation of S-amlodipine from racemic amlodipine[53] 20 g of racemic amlodipine and 2.47 g of (lR,3S)-camphoric acid were added to160 mL of acetonitrile and heated to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 19 hours to precipitate crystals. The precipitated crystals were extracted to collect crystals. The collected crystals were added to 120 mL of acetonitrile to be dissolved, followed by slowly cooling down the resultant solution to room temperature. The solution was allowed to stand undisturbed at room temperature for 20 hours to precipitate crystals. The precipitated crystals were extracted, collected, and dried under reduced pressure, to yield 9.7 g of (lR,3S)-camphoric acid salt of S-amlodipine. [54] Optical purity: S-amlodipine/R-amlodipine = 99.98/0.02

Reference： [1]Patent: WO2008/26838,2008,A1 .Location in patent: Page/Page column 6
[2]Patent: WO2008/26838,2008,A1 .Location in patent: Page/Page column 6
[3]Patent: WO2008/26838,2008,A1 .Location in patent: Page/Page column 6-7

15
[ 124-83-4 ]
3C₁₀H₁₅O₄^(1-)*2Mg⁽²⁺⁾*NO₃^(1-)*3H₂O*C₂H₃N [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 13675 - 13682

16
[ 124-83-4 ]
[ 504-63-2 ]
Mg⁽²⁺⁾*2C₃H₈O₂*C₁₀H₁₄O₄^(2-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 13675 - 13682

17
[ 124-83-4 ]
[ 67111-66-4 ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 658 - 665
[2]Journal of the Chemical Society. Perkin transactions I,1983,p. 1465 - 1474
[3]Organic Syntheses,1993,vol. 71,p. 48 - 48

18
[ 124-83-4 ]
[ 67111-66-4 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 581 - 587

19
[ 887401-92-5 ]
[ 124-83-4 ]
[ 887401-95-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	In ethyl acetate; at 20℃; for 4h;	Example 6 Preparation of Camphoric Acid Salt (1R,3S)-1,2,2-Trimethylcyclopentane-1,3-dicarboxylic acid (0.846 g, 4.23 mmol) in ethyl acetate (20.0 mL) was slowly added to a solution of N-[2-({(3R)-1-[trans-4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)-benzamide (2.00 g, 3.84 mmol) in ethyl acetate (20.0 mL). After being stirred at room temperature for 4 h, the white precipitate was collected by vacuum filtration and the cake was washed with EtOAc (10 mL). The cake was dried under vacuum to constant weight to provide 2.46 g (89%) of N-[2-({(3R)-1-[trans-4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylate as a white crystalline solid. DSC and XRPD spectra are provided in FIGS. 5 and 6, respectively; Example 7; Properties of the Camphoric Acid Salt; A crystalline sample of N-[2-({(3R)-1-[4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide camphorate, prepared in a manner substantially according to Example 6, was shown to have the properties provided in Table 6. DSC and XRPD data are provided in FIGS. 5 and 6; Elemental Analysis Calc'd: C, 59.99; H, 6.57; N, 7.77; F, 7.91 Found: C, 59.69; H, 6.43; N, 7.56; F, 8.02 Water Content (Karl Fisher) 0.18% DSC ( C.) 173 (onset); 176 (peak)

Reference： [1]Patent: US2006/111404,2006,A1 .Location in patent: Page/Page column 11

20
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[ 7732-18-5 ]
[ 124-40-3 ]
2Cd⁽²⁺⁾*3C₁₀H₁₄O₄^(2-)*2(CH₃)2NH₂⁽¹⁺⁾*4(CH₃)2NH*2H₂O=[Cd₂(C₁₀H₁₄O₄)3]^(2-)*2(CH₃)2NH₂⁽¹⁺⁾*4(CH₃)2NH*2H₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 8388 - 8391

21
zinc(II) nitrate hexahydrate [ No CAS ]
[ 17252-51-6 ]
[ 124-83-4 ]
[Zn(D-camphorato)(trimethylenedipyridine)]*H₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6115 - 6118

22
[ 17252-51-6 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[ 952408-07-0 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6115 - 6118

23
[ 17252-51-6 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[ 952408-07-0 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6115 - 6118
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 6115 - 6118

24
[ 124-83-4 ]
[ 71125-38-7 ]
meloxicam:(+)-camphoric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;Product distribution / selectivity;	176 mg of <strong>[71125-38-7]meloxicam</strong> was ground with 100 mg of (+) camphoric acid and 400 muL of THF was added to the solid mixture. The solids gathered after grinding were stored in screw cap vials for subsequent analysis.

Reference： [1]Crystal Growth and Design,2010,vol. 10,p. 4401 - 4413
[2]Patent: US2009/203680,2009,A1 .Location in patent: Page/Page column 11

25
[ 753015-44-0 ]
[ 124-83-4 ]
[ 1228391-44-3 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	In isopropyl alcohol; at 20℃;Heating;	Example 31 : (R)-5-((E)-2-Pyrrolidin-3-ylvinyl)pyrimidine mono-(1R,2S)-(+)- Camphorate(1 R,2S)-(+)-Camphoric acid (1.149 g, 5.74 mmol) was added as a solid to a stirring, warm solution of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine free base (1.00 g, 5.70 mmol) in ethanol (14 mL) in a round-bottomed flask. Upon heating, all solids dissolved, affording a yellow solution. No precipitate forms upon standing at ambient temperature overnight. The solution was concentrated via rotary evaporation to an amber-brown foam that was dried under vacuum at 50 C (air bleed) for 6 h to give 2.098 g of a viscous, amber oil. lsopropyl acetate (10 mL) was added, and the solution was allowed to stand at ambient temperature overnight. There was some evidence of crystal nucleation in the gummy, red-amber oil. More isopropyl acetate (10 mL) and 2-propanol (20 drops) was added, and the mixture was gently heated and stirred over 48 h. The resulting milky, creamy solids with some orange lumps were broken with a spatula, and the mixture (colorless liquor) was stirred overnight. The off-white solids were filtered on a Bchner funnel, washed with cold isopropyl acetate (10 mL) and dried in a vacuum oven (air bleed) at 50 0C for 21 h to give 2.034 g (94.9%) of an off-white to cream colored powder, mp 157-159 0C. 1H NMR (DMSO-de) confirmed the 1 :1 salt stoichiometry. 1H NMR (DMSOd6): delta 9.00 (s, 1 H), 8.85 (s, 2H), 6.58 (dd, 1 H), 6.47 (d, 1 H), 3.17 (dd, 1 H), 3.08 (m, 1 H), 2.97 (m, 1 H), 2.92 (dd, 1 H) 2.74 (dd, 1 H), 2.61 (dd, 1 H), 2.30 (sextet, 1 H), 2.00 (m, 2H), 1.65 (m, 2H), 1.32 (m, 1 H), 1.15 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry), 1.07 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry), 0.75 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry).
94.9%	In ethanol;Heating;	(1 R,2S)-(+)-Camphoric acid (1.149 g, 5.74 mmol) was added as a solid to a stirring, warm solution of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine free base (1.00 g, 5.70 mmol) in ethanol (14 mL) in a round-bottomed flask. Upon heating, all solids dissolved, affording a yellow solution. No precipitate forms upon standing at ambient temperature overnight. The solution was concentrated via rotary evaporation to an amber-brown foam that was dried under vacuum at 50 C (air bleed) for 6 h to give 2.098 g of a viscous, amber oil. Isopropyl acetate (10 mL) was added, and the solution was allowed to stand at ambient temperature overnight. There was some evidence of crystal nucleation in the gummy, red-amber oil. More isopropyl acetate (10 mL) and 2-propanol (20 drops) was added, and the mixture was gently heated and stirred over 48 h. The resulting milky, creamy solids with some orange lumps were broken with a spatula, and the mixture (colorless liquor) was stirred overnight. The off-white solids were filtered on a Buchner funnel, washed with cold isopropyl acetate (10 mL) and dried in a vacuum oven (air bleed) at 50 C for 21 h to give 2.034 g (94.9%) of an off-white to cream colored powder, mp 157-159 C. 1H NMR (DMSO-d6) confirmed the 1 :1 salt stoichiometry. 1H NMR (DMSO-d6): delta 9.00 (s, 1 H), 8.85 (s, 2H), 6.58 (dd, 1 H), 6.47 (d, 1 H), 3.17 (dd, 1 H), 3.08 (m, 1 H), 2.97 (m, 1 H), 2.92 (dd, 1 H) 2.74 (dd, 1 H), 2.61 (dd, 1 H), 2.30 (sextet, 1 H), 2.00 (m, 2H), 1.65 (m, 2H), 1.32 (m, 1 H), 1.15 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry), 1.07 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry), 0.75 (s, 3H, -CH3 of acid moiety, indicating a mono-salt stoichiometry).

