[ CAS No. 13419-69-7 ]

Name: 13419-69-7|trans-Hex-2-enoic acid|97%
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Quality Control of [ 13419-69-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 13419-69-7 ]

Product Details of [ 13419-69-7 ]

CAS No. :	13419-69-7	MDL No. :	MFCD00002705
Formula :	C₆H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NIONDZDPPYHYKY-SNAWJCMRSA-N
M.W :	114.14	Pubchem ID :	5282707
Synonyms :

Calculated chemistry of [ 13419-69-7 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	32.25
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.59
Log Po/w (WLOGP) :	1.43
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	0.75
Consensus Log Po/w :	1.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.35
Solubility :	5.08 mg/ml ; 0.0445 mol/l
Class :	Very soluble
Log S (Ali) :	-1.98
Solubility :	1.18 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.48
Solubility :	37.5 mg/ml ; 0.329 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 13419-69-7 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 13419-69-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 13419-69-7 ]
Downstream synthetic route of [ 13419-69-7 ]

[ 13419-69-7 ] Synthesis Path-Upstream 1~2

1
[ 6728-26-3 ]
[ 1129294-89-8 ]
[ 98-01-1 ]
[ 496-64-0 ]
[ 88-14-2 ]
[ 13419-69-7 ]
[ 1401094-48-1 ]
[ 1401094-49-2 ]
[ 1309945-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 40, p. 9967 - 9973,7

2
[ 13419-69-7 ]
[ 2396-77-2 ]

Reference： [1] Patent: US4885383, 1989, A,

[ 13419-69-7 ] Synthesis Path-Downstream 1~68

1
[ 141-82-2 ]
[ 123-72-8 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
61.4%	Stage #1: malonic acid; butyraldehyde With 4-methyl-morpholine at 80℃; for 8h; Stage #2: With sulfuric acid In water at 20℃; for 0.5h; regioselective reaction;
	(i) Py, (ii) (decarboxylation); Multistep reaction;
	With pyridine Heating;

Reference： [1]Location in patent: experimental part Zhang, Shi-Jie; Hu, Wei-Xiao [Synthetic Communications, 2010, vol. 40, # 20, p. 3093 - 3100]
[2]Castan,P.; Labarre,J.-F. [Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1966, vol. 262, p. 1301 - 1303]
[3]Han, Sheng Hua; Chen, Jian Xin; Liu, Hong Yan; Zhang, Hai Rong; Ma, Peng Fei [Asian Journal of Chemistry, 2015, vol. 27, # 4, p. 1299 - 1303]

2
[ 67-56-1 ]
[ 13419-69-7 ]
[ 13894-63-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: (E)-2-Hexenoic acid With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: methanol In tetrahydrofuran; N,N-dimethyl-formamide at 10 - 35℃; for 2h;	87 Methyl (2E)-hex-2-enoate Reference Example 87 Methyl (2E)-hex-2-enoate To a solution (100 mL) of (2E)-hex-2-enoic acid (5.0 g) in tetrahydrofuran were added dropwise under ice-cooling oxalyl chloride (3.76 mL) and N,N-dimethylformamide (1 mL). The mixture was stirred at the same temperature for 30 min, methanol (10 mL) was gradually added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was treated with 6% aqueous sodium hydrogencarbonate solution, and extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure (50 Torr, water bath 10°C) to give the title compound as a colorless oil (yield 5.67 g, about 100%). 1H-NMR (CDCl3)δ:0.94 (3H, t, J=7.5 Hz), 1.43-1.53 (2H, m), 2.14-2.21 (2H, m), 3.73 (3H, s), 5.82 (1H, dt, J=1.8, 15.6 Hz), 6.97 (1H, dt, J=6.9, 15.6 Hz).
43%	With ethenetetracarbonitrile at 60℃; for 48h;
	With sulfuric acid Ambient temperature;

With sulfuric acid Reflux;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2336107, 2015, B1 Location in patent: Paragraph 0261
[2]Masaki, Yukio; Tanaka, Nobuyuki; Miura, Tsuyoshi [Chemistry Letters, 1997, # 1, p. 55 - 56]
[3]Alcock, Simon G.; Baldwin, Jack E.; Bohlmann, Rolf; Harwood, Laurence M.; Seeman, Jeffrey I. [Journal of Organic Chemistry, 1985, vol. 50, # 19, p. 3526 - 3535]
[4]Location in patent: experimental part Ballini; Barboni; Castrica; Fringuelli; Lanari; Pizzo; Vaccarob [Advanced Synthesis and Catalysis, 2008, vol. 350, # 9, p. 1218 - 1224]

3
[ 110-44-1 ]
[ 1577-18-0 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In benzene for 48h; Ambient temperature; Yield given. Yields of byproduct given;

Reference： [1]Lee, Jong-Tae; Alper, Howard [Journal of Organic Chemistry, 1990, vol. 55, # 6, p. 1854 - 1856]

4
[ 6728-26-3 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With diphenyl diselenide; dihydrogen peroxide In water at 20℃; for 6h; Green chemistry;	3.2. General Procedure for the Synthesis of Carboxylic Acids 2 General procedure: Diphenyl diselenide (3, 0.006 g; 0.02 mmol) was treated with H2O2 (30%·w/w, 0.1 mL, 1 mmol) andwater (0.2 mL) and stirred at room temperature at 800 rpm until the discoloration of the reaction mixture;then, the aldehyde 1 (1 mmol) was added. After 6 h, the aqueous mixture was extracted three times withEtOAc (3 × 20 mL). The collected organic layers were dried over Na2SO4 and the solvent evaporatedunder reduced pressure.
88%	With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h;
88%	With Iron(III) nitrate nonahydrate; oxygen; sodium 2,2,2-trifluoroacetate In ethyl acetate at 25℃; for 16h;	Typical procedure for the oxidation reaction (Table 1, entry 14). General procedure: In a test tube, trans-2-decenal (167 mg, 1.0 mmol) was added to a suspension of Fe(NO3)3·9H2O(4.1 mg, 0.010 mmol) and CF3COONa (28 mg, 0.20 mmol) in EtOAc (0.50 mL). O2 balloon (1atm) was attached at top of the test tube, and inner atmosphere was replaced by O2. After stirring16 h at 25 °C, EtOAc (3 mL) and 1M HCl aq. (1 mL) were added and resulting biphasic mixture wasstirred for 1 min. Organic phase was separated, and water phase was extracted by EtOAc (3 mL X2). To the collected organic phase was then added measured amount of biphenyl (as an internalstandard for NMR analysis). The conversion of substrate and the yield of products weredetermined by NMR analysis (400 MHz, CDCl3, 25 °C). Products were identified by comparison tothe NMR signals of authentic samples. The same reaction was performed twice for each reaction.