Reference： [1]Patent: WO2010/65443,2010,A1 .Location in patent: Page/Page column 49-50
[2]Patent: WO2011/112428,2011,A2 .Location in patent: Page/Page column 43-44

26
[ 67-56-1 ]
[ 124-83-4 ]
[ 29607-02-1 ]
[ 15797-21-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride; at 20℃; for 2h;	To a stirred solution of (lR,3S)-(+)-camphoric acid (5 g, 25 mmol) in 30 mL of methanol, anhydrous HCl was bubbled for 2 h at room temperature. Methanol was evaporated and the residue was mixed with 5% sodium bicarbonate solution until the effervescence ceased and then 5% sodium hydroxide was added. The diester byproduct was removed by extraction with diisopropyl ether. The aqueous layer was acidified with 10% HCl and extracted with diisopropyl ether. The combined ether extracts were dried over anhydrous sodium sulfate and evaporated to obtain (lR,3S)-3- (methoxycarbonyl)-l,2,2-trimethylcyclopentanecarboxylicacid (4.38 g) in 83% yield. 1H NMR (400MHz5 CDCl3) delta ppm 0.84 (s, 3H), 1.25 (s, 6H), 1.53-1.55 (m, IH), 1.80- 1.84 (m, IH), 2.19-2.22 (m, IH), 2.25-2.57 (m, IH), 2.79-2.84 (m, IH); 3.70 (s, 3H); m/z (M+l): 214.

Reference： [1]Patent: WO2010/79413,2010,A2 .Location in patent: Page/Page column 31-32

27
[ 124-83-4 ]
[ 71125-38-7 ]
[ 1246227-13-3 ]

Reference： [1]Crystal Growth and Design,2010,vol. 10,p. 4401 - 4413

28
bismuth (III) nitrate pentahydrate [ No CAS ]
[ 64-17-5 ]
[ 124-83-4 ]
[ 1310-73-2 ]
Bi4Na4(1R₃S-camphorate)8(ethanol)3.1(H₂O)3.4 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In water; at 100℃; for 72h;Autoclave; High pressure;	A mixture of Bi(NO3)3·5H2O (0.242 g, 0.5 mmol) and an excess of 1R3S-camphoric acid (1R3S-cam) (0.300 g, 1.5 mmol) and NaOH (0.024 g, 0.6 mmol) in EtOH (25 ml) was sealed in a Teflon-lined autoclave and heated to a temperature of 100 C for 3 day, and then cooled slowly at 0.1 C/min to room temperature. Colorless, needle-shaped crystals and white polycrystalline powder were obtained in quantitative yield based on bismuth. The products were washed with DMF to dissolve and remove any unreacted ligand. The final product was isolated by vacuum filtration. It is this mixture of powder and needle crystals that were used for structure and physical characterizations.

Reference： [1]Journal of Solid State Chemistry,2012,vol. 195,p. 94 - 100

29
[ 124-83-4 ]
[ 74-88-4 ]
[ 15797-21-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 3.5h;	Iodomethane (10.93 mL, 175 mmol) was added to a mixture of(lR,3S)- l,2,2-trimethylcyclopentane-l ,3-dicarboxylic acid (10.0 g, 49.9 mmol), potassium carbonate (41.4 g, 300 mmol) and dimethyl sulfoxide (50 mL) in a room temperature water bath. The resultant mixture was stirred at room temperature for 3.5 h, diluted with ethyl acetate (400 mL) and hexanes (400 mL), washed with water (3x200 mL), brine (100 mL), dried (MgS04) and filtered through a silica gel pad. The pad was rinsed with ethyl acetate (100 mL). The filtrate was concentrated to give the title compound (1 1.40 g, 100% yield). XH NMR (400 MHz, chloroform-if) delta ppm 3.69 (3 H, s), 3.68 (3 H, s), 2.80 (1 H, t, J=9.46 Hz), 2.58 (1 H, td, J=12.65, 7.48 Hz), 2.09-2.32 (1 H, m), 1.73-1.92 (1 H, m, J=13.86, 9.79, 9.79, 7.48 Hz), 1.51 (1 H, ddd, J=13.64, 9.57, 3.85 Hz), 1.25 (3 H, s), 1.20 (3 H, s), 0.76 (3 H, s); MS (ES+) m/z: 229.1 (M+H); HPLC retention time: 3.623 min (analytical HPLC Method F).

Reference： [1]Patent: WO2012/125886,2012,A1 .Location in patent: Page/Page column 104

30
[ 13160-06-0 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[ 7732-18-5 ]
[Cd(D-cam)(3-pna)(H₂O)₂]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydroxide; at 80℃; for 48h;Sealed tube;	2.2 Preparation of [Cd(dl-cam)(3-pina)]n (1) Cd(NO3)2·4H2O (85 mg, 0.28 mmol), d-camphoric acid (56 mg, 0.28 mmol) and 3-pna (55 mg, 0.28 mmol), along with a 0.5mL aliquot of 1.0M NaOH (0.5 mmol), were placed into 10 mL distilled H2O in a 15mL screw-cap vial. The vial was sealed and heated at 80C for 48h, whereupon it was cooled slowly to 25C. Colorless crystals of 1 (53 mg, 0.097 mmol, 35% yield based on Cd) were isolated after filtration and washing with deionized water and acetone. Anal. Calc. for C21H27CdN3O7 (1): C, 46.21; H, 4.96; N, 7.70. Found: C, 46.32; H, 4.72; N, 7.66%. IR (cm-1): 3250 (w, br), 2974 (m), 1651 (m), 1585 (m), 1531 (s), 1434 (m), 1421 (m), 1384 (m), 1358 (m), 1335 (m), 1289 (m), 1198 (m), 1119 (m), 1047 (m), 1029 (m), 804 (m), 743 (m).

Reference： [1]Inorganica Chimica Acta,2013,vol. 403,p. 136 - 141

31
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[ 39642-69-8 ]
[Cd(DL-cam)(3-pina)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium hydroxide; In water;	Cd(NO3)2·4H2O (85 mg, 0.28 mmol), 5 d-camphoric acid (56 mg, 0.28 mmol) and 3-pina (55 mg, 0.28 mmol), along with a 0.5 mL aliquot of 1.0 M NaOH (0.5 mmol), were placed into 10 mL distilled H2O in a 15 mL screw-cap vial. Colorless crystals of 2 (66 mg, 0.13 mmol, 46% yield based on Cd) were isolated after filtration and washing with deionized water and acetone. Anal. Calc. for C21H23CdN3O5 (2): C, 49.47; H, 4.55; N, 8.24. Found: C, 49.11; H, 4.04; N, 7.97%. IR (cm-1): 3300 (w), 2965 (w), 1698 (m), 1592 (m), 1525 (s), 1477 (m), 1431 (s), 1399 (s), 1331 (m), 1287 (s), 1051 (m), 1020 (m), 857 (m), 807 (s)

Reference： [1]Inorganica Chimica Acta,2013,vol. 403,p. 136 - 141

32
[ 582-60-5 ]
cadmium sulfate * 4 H₂O [ No CAS ]
[ 124-83-4 ]
[Cd₂(D-cam)₂(5,6-dimethylbenzimidazole)4]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine; In water; at 140℃; for 72h;High pressure;	CdSO4*4H2O (28 mg, 0.1 mmol), D-camphoric acid (20 mg,0.1 mmol), 5,6-dimethylbenzimidazole (15 mg, 0.1 mmol), triethylamine (25 muL) and H2O (8 mL) were combined in a 15-mL Teflon lined stainless steel container, which was heated at 140 C for 72 h and then cooled to room temperature at a rate of 10 C h-1. Colorless crystals of 1 were obtained in 46% yield based on Cd.

Reference： [1]Inorganica Chimica Acta,2013,vol. 405,p. 43 - 50

33
zinc(II) sulfate heptahydrate [ No CAS ]
[ 582-60-5 ]
[ 124-83-4 ]
[Zn₂(D-cam)₂(5,6-dimethylbenzimidazole)₂]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With triethylamine; In methanol; water; at 120℃; for 72h;High pressure;	ZnSO4*7H2O (29 mg, 0.1 mmol), D-camphoric acid (20 mg,0.1 mmol), 5,6-dimethylbenzimidazole (15 mg, 0.1 mmol), triethylamine (25 muL), methanol (4 mL) and H2O (4 mL) were combined in a 15-mL Teflon-lined stainless steel container, which was heated at 120 C for 72 h and then cooled to room temperature at a rate of 10 C h-1. Colorless crystals of 2 were obtained in 44% yield based on Zn.

Reference： [1]Inorganica Chimica Acta,2013,vol. 405,p. 43 - 50

34
[ 582-60-5 ]
[ 124-83-4 ]
cobalt(II) perchlorate hexahydrate [ No CAS ]
[Co(D-cam)_1/2(L-cam)_1/2(5,6-dimethylbenzimidazole)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine; In water; at 160℃; for 72h;High pressure;	Co(ClO4)2*6H2O (37 mg, 0.1 mmol), <strong>[124-83-4]D-(+)-camphoric acid</strong> (20 mg, 0.1 mmol), 5,6-dimethylbenzimidazole (15 mg, 0.1 mmol), triethylamine (25 lL) and H2O (8 mL) were combined in a 15-mL Teflon-lined stainless steel container, which was heated at 160 Cfor 72 h and then cooled to room temperature at a rate of 10 C h-1. Dark purple crystals of 3 were obtained in 35% yield based on Co.

Reference： [1]Inorganica Chimica Acta,2013,vol. 405,p. 43 - 50

35
[ 67-56-1 ]
europium(III) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[Eu(cam)(MeOH)₂(NO₃)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	at 120℃; for 48h;High pressure;	General procedure: Compounds Pr·1-Eu·4 were obtained in a solvothermal conditions, a mixture of Ln(NO3)3·6H2O (0.358mmol) (Ln=Pr, Nd, Sm, and Er), d-H2cam (0.125mmol), MeOH (6mL) was placed in a Teflon reactor (25mL) and heated at 120C for two days. After the mixture was gradually cooled to room temperature at a rate of 1Ch-1, single crystals of compounds suitable for X-ray study were obtained. The solid product was washed with MeOH and isolated by suction filtration. A powder X-ray diffraction pattern of the bulk sample compared well with the pattern simulated from the single-crystal data (vide infra).

Reference： [1]Polyhedron,2013,vol. 66,p. 34 - 38

36
[ 67-56-1 ]
praseodymium(III) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[Pr(cam)(MeOH)₂(NO₃)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	at 120℃; for 48h;High pressure;	General procedure: Compounds Pr·1-Eu·4 were obtained in a solvothermal conditions, a mixture of Ln(NO3)3·6H2O (0.358mmol) (Ln=Pr, Nd, Sm, and Er), d-H2cam (0.125mmol), MeOH (6mL) was placed in a Teflon reactor (25mL) and heated at 120C for two days. After the mixture was gradually cooled to room temperature at a rate of 1Ch-1, single crystals of compounds suitable for X-ray study were obtained. The solid product was washed with MeOH and isolated by suction filtration. A powder X-ray diffraction pattern of the bulk sample compared well with the pattern simulated from the single-crystal data (vide infra).