87%	With iron oxide; oxygen; ethyl acetoacetate at 75 - 80℃; for 24h; Green chemistry;	Typical procedure for the oxidation of aldehydes to carboxylic acids General procedure: To a vial with the catalyst (20 mol %) under air, aldehyde (0.0625 mmol) and ethyl acetoacetate (1 equiv) were added. The mixture was heated at 75-80 °C for 24 h. After cooling at rt, ethyl acetate (1.0 ml) was added and the catalyst was separated by simple magnetic decantation. Then, the combined solvent was removed in vacuo and the mixture was purified via trituration or flash column. Spectroscopic data of products 2 were consistent with those reported in the literature (2a,14 2b,15 2c,16 2d,14 2e,17 2f,14 2h,18 2i,19 2j20 and 2k21). trans-Hex-2-enoic acid (2j): ;6.2 mg, 87% yield. 1H NMR (400 MHz, CDCl3) δ 7.06 (dt, 1H, J = 15.6, 6.8 Hz), 5.83 (d, 1H, J = 15.6 Hz), 2.25-2.19 (m, 2H), 1.54-1.46 (m, 2H), 0.95 (t, 3H, J = 7.6 Hz). 13C NMR (100 MHz, CDCl3) δ 171.5, 152.4, 120.5, 34.3, 21.1, 13.6.
71 %Chromat.	Stage #1: (E)-2-Hexenal With palladium(II) trifluoroacetate at 10℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 10℃; chemoselective reaction;
	With tert.-butylhydroperoxide In water; acetonitrile at 60℃; for 5h;
	With Arabidopsis thaliana aldehyde dehydrogenase 3H₁; NAD aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Sancineto, Luca; Tidei, Caterina; Bagnoli, Luana; Marini, Francesca; Lenardo, Eder J.; Santi, Claudio [Molecules, 2015, vol. 20, # 6, p. 10496 - 10510]
[2]Dalcanale, Enrico; Montanari, Fernando [Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 567 - 569]
[3]Tanaka, Shinji; Kon, Yoshihiro; Uesaka, Yumiko; Morioka, Ryo; Tamura, Masanori; Sato, Kazuhiko [Chemistry Letters, 2016, vol. 45, # 2, p. 188 - 190]
[4]Villano, Rosaria; Acocella, Maria Rosaria; Scettri, Arrigo [Tetrahedron Letters, 2014, vol. 55, # 15, p. 2442 - 2445]
[5]Kon, Yoshihiro; Imao, Daisuke; Nakashima, Takuya; Sato, Kazuhiko [Chemistry Letters, 2009, vol. 38, # 5, p. 430 - 431]
[6]Location in patent: experimental part Chattopadhyay, Tanmay; Kogiso, Masaki; Asakawa, Masumi; Shimizu, Toshimi; Aoyagi, Masaru [Catalysis Communications, 2010, vol. 12, # 1, p. 9 - 13]
[7]Location in patent: experimental part Stiti, Naim; Adewale, Isaac O.; Petersen, Jan; Bartels, Dorothea; Kirch, Hans-Hubert [Biochemical Journal, 2011, vol. 434, # 3, p. 459 - 471]

5
[ 64-17-5 ]
[ 13419-69-7 ]
[ 27829-72-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3941 - 3944

6
[ 13419-69-7 ]
[ 97943-16-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
97%	With thionyl chloride; N,N-dimethyl-formamide for 0.666667h; Reflux; Inert atmosphere;
90%	With oxalyl dichloride In diethyl ether for 14h; Ambient temperature;

74%	With thionyl chloride Reflux; Inert atmosphere;
64%	With thionyl chloride for 15h; Heating;
63%	With thionyl chloride In N,N-dimethyl-formamide for 1.5h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 0.5h; Ambient temperature;
32.5 g	With oxalyl dichloride In benzene at 65℃; for 2h;
	With oxalyl dichloride In diethyl ether
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
	With oxalyl dichloride In dichloromethane at 20℃; for 5h;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2.25h;	4.2. Typical procedure for the preparation of N-trityl-3-alkenamides from α,β-unsaturated acids General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 °C. The mixture was allowed to stir for 15 min at 0 °C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 °C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 °C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5% potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90%.
	With oxalyl dichloride at 80℃; for 1h;
	With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Schlenk technique;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.166667h;	4.21. General procedure for the preparation of compounds 8a-g, 9a-g, 10a-e and 11a-e General procedure: Oxalyl chloride (2.0 mmol) was added drop-wise to a stirred mixture of the corresponding acrylic acid derivatives (Acrylic acid, Methacrylic acid, 3,3-Dimethacrylic acid, Trans-2-butenoic acid, Trans-2-pentenoic acid, 4-methyl-2-pentenoic acid, Trans-2-hexenoic acid) (1.0 mmol) and DMF (0.02 mmol) in dichloromethane (16 mL) at room temperature for 10 min, and the mixture was distilled and dissolved in dichloromethane (16 mL) immediately. The solution was used for the next step without further purification. Then, the solution was added drop-wise to a solution of compounds 6a-d (0.4 mmol) and diisopropylethylamine (0.4 mmol) in dichloromethane (15 mL) in an ice bath. Upon completion of the addition, the reaction mixture was removed from the ice bath and placed at room temperature for 30 min and monitored by TLC. The mixture was washed with 10% K2CO3 (50 mL * 3) followed by saturated aqueous NaCl (50 mL * 1), and the organic phase was separated, dried, and evaporated to yield 8a-g, 9a-g, 10a-e and 11a-e which were purified by dichloromethane.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; Inert atmosphere;