Reference： [1]Polyhedron,2013,vol. 66,p. 34 - 38

37
[ 67-56-1 ]
neodymium(III) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[Nd(cam)(MeOH)₂(NO₃)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	at 120℃; for 48h;High pressure;	General procedure: Compounds Pr·1-Eu·4 were obtained in a solvothermal conditions, a mixture of Ln(NO3)3·6H2O (0.358mmol) (Ln=Pr, Nd, Sm, and Er), d-H2cam (0.125mmol), MeOH (6mL) was placed in a Teflon reactor (25mL) and heated at 120C for two days. After the mixture was gradually cooled to room temperature at a rate of 1Ch-1, single crystals of compounds suitable for X-ray study were obtained. The solid product was washed with MeOH and isolated by suction filtration. A powder X-ray diffraction pattern of the bulk sample compared well with the pattern simulated from the single-crystal data (vide infra).

Reference： [1]Polyhedron,2013,vol. 66,p. 34 - 38

38
[ 67-56-1 ]
samarium(III) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[Sm(cam)(MeOH)₂(NO₃)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	at 120℃; for 48h;High pressure;	General procedure: Compounds Pr·1-Eu·4 were obtained in a solvothermal conditions, a mixture of Ln(NO3)3·6H2O (0.358mmol) (Ln=Pr, Nd, Sm, and Er), d-H2cam (0.125mmol), MeOH (6mL) was placed in a Teflon reactor (25mL) and heated at 120C for two days. After the mixture was gradually cooled to room temperature at a rate of 1Ch-1, single crystals of compounds suitable for X-ray study were obtained. The solid product was washed with MeOH and isolated by suction filtration. A powder X-ray diffraction pattern of the bulk sample compared well with the pattern simulated from the single-crystal data (vide infra).

Reference： [1]Polyhedron,2013,vol. 66,p. 34 - 38

39
zinc(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 220593-43-1 ]
[Zn₂(camphoric acid-2H)2(1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With lithium hydroxide monohydrate In water at 140℃; for 72h; Autoclave; High pressure;

Reference： [1]Liu; Liu [Russian Journal of Coordination Chemistry, 2014, vol. 40, # 4, p. 232 - 239][Koord. Khim., 2014, vol. 40, # 4, p. 232 - 239,8]

40
copper(II) nitrate trihydrate [ No CAS ]
[ 124-83-4 ]
[ 39677-03-7 ]
[Cu^I(1,1-(1,4-butanediyl)bis(1H-benzimidazole))₂](HCOO) [ No CAS ]
[Cu^II(OH)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))(H₂O)]₂(NO₃)₂*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%; 25%	With sodium hydroxide; In water; at 120℃; for 97h;Autoclave;	A mixture of Cu(NO3)2.3H2O (0.024 g, 0.1 mmol), D-H2cam(0.020 g, 0.1 mmol), bbbm (0.015 g, 0.05 mmol), H2O (10 mL) and NaOH (0.1 mol L1, 2 mL) was stirred for 1 h in air, and then sealedin a 25 mL Teflon-lined stainless-steel autoclave at 120 C for 96 h. After slowly cooling to room temperature, blue block crystals of 4 and yellow block crystals of 5 were obtained. For 4, yield: 25%(based on Cu). Anal. Calc. for C18H23CuN5O6 (468.94): C, 46.10; H,4.94; N, 14.93. Found: C, 45.95; H, 4.91; N, 14.84%. IR (KBr,cm1): 3423 m, 3103 w, 2950 w, 2361 w, 1613 w, 1518 m, 1464m, 1385 s, 1295 w, 1259 w, 1199 w, 1011 w, 754 m, 636 w, 510w, 431 w. For 5, yield: 18% (based on Cu). Anal. Calc. forC37H37CuN8O2 (689.29): C, 64.47; H, 5.41; N, 16.26. Found: C,64.35; H, 5.37; N, 16.18%. IR (KBr, cm1): 3441 m, 2940 w, 2361w, 1613 w, 1531 m, 1467 m, 1385 s, 1351 s, 1323 s, 1265 w,1230 m, 1153 w, 927 w, 860 w, 769 m, 628 w, 513 w, 426 w.

Reference： [1]Inorganica Chimica Acta,2014,vol. 419,p. 111 - 117

41
nickel(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 39677-03-7 ]
[Ni(D-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))][Ni(L-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium hydroxide; In water; at 120℃;Autoclave;	General procedure: A mixture of Cu(NO3)2·3H2O (0.024 g, 0.1 mmol), D-H2cam (0.020 g, 0.1 mmol), bbbm (0.015 g, 0.05 mmol), H2O (10 mL) and NaOH (0.1 mol L-1, 2 mL) was stirred for 1 h in air, and then sealed in a 25 mL Teflon-lined stainless-steel autoclave at 120 C for 96 h. After slowly cooling to room temperature, blue block crystals of 4 and yellow block crystals of 5 were obtained. The synthetic procedures of green block crystalsof 2 and colorless block crystals of 3 are similar to that of 1, exceptthat Ni(NO3)2.6H2O and Zn(NO3)2.6H2O were used, respectively.For 1, yield: 65% (based on Co). Anal. Calc. for C28H32CoN4O4(547.51): C, 61.42; H, 5.89; N, 10.23. Found: C, 64.35; H, 5.84; N,10.14%. IR (KBr, cm1): 3438 m, 2968 m, 2361 m, 1542 s, 1515 s,1461 s, 1407 s, 1395 s, 1294 m, 1245 m, 1198 m, 1129 w, 1009w, 917 w, 810 w, 745 s, 677 w, 611 w, 515 w, 428 w. For 2, yield:45% (based on Ni). Anal. Calc. for C28H32NiN4O4 (547.27): C, 61.45;H, 5.89; N, 10.24. Found: C, 64.32; H, 5.83; N, 10.12%. IR (KBr,cm1): 3440 m, 2966 m, 2361 m, 1522 s, 1460 s, 1419 s, 1367 m,1293 m, 1244 m, 1198 m, 1130 w, 1009 w, 918 w, 812 w, 744 s,678 w, 610 w, 517 w, 428 w. For 3, yield: 50% (based on Zn). Anal.Calc. for C28H32ZnN4O4 (553.95): C, 60.71; H, 5.82; N, 10.11. Found:C, 60.55; H, 5.81; N, 10.02%. IR (KBr, cm1): 3437 m, 2967 m, 2361m, 1599 s, 1518 s, 1460 s, 1388 s, 1298 m, 1246 m, 1199 m, 1129 w,1010 w, 920 w, 807 w, 746 s, 677 w, 612 w, 514 w, 428 w.