Reference： [1]Lee, Yong Ho; Denton, Elliott H.; Morandi, Bill [Journal of the American Chemical Society, 2020, vol. 142, # 50, p. 20948 - 20955]
[2]Sib, Anna; Gulder, Tobias A. M. [Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 12888 - 12891][Angew. Chem., 2017, vol. 129, # 42, p. 13068 - 13071,4]
[3]Oppolzer, Wolfgang; Barras, Jean-Pierre [Helvetica Chimica Acta, 1987, vol. 70, p. 1666 - 1675]
[4]Wickel, Susanne M.; Citron, Christian A.; Dickschat, Jeroen S. [European Journal of Organic Chemistry, 2013, # 14, p. 2906 - 2913]
[5]Iwai; Kohda; Fukaya; Naito; Yokoyama; Nakajima; Tsujikawa; Okabe; Mimura [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 11, p. 4616 - 4625]
[6]Lauk, Urs H.; Skrabal, Peter; Zollinger, Heinrich [Helvetica Chimica Acta, 1985, vol. 68, p. 1406 - 1426]
[7]Penn, John H.; Liu, Fang [Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2608 - 2612]
[8]Leal; Higuchi; Mizutani; Nakamori; Kadosawa; Ono [Journal of Chemical Ecology, 1995, vol. 21, # 7, p. 973 - 985]
[9]Shintani, Ryo; Kimura, Takahiro; Hayashi, Tamio [Chemical Communications, 2005, # 25, p. 3213 - 3214]
[10]Sibi, Mukund P.; Itoh, Kennosuke [Journal of the American Chemical Society, 2007, vol. 129, # 26, p. 8064 - 8065]
[11]Chuang, Ta-Hsien; Chen, Yu-Chi; Pola, Someshwar [Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6625 - 6630]
[12]Location in patent: experimental part Theodorou, Vassiliki; Gogou, Marina; Philippidou, Maria; Ragoussis, Valentine; Paraskevopoulos, Georgios; Skobridis, Konstantinos [Tetrahedron, 2011, vol. 67, # 31, p. 5630 - 5634]
[13]Cowie, Thomas Y.; Veguillas, Marcos; Rae, Robert L.; Rougé, Mathilde; Zurek, Justyna M.; Prentice, Andrew W.; Paterson, Martin J.; Bebbington, Magnus W. P. [Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6656 - 6670]
[14]Rodríguez-Fernández, Mamen; Yan, Xingchen; Collados, Juan F.; White, Paul B.; Harutyunyan, Syuzanna R. [Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14224 - 14231]
[15]OuYang, Yiqiang; Zou, Wensheng; Peng, Liang; Yang, Zunhua; Tang, Qidong; Chen, Mengzi; Jia, Shuang; Zhang, Hong; Lan, Zhou; Zheng, Pengwu; Zhu, Wufu [European Journal of Medicinal Chemistry, 2018, vol. 154, p. 29 - 43]
[16]Zhang, Lei; Bao, Wangzhen; Liang, Yuchen; Pan, Wenjing; Li, Dongyang; Kong, Lichun; Wang, Zhi-Xiang; Peng, Bo [Angewandte Chemie - International Edition, 2021, vol. 60, # 20, p. 11414 - 11422][Angew. Chem., 2021, vol. 133, # 20, p. 11515 - 11523,9]

7
[ 13419-69-7 ]
[ 96096-69-4 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With cetylpyridinium chloride; dihydrogen peroxide; sodium hydroxide In water at 20 - 50℃; for 5.5h;	3 Example 1 Example 3. To a 1L reaction flask, 400g water was added and trans-2-hexenoic acid (45.7g, 0.4mol) and cetyl pyridinium chloride (20.4g, 0.06mol) were added under stirring. The pH of the mixture was adjusted to about 6 with 30% sodium hydroxide solution and then 30% hydrogen peroxide (102.3g, 0.9mol) was added into the mixture. Afterwards, the reaction mixture was heated to 50°C and was allowed to further react for 5.5 hours until completion of the reaction. The reaction mixture was cooled to room temperature and the pH was adjusted to about 2 with concentrated hydrochloric acid. The mixture was extracted twice with 400g dichloromethane. The extract was concentrated until dryness. 49.4g product was obtained with a yield of 93.5%.
	With potassium hydroxide; sodium tungstate; dihydrogen peroxide In water at 60 - 65℃; for 2h; Yield given;
	With potassium hydroxide; sulfuric acid; dihydrogen peroxide In water at 60 - 65℃; for 8h; pH=6-7; Yield given;

With Oxone; edetate disodium; sodium hydrogencarbonate In water; acetone for 4h;

1 Example 1 - Synthesis of 3-propyloxirane-2-carboxylic acid (VI) Trans-2-hexenoic acid (70 g, 0.61 mol) is dissolved in a mixture of acetone (140 mL) and water (140 mL). Solid NaHCO3 (205 g, 2.44 mol) is added to this mixture under stirring in portions. A mixture consisting of oxone (395 g, 1.29 mol), Na2EDTA dihydrate (0.18 g) and water (1.4 L ) is added in 2 hours. After a further 2 hours the reaction mixture is cooled to 0°C and treated slowly with a 37% HC1 solution to pH 2. The reaction mixture is then extracted with ethyl acetate and the combined organic phases are washed with water and a saturated solution of NaCl. The organic phase is dried on sodium sulphate, filtered and concentrated at low pressure until 3-propyloxirane-2-carboxylic acid (VI) is obtained with a yield of 93%; it is not purified, but used "as is" for the subsequent reactions. 1H-NMR, (CDC13) δ: 3.25 (d, 1H, J = 1.2 Hz), 3.19 (dt, 1H, J = 1.2, 6.9 Hz), 1.71-1.41 (m, 4H), 0.98 (t, 3H, J = 7.8 Hz)

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHEJIANG XINHUA PHARMACEUTICAL - WO2013/186248, 2013, A1 Location in patent: Page/Page column 19-20
[2]Kirschenbaum, Kenneth S.; Sharpless, K. Barry [Journal of Organic Chemistry, 1985, vol. 50, # 11, p. 1979 - 1982]
[3]Oguchi, Takahito; Sakata, Yasuyuki; Takeuchi, Naotoshi; Kaneda, Kimio; Ishii, Yasutaka; Ogawa, Masaya [Chemistry Letters, 1989, p. 2053 - 2056]
[4]Current Patent Assignee: DIPHARMA FRANCIS S.R.L. - WO2013/136265, 2013, A1 Location in patent: Page/Page column 19

8
[ 13419-69-7 ]
[ 74-88-4 ]
[ 13894-63-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With cesium fluoride In N,N-dimethyl-formamide at 10 - 15℃; for 24h;

Reference： [1]Sato, Tsuneo; Otera, Junzo; Nozaki, Hitosi [Journal of Organic Chemistry, 1992, vol. 57, # 7, p. 2166 - 2169]

9
[ 13419-69-7 ]
(E)-2-hexenoyl azide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diphenylphosphoranyl azide
	With diphenyl-phosphinic acid
	With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 16h; Inert atmosphere;