Reference： [1]Inorganica Chimica Acta,2014,vol. 419,p. 111 - 117

42
zinc(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 39677-03-7 ]
[Zn(D-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))][Zn(L-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydroxide; In water; at 120℃;Autoclave;	General procedure: A mixture of Cu(NO3)2·3H2O (0.024 g, 0.1 mmol), D-H2cam (0.020 g, 0.1 mmol), bbbm (0.015 g, 0.05 mmol), H2O (10 mL) and NaOH (0.1 mol L-1, 2 mL) was stirred for 1 h in air, and then sealed in a 25 mL Teflon-lined stainless-steel autoclave at 120 C for 96 h. After slowly cooling to room temperature, blue block crystals of 4 and yellow block crystals of 5 were obtained. The synthetic procedures of green block crystalsof 2 and colorless block crystals of 3 are similar to that of 1, exceptthat Ni(NO3)2.6H2O and Zn(NO3)2.6H2O were used, respectively.For 1, yield: 65% (based on Co). Anal. Calc. for C28H32CoN4O4(547.51): C, 61.42; H, 5.89; N, 10.23. Found: C, 64.35; H, 5.84; N,10.14%. IR (KBr, cm1): 3438 m, 2968 m, 2361 m, 1542 s, 1515 s,1461 s, 1407 s, 1395 s, 1294 m, 1245 m, 1198 m, 1129 w, 1009w, 917 w, 810 w, 745 s, 677 w, 611 w, 515 w, 428 w. For 2, yield:45% (based on Ni). Anal. Calc. for C28H32NiN4O4 (547.27): C, 61.45;H, 5.89; N, 10.24. Found: C, 64.32; H, 5.83; N, 10.12%. IR (KBr,cm1): 3440 m, 2966 m, 2361 m, 1522 s, 1460 s, 1419 s, 1367 m,1293 m, 1244 m, 1198 m, 1130 w, 1009 w, 918 w, 812 w, 744 s,678 w, 610 w, 517 w, 428 w. For 3, yield: 50% (based on Zn). Anal.Calc. for C28H32ZnN4O4 (553.95): C, 60.71; H, 5.82; N, 10.11. Found:C, 60.55; H, 5.81; N, 10.02%. IR (KBr, cm1): 3437 m, 2967 m, 2361m, 1599 s, 1518 s, 1460 s, 1388 s, 1298 m, 1246 m, 1199 m, 1129 w,1010 w, 920 w, 807 w, 746 s, 677 w, 612 w, 514 w, 428 w.

Reference： [1]Inorganica Chimica Acta,2014,vol. 419,p. 111 - 117

43
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 39677-03-7 ]
[Co(D-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))][Co(L-camphoric acid)(1,1-(1,4-butanediyl)bis(1H-benzimidazole))] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In water; at 120℃; for 97h;Autoclave;	A mixture of Cu(NO3)2·3H2O (0.024 g, 0.1 mmol), D-H2cam (0.020 g, 0.1 mmol), bbbm (0.015 g, 0.05 mmol), H2O (10 mL) and NaOH (0.1 mol L-1, 2 mL) was stirred for 1 h in air, and then sealed in a 25 mL Teflon-lined stainless-steel autoclave at 120 C for 96 h. After slowly cooling to room temperature, blue block crystals of 4 and yellow block crystals of 5 were obtained. The synthetic procedures of green block crystalsof 2 and colorless block crystals of 3 are similar to that of 1, exceptthat Ni(NO3)2.6H2O and Zn(NO3)2.6H2O were used, respectively.For 1, yield: 65% (based on Co). Anal. Calc. for C28H32CoN4O4(547.51): C, 61.42; H, 5.89; N, 10.23. Found: C, 64.35; H, 5.84; N,10.14%. IR (KBr, cm1): 3438 m, 2968 m, 2361 m, 1542 s, 1515 s,1461 s, 1407 s, 1395 s, 1294 m, 1245 m, 1198 m, 1129 w, 1009w, 917 w, 810 w, 745 s, 677 w, 611 w, 515 w, 428 w. For 2, yield:45% (based on Ni). Anal. Calc. for C28H32NiN4O4 (547.27): C, 61.45;H, 5.89; N, 10.24. Found: C, 64.32; H, 5.83; N, 10.12%. IR (KBr,cm1): 3440 m, 2966 m, 2361 m, 1522 s, 1460 s, 1419 s, 1367 m,1293 m, 1244 m, 1198 m, 1130 w, 1009 w, 918 w, 812 w, 744 s,678 w, 610 w, 517 w, 428 w. For 3, yield: 50% (based on Zn). Anal.Calc. for C28H32ZnN4O4 (553.95): C, 60.71; H, 5.82; N, 10.11. Found:C, 60.55; H, 5.81; N, 10.02%. IR (KBr, cm1): 3437 m, 2967 m, 2361m, 1599 s, 1518 s, 1460 s, 1388 s, 1298 m, 1246 m, 1199 m, 1129 w,1010 w, 920 w, 807 w, 746 s, 677 w, 612 w, 514 w, 428 w.

Reference： [1]Inorganica Chimica Acta,2014,vol. 419,p. 111 - 117

44
[ 124-83-4 ]
[ 89972-77-0 ]
zinc(II) oxide [ No CAS ]
2Zn⁽¹⁺⁾*2C₁₀H₁₄O₄^(2-)*2C₂₂H₁₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In water; at 155℃; for 72h;Autoclave;	A mixture of ZnO (0.008 g, 0.1 mmol), D-H2Cam (0.020 g,0.1 mmol), ttpy (0.032 g, 0.1 mmol), and H2O (8 mL) was sealed into a Teflon-lined stainless autoclave, heated at155C for three days and then cooled to room temperaturegradually. Yellow needle crystals were obtained, washed with methanol, and dried in air (yield 57%, 67 mg based on Zn).Selected IR (KBr, y cm1): 3061(w), 2961(m), 2877(w), 1613(s), 1580(s), 1476(m), 1389(m), 1358(m), 1163(m), 1125(w), 1013(m), 792(s), 731(m), 504(m). Anal. Calcd. forC64H62N6O8Zn2: C, 65.62; H, 5.34; N, 7.18. Found: C,65.99; H, 5.27; N, 7.42%.

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2015,vol. 45,p. 572 - 580

45
[ 66-71-7 ]
[ 124-83-4 ]
zinc(II) oxide [ No CAS ]
2Zn⁽¹⁺⁾*2C₁₀H₁₄O₄^(2-)*2C₁₂H₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In water; at 155℃; for 72h;Autoclave;	General procedure: A mixture of ZnO (0.008 g, 0.1 mmol), D-H2Cam (0.020 g,0.1 mmol), ttpy (0.032 g, 0.1 mmol), and H2O (8 mL) wassealed into a Teflon-lined stainless autoclave, heated at 155C for three days and then cooled to room temperaturegradually. Yellow needle crystals were obtained, washed withmethanol, and dried in air (yield 57%, 67 mg based on Zn).