Reference： [1]Zhou, Aihua; Cao, Liwei; Li, Haiqing; Liu, Zhuqing; Pittman Jr., Charles U. [Synlett, 2006, # 2, p. 201 - 206]
[2]Snider; Song [Organic letters, 2000, vol. 2, # 3, p. 407 - 408]
[3]Gelis, Coralie; Bekkaye, Mathieu; Lebée, Clément; Blanchard, Florent; Masson, Géraldine [Organic Letters, 2016, vol. 18, # 14, p. 3422 - 3425]

10
[ 13419-69-7 ]
[ 133524-70-6 ]
3'-N-(trans-2-hexenoyl)-3'-N-debenzoylpaclitaxel [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;

Reference： [1]Skwarczynski, Mariusz; Sohma, Youhei; Noguchi, Mayo; Kimura, Maiko; Hayashi, Yoshio; Hamada, Yoshio; Kimura, Tooru; Kiso, Yoshiaki [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2655 - 2666]

11
[ 13419-69-7 ]
[ 75-08-1 ]
[ 862463-96-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;

Reference： [1]Des Mazery, Renaud; Pullez, Maddalena; Lopez, Fernando; Harutyunyan, Syuzanna R.; Minnaard, Adriaan J.; Feringa, Ben L. [Journal of the American Chemical Society, 2005, vol. 127, # 28, p. 9966 - 9967]

12
[ 3095-95-2 ]
[ 123-72-8 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethylphosphonoacetic acid With sodium hydride In 1,2-dimethoxyethane at 20℃; Stage #2: butyraldehyde In 1,2-dimethoxyethane at 20℃; Further stages.;

Reference： [1]Sibi, Mukund P.; Itoh, Kennosuke [Journal of the American Chemical Society, 2007, vol. 129, # 26, p. 8064 - 8065]

13
2-benzyloxy-1-methylpyridinium triflate [ No CAS ]
[ 13419-69-7 ]
[ 131375-80-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine In various solvent(s) at 83℃; for 24h;

Reference： [1]Tummatorn, Jumreang; Albiniak, Philip A.; Dudley, Gregory B. [Journal of Organic Chemistry, 2007, vol. 72, # 23, p. 8962 - 8964]

14
[ 934-60-1 ]
[ 7340-22-9 ]
[ 93-10-7 ]
C₂₅H₃₂N₃O₆Pol [ No CAS ]
[ 13419-69-7 ]
[ 5537-71-3 ]
[ 65-85-0 ]
C₃₂H₃₆N₃O₇Pol [ No CAS ]
C₃₃H₃₇N₄O₇Pol [ No CAS ]
C₃₁H₄₀N₃O₇Pol [ No CAS ]
C₃₂H₃₇N₄O₇Pol [ No CAS ]
C₃₅H₃₇N₄O₇Pol [ No CAS ]
C₃₅H₃₉N₄O₇Pol [ No CAS ]

Reference： [1]Patent: US2005/215553,2005,A1 .Location in patent: Page/Page column 9

15
[ 7774-74-5 ]
[ 13419-69-7 ]
3-(2-Thienylthio)hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran	1.A Step A Step A Preparation of 3-(2-Thienylthio)hexanoic acid (2) A solution of 2-mercaptothiophene (51.1 g, 0.44 mol), trans-2-hexenoic acid (1) (49.1 g, 0.43 mol), triethylamine (29.3 g, 0.29 mol) in tetrahydrofuran (490 ml) was stirred and refluxed under nitrogen for 21 hours. The mixture was concentrated in vacuo and the residue was distributed between ethyl acetate (500 ml) and 3N hydrochloric acid (200 ml), the aqueous layer was separated and extracted with ethyl acetate (200 ml), the combined ethyl acetate extracts were washed with 3N hydrochloric acid, twice with water and dried over sodium sulfate. The solvent was evaporated in vacuo to yield pale yellow oily product weighing 99 g (100%), which was >96% pure by HPLC.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5091409, 1992, A