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2015,vol. 45,p. 572 - 580

46
[ 124-83-4 ]
(4S)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one [ No CAS ]
(4S)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one monocamphorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93 mg	In water; acetone; at 20 - 40℃; for 20.5h;	Example 140 (4S)-4-Amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one monocamphorate monohydrate To the compound (100 mg) obtained in step 2 of Example 81, camphoric acid (39 mg), acetone (1.8 ml), and water (200 mul) were added at room temperature. The mixture was stirred at 40 C. for 20 hours and further stirred at room temperature for 0.5 hours. The deposited solid was collected by filtration to obtain the title compound (93 mg). 1H-NMR (DMSO-d6) delta: 0.77 (3H, s), 1.12 (3H, s), 1.18 (3H, s), 1.33-1.40 (1H, m), 1.66-1.77 (1H, m), 1.93-2.02 (1H, m), 2.24 (1H, dd, J=16.3, 4.2 Hz), 2.29-2.39 (1H, m), 2.69-2.79 (2H, m), 3.24 (3H, s), 3.49 (1H, dd, J=9.7, 3.6 Hz), 3.64-3.70 (1H, m), 4.00 (1H, dd, J=9.7, 6.0 Hz), 4.83 (2H, s), 7.05-7.15 (4H, m), 7.35-7.42 (1H, m), 7.69 (2H, d, J=8.5 Hz), 7.90 (1H, d, J=9.7 Hz), 7.95 (1H, s), 8.07 (2H, d, J=8.5 Hz). Anal. Calcd for C24H23FN6O.C10H16O4.H2O: C, 62.95; H, 6.37; F, 2.93; N, 12.95. Found: C, 62.44; H, 6.25; F, 3.37; N, 13.01.
93 mg	In water; acetone; at 20 - 40℃; for 20.5h;	To the compound (100 mg) obtained in step 2 of Example 81, camphoric acid (39 mg), acetone (1.8 ml), and water (200 mul) were added at room temperature. The mixture was stirred at 40 C. for 20 hours and further stirred at room temperature for 0.5 hours. The deposited solid was collected by filtration to obtain the title compound (93 mg). (0730) 1H-NMR (DMSO-d6) delta: 0.77 (3H, s), 1.12 (3H, s), 1.18 (3H, s), 1.33-1.40 (1H, m), 1.66-1.77 (1H, m), 1.93-2.02 (1H, m), 2.24 (1H, dd, J=16.3, 4.2 Hz), 2.29-2.39 (1H, m), 2.69-2.79 (2H, m), 3.24 (3H, s), 3.49 (1H, dd, J=9.7, 3.6 Hz), 3.64-3.70 (1H, m), 4.00 (1H, dd, J=9.7, 6.0 Hz), 4.83 (2H, s), 7.05-7.15 (4H, m), 7.35-7.42 (1H, m), 7.69 (2H, d, J=8.5 Hz), 7.90 (1H, d, J=9.7 Hz), 7.95 (1H, s), 8.07 (2H, d, J=8.5 Hz). (0731) Anal. Calcd for C24H23FN6O-C10H16O4.H2O: C, 62.95; H, 6.37; F, 2.93; N, 12.95. (0732) Found: C, 62.44; H, 6.25; F, 3.37; N, 13.01.

Reference： [1]Patent: US2015/51190,2015,A1 .Location in patent: Paragraph 0673-0677
[2]Patent: US2016/46639,2016,A1 .Location in patent: Paragraph 0729; 0730; 0731; 0732

47
(+/-)-2-amino-2-ethylhexan-1-ol [ No CAS ]
[ 124-83-4 ]
(R)-2-amino-2-ethylhexanol (1R,3S)-(+)-camphor acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.549 g	With triethylamine; In ethyl acetate; acetonitrile; at 25 - 50℃; for 2h;	0.508 g (3.50 mmol) of (R) -2-amino-2-ethylhexanol (89% ee)Was added ethyl acetate (5 mL),Acetonitrile (5 mL), 0.705 g (3.52 mmol) of (1 R, 3 S) - (+) - camphoric acid was added and kept at 50 C. for 1 hour. After cooling to 25 C. and aging for 1 hour, the solid was filtered off under reduced pressure. The solid was washed twice with ethyl acetate (5 mL) and then dried under reduced pressure at 40 C. to give the title compound (0.549 g, 97% ee, R-isomer recovery rate 67%). NMR confirmed that (R) -2-amino-2-ethylhexanol and (1R, 3S) - (+) - camphoric acid formed a salt at 2: 1 (molar ratio).

Reference： [1]Patent: JP2015/3861,2015,A .Location in patent: Paragraph 0127

48
[ 846589-98-8 ]
[ 124-83-4 ]
(R)-lorcaserin hydrochloride (1R,3S)-(+)-camphoric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	at 20 - 25℃;Reflux;	In a test tube were added (R)-Lorcaserin hydrochloride (86.6 mg, 0.373 mmols), (1R,3S)-(+)-camphoric acid (148.9 mg, 0.744 mmols, 2 eq.) and isobutyl acetate (0.86 mL,10v). Then, the resulting mixture was stirred for 15 minutes under reflux before cooling slowly to room temperature. Then, the suspension was stirred at room temperature overnight. The resulting solid was filtered in a sintered funnel (no.4), washed with cold isobutanol (0.5 mL) and dried at RT under high vacuum. 130.9 mg of Form B (81% yield) were obtained.

Reference： [1]Patent: WO2017/144598,2017,A1 .Location in patent: Page/Page column 6; 21

49
[ 124-83-4 ]
(R)-lorcaserin hydrochloride (+)-di-p-toluoyl-D-tartaric acid [ No CAS ]
(R)-lorcaserin hydrochloride (1R,3S)-(+)-camphoric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		In a round botton 10 mL flask, cocrystal of (R)-Lorcaserin hydrochloride with (+)-di-p-toluoyl-D-tartaric acid Form A (300.2 mg, 0.353 mmol) was dissolved in a biphasic mixture of ethyl acetate I water (1:1, 20 vol.). Then the aqueous phase was recovered and basified with sodium hydroxide 1 M to reach pH 10 and the resulting mixture was extracted with methyl isobutyl ketone (3 x 3 mL, 3 x 10 v). The organic phase was evaporated undervacuum to dryness. The resulting oil was dissolved in methyl isobutyl ketone (0.5 mL, 1.67 v) before adding successively (1R, 3S)-(+)-camphoric acid (424.6 mg, 2.118 mmols) and 704 pL (0.704 mmol) of hydrochloric acid 1 M dissolved in ethyl acetate. The reaction mixture was seeded with the Form B and was left stirring at room temperature until a solid precipitated. Then, the reaction mixture was cooled in an ice bath for 1 hour. Thesolid was recovered by filtration, washed twice with cold methyl isobutyl ketone (0.1 mL,0.33 v) and dried at RT under high vacuum. 224.8 mg of cocrystal of (R)-Lorcaserin hydrochloride and camphoric acid Form B (74% yield) were obtained as confirmed by XRPD. HPLC revealed an ee of 99.0%.

Reference： [1]Patent: WO2017/144598,2017,A1 .Location in patent: Page/Page column 6; 21; 22

50
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 76851-55-3 ]
[ 124-83-4 ]
[ 7732-18-5 ]
[Cd₂(D-camphorate)₂(3-bpmp)(H₂O)₂]_n [ No CAS ]
[Cd₂(DL-camphorate)₂(3-bpmp)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydroxide; at 120℃; for 48h;Sealed tube;	Cd(NO3)2·4H2O (226mg, 0.73mmol), D-camphoric acid (146mg, 0.73mmol), 3-bpmp (98mg, 0.37mmol), and 1.5mL of a 1.0M NaOH solution were mixed with 10mL of distilled H2O in a 23mL Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120C for 48h, and then was cooled slowly to 25C. Colorless crystals of 2 (80mg, 47% yield based on Cd) were isolated after washing with distilled water, ethanol, and acetone and drying in air. A few large block crystals of 3 were removed by manual separation. Running the reaction at 100C resulted in phase-pure samples of 2. Anal. Calc. for C36H48Cd2N4O8 2: C, 48.60; H, 5.44; N, 6.30% Found: C, 48.68; H, 4.82; N, 6.19%. IR (cm-1): 3000 (w, br), 1530(s), 1481(w), 1458(w), 1425(w), 1398(m), 1366(m), 1305(w), 1291(w), 1121(w), 1060(w), 997(w), 924(w), 835(m), 793(s), 758(m), 704(s).

Reference： [1]Inorganica Chimica Acta,2018,vol. 479,p. 10 - 16

51
[ 39642-75-6 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 124-83-4 ]
[Cd(D-camphorate)(N,N'-(hexane-1,6-diyl)diisonicotinamide)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With sodium hydroxide; In water; at 120℃; for 48h;Sealed tube;	Cd(NO3)2·4H2O (113mg, 0.37mmol), D-camphoric acid (73mg, 0.37mmol), hdn (119mg, 0.37mmol), and 0.75mL of a 1.0M NaOH solution were mixed with 10mL of distilled H2O in a 23mL Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120C for 48h, and then was cooled slowly to 25C. Colorless crystals of 1 (26mg, 11% yield based on Cd) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C28H36CdN4O6 1: C, 52.79; H, 5.70; N, 8.80% Found: C, 52.84; H, 5.61; N, 8.69%. IR (cm-1): 2962(w), 1674(w), 1576(s), 1403(s), 1323(w), 1098(m), 1013(m), 801(m), 698(m).

Reference： [1]Inorganica Chimica Acta,2018,vol. 479,p. 10 - 16

52
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 357429-12-0 ]
[ 124-83-4 ]
[Cd₂(DL-camphorate)₂(4-bpmp)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium hydroxide; In water; at 120℃; for 48h;Sealed tube;	Cd(NO3)2·4H2O (113mg, 0.37mmol), d-camphoric acid (73mg, 0.37mmol), 4-bpmp (98mg, 0.37mmol), and 0.75mL of a 1.0M NaOH solution were mixed with 10mL of distilled H2O in a 23mL Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120C for 48h, and then was cooled slowly to 25C. Straw-colored crystals of 4 (46mg, 28% yield based on Cd) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C36H48Cd2N4O8 4: C, 48.60; H, 5.44; N, 6.30% Found: C, 48.76; H, 5.41; N, 6.34%. IR (cm-1): 2961(w), 1578(s), 1396(s), 1363(m), 1326(m), 1093(m), 1013(m), 842(m), 801(s), 782(m), 698(m).

Reference： [1]Inorganica Chimica Acta,2018,vol. 479,p. 10 - 16

53
3,6-bis(1H-benzo[d]imidazol-1-yl)pyridazine [ No CAS ]
zinc(II) tetrafluoroborate monohydrate [ No CAS ]
[ 124-83-4 ]
Zn⁽²⁺⁾*H₂O*C₁₈H₁₂N₆*C₁₀H₁₄O₄^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 42%	With sodium hydroxide; In water; at 140℃; for 12h;Autoclave; High pressure;	The mixture of Zn(BF4)2·H2O (0.1mmol, 26.0mg), L2 (0.1mmol, 31.2mg), D-H2CAM (20.0mg, 0.1mmol), NaOH (8mg) in H2O (8mL) were placed in a 25mL Teflon-lined autoclave, and heated at 140C for 12h, and then cooled to environment temperature. Orange nubby crystals of 3 were collected and washed with water and methanol. Yield: ~42% (based on L2). Elemental analysis (%): Anal. Calcd for C28H28N6O5Zn: C, 56.49; H, 4.67; N, 14.01. Found: C, 56.62; H, 4.75; N, 14.14. IR (cm-1, KBr pellets): 3127(w), 2960(w), 2881(w), 2360(w), 1910(w), 1566(s), 1529(m), 1503(m), 1455(s), 1438(s), 1382(s), 1356(s), 1313(s), 1283(m), 1254(m), 1220(m), 1196(m), 976(w), 913(w), 762(m), 731(s), 619(m).

Reference： [1]Journal of Solid State Chemistry,2019,vol. 270,p. 379 - 387

54
[ 124-83-4 ]
[ 700-63-0 ]
C₁₀H₁₆O₄*C₈H₁₀N₂O [ No CAS ]

Reference： [1]Crystal Growth and Design,2019,vol. 19,p. 3652 - 3659

55
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 7732-18-5 ]
[ 49807-92-3 ]
[Co₂(DL-camphorate)₂(N,N′-(ethane-1,2-diyl)dinicotinamide)]·2H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydroxide; at 120℃; for 48h;High pressure; Autoclave;	Co(NO3)2·6H2O (107 mg, 0.37 mmol), D-camphoric acid (73 mg,0.37 mmol), and edn (99 mg, 0.37 mmol), and 0.75 mL of a 1.0 M NaOH solution were mixed with 10 mL of distilled H2O in a 23 mL Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120 C for 48 h, and then was cooled slowly to 25 C. Magenta crystals of 1 (25 mg, 16% yield based on Co) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C34H46Co2N4O12 1: C, 49.76; H, 5.65; N, 6.83% Found: C, 50.14; H,5.48; N, 6.84%. IR (cm-1): 3299 (w), 2960 (w), 1649 (m), 1581 (s),1550 (s), 1403 (s), 1368 (m), 1325 (m), 1301 (m), 1195 (w), 1167 (w),1109 (w), 1056 (w), 1038 (w), 887(w), 835 (w), 802 (w), 783 (w), 758(w), 694 (m).

Reference： [1]Inorganica Chimica Acta,2019,vol. 498

56
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
N,N′-(pentane-1,5-diyl)diisonicotinamide [ No CAS ]
[ 7732-18-5 ]
[Co₂(DL-camphorate)₂(N,N′-(butane-1,4-diyl)diisonicotinamide)]·2H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With sodium hydroxide; at 120℃; for 48h;High pressure; Autoclave;	Co(OAc)2·4H2O (92 mg, 0.37 mmol), D-camphoric acid (73 mg,0.37 mmol), and pedin (114 mg, 0.37 mmol), and 0.75 mL of a 1.0 M NaOH solution were mixed with 10 mL of distilled H2O in a 23 mLTeflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120 C for 48 h, and then was cooled slowly to 25 C. Magenta crystals of 4 (35 mg, 22% yield based on Co) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C37H52Co2N4O12 4: C, 51.51; H, 6.08; N, 6.49%Found: C, 50.78; H, 6.01; N, 6.13%. IR (cm-1): 3300(w, br), 1674(s),1540(s), 1415(m), 1301(w), 1053(w), 852(m), 797(w), 764(w), 684(w).

Reference： [1]Inorganica Chimica Acta,2019,vol. 498

57
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[ 6631-22-7 ]
[Co(D-camphorate)(N,N′-(ethane-1,2-diyl)dinicotinamide)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With sodium hydroxide; In water; at 120℃; for 48h;High pressure; Autoclave;	Co(NO3)2·6H2O (107 mg, 0.37 mmol), D-camphoric acid (73 mg,0.37 mmol), and edin (99 mg, 0.37 mmol), and 0.75 mL of a 1.0 M NaOH solution were mixed with 10 mL of distilled H2O in a 23 mLTeflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120 C for 48 h, and then was cooled slowly to 25 C. Magenta crystals of 2 (26 mg, 13% yield based on Co) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C24H28CoN4O6 2: C, 54.65; H, 5.35; N, 10.62% Found: C, 54.84; H, 5.29; N, 10.56%. IR (cm-1): 2962(w), 1660(m),1577(w), 1525(s), 1461(m), 1403(s), 1363(w), 1321(w), 1293(w),1086(m), 997(w), 861(w), 836(w), 802(s), 697(s), 666(w).

Reference： [1]Inorganica Chimica Acta,2019,vol. 498

58
[ 39642-75-6 ]
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 124-83-4 ]
[Co(D-camphorate)(N,N′-(hexane-1,6-diyl)diisonicotinamide)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With sodium hydroxide; In water; at 120℃; for 48h;High pressure; Autoclave;	Co(NO3)2·6H2O (107 mg, 0.37 mmol), D-camphoric acid (73 mg,0.37 mmol), and hdin (119 mg, 0.37 mmol), and 0.75 mL of a 1.0 M NaOH solution were mixed with 10 mL of distilled H2O in a 23 mLTeflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120 C for 48 h, and then was cooled slowly to 25 C. Magenta crystals of 5 (41 mg, 19% yield based on Co) were isolated after washing with distilled water, ethanol, and acetone and drying in air. Anal. Calc. for C28H34CoN4O6 5: C, 57.83; H, 5.89; N, 9.63% Found: C, 58.15; H, 6.00; N, 10.37%. IR (cm-1): 2961(w), 1640 (m), 1577(s),1401(s), 1364(m), 1325(w), 1098(m), 1013(w), 802(m), 698(m).

Reference： [1]Inorganica Chimica Acta,2019,vol. 498

59
copper(II) choride dihydrate [ No CAS ]
[ 69506-86-1 ]
[ 124-83-4 ]
2C₁₀H₁₄O₄^(2-)*2Cu⁽²⁺⁾*C₁₀H₁₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide; In water; at 160℃; for 80h;pH 6.0;Autoclave;	General procedure: A mixture of CuCl2·2H2O (85 mg, 0.50 mmol), H2DCA (99 mg, 0.50 mmol) and bimb (96 mg, 0.50 mmol) was dissolved in 10 mL distilled water. The pH value was adjusted to 6.0 with 1 M NaOH. The resulting mixture was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 160 C for 80 h and then slowly cooled to room temperature. Blue block-shaped crystals of 1 were obtained in 69% yield (based on Cu).

Reference： [1]Inorganica Chimica Acta,2020,vol. 502

60
copper(II) choride dihydrate [ No CAS ]
[ 69506-86-1 ]
[ 124-83-4 ]
[ 7732-18-5 ]
4C₁₀H₁₄O₄^(2-)*4Cu⁽²⁺⁾*4C₁₀H₁₄N₄*9H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydroxide; at 160℃; for 80h;pH 6.0;Autoclave;	A mixture of CuCl2·2H2O (85 mg, 0.50 mmol), H2DCA (99 mg, 0.50 mmol) and bimb (96 mg, 0.50 mmol) was dissolved in 10 mL distilled water. The pH value was adjusted to 6.0 with 1 M NaOH. The resulting mixture was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 160 C for 80 h and then slowly cooled to room temperature. Blue block-shaped crystals of 1 were obtained in 69% yield (based on Cu). Elemental analysis (%): Calcd. for (1): C 48.67, H 6.84, N 11.35. Found: C 48.42, H 6.95, N 11.23. IR (KBr): nu (cm-1) = 3415w, 3126w, 2967w, 1637 m, 1616 s, 1557 m, 1456w, 1398 s, 1361w, 1315w, 1288w, 1241w, 1110 m, 953w, 829w, 809w, 760w, 659 m, 629w, 483w.

Reference： [1]Inorganica Chimica Acta,2020,vol. 502

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CAS No. :	124-83-4	MDL No. :	MFCD00001375
Formula :	C₁₀H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LSPHULWDVZXLIL-LDWIPMOCSA-N
M.W :	200.23	Pubchem ID :	101807
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.09
TPSA :	74.6 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.58 cm/s

Log Po/w (iLOGP) :	1.0
Log Po/w (XLOGP3) :	1.33
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	1.03
Consensus Log Po/w :	1.22

[ CAS No. 124-83-4 ] {[proInfo.proName]}

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[ 124-83-4 ] Synthesis Path-Upstream 1~1

[ 124-83-4 ] Synthesis Path-Downstream 1~60

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[ 124-83-4 ]

Carboxylic Acids

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Log S (ESOL) :	-1.79
Solubility :	3.27 mg/ml ; 0.0163 mol/l
Class :	Very soluble
Log S (Ali) :	-2.5
Solubility :	0.636 mg/ml ; 0.00318 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.93
Solubility :	23.6 mg/ml ; 0.118 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.76

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 124-83-4 ] {[proInfo.proName]}

Quality Control of [ 124-83-4 ]

Related Doc. of [ 124-83-4 ]

Product Details of [ 124-83-4 ]

Calculated chemistry of [ 124-83-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 124-83-4 ]

Application In Synthesis of [ 124-83-4 ]

[ 124-83-4 ] Synthesis Path-Upstream 1~1

[ 124-83-4 ] Synthesis Path-Downstream 1~60

Related Functional Groups of [ 124-83-4 ]

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 124-83-4 ]