16
[ 123-72-8 ]
[ 27829-72-7 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; malonic acid; sulfuric acid; In diethyl ether;	(1) Ethyl 2-trans-n-hexenoate A mixture of 176 g. of malonic acid, 176 ml. of pyridine and 108 ml. of butanal was stirred at room temperature for 22 hours, at 40° to 45°C. for 20 hours and at 60° to 65°C. for 3 hours, successively. The reaction mixture was acidified with 250 ml. of 6N sulphuric acid. Diethyl ether was added and the aqueous layer separated. The aqueous layer was extracted with diethyl ether, and the combined organic layers were washed with 6N sulphuric acid, dried over calcium chloride and concentrated under reduced pressure to give 112 g. of 2-trans-n-hexenoic acid having the following physical characteristic: NMR (CDCl3 solution); delta: 12.4 (1H, s), 7.5-6.9 (1H, m), 6.2-5.7 (1H, d), 2.5-2.0 (2H, q), 1.85-1.2 (2H, m) and 0.95 (3H, t).

Reference： [1]Patent: US3978229,1976,A

17
[ 13419-69-7 ]
[ 27829-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In diethyl ether; ethanol; benzene;	2-trans-n-Hexenoic acid (112 g.) was dissolved in a mixture of 400 ml. of benzene and 117 ml. of ethanol, 11.2 g. of p-toluenesulphonic acid were added an the mixture was refluxed overnight. The reaction mixture was diluted with 600 ml. of diethyl ether, washed and saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and concentrated under reduced pressure. Distillation of the crude product gave 105 g. of ethyl 2-trans-n-hexenoate having the following physical characteristics: b.p. 71°-72°C./20 mm.Hg; NMR (CDCl3 solution); delta: 7.2-6.65 (1H, m), 6.0-5.5 (1H, d); 4.4-3.9 (2H, q) and 2.4-1.9 (2H, q).

Reference： [1]Patent: US3978229,1976,A

18
concentrated H₂ SO₄ [ No CAS ]
[ 13419-69-7 ]
[ 2396-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol;	EXAMPLE 5 Preparation of 2-Hexenoic Acid Methyl Ester The reaction is performed and the catalyst separated in the manner described in Example 1. Acid feed: 342.6 g 2-hexenoic acid (3.0 mols) Catalyst: 3.0 g concentrated H2 SO4 Test duration: 6 hours Methanol added: 64.0 g/hr. (2.0 mols) Bottom temperature: 125 C. Head temperature: 67-85 C. Amount of distillate: 386.0 g Residue: 340.0 g (catalyst-free)

Reference： [1]Patent: US4885383,1989,A

19
[ 79-37-8 ]
[ 13419-69-7 ]
[ 144-55-8 ]
[ 13894-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; N,N-dimethyl-formamide	R.87 Methyl (2E)-hex-2-enoate Reference Example 87 Methyl (2E)-hex-2-enoate To a solution (100 mL) of (2E)-hex-2-enoic acid (5.0 g) in tetrahydrofuran were added dropwise under ice-cooling oxalyl chloride (3.76 mL) and N,N-dimethylformamide (1 mL). The mixture was stirred at the same temperature for 30 min, methanol (10 mL) was gradually added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was treated with 6% aqueous sodium hydrogencarbonate solution, and extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure (50 Torr, water bath 10°C) to give the title compound as a colorless oil (yield 5.67 g, about 100%). 1H-NMR (CDCl3)δ:0.94 (3H, t, J=7.5 Hz), 1.43-1.53 (2H, m), 2.14-2.21 (2H, m), 3.73 (3H, s), 5.82 (1H, dt, J=1.8, 15.6 Hz), 6.97 (1H, dt, J=6.9, 15.6 Hz).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1803709, 2007, A1

20
[ 13419-69-7 ]
[ 13033-84-6 ]
[ 1012338-69-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;

Reference： [1]Kopp, Florian; Linne, Uwe; Oberthuer, Markus; Marahiel, Mohamed A. [Journal of the American Chemical Society, 2008, vol. 130, # 8, p. 2656 - 2666]

21
[ 13419-69-7 ]
[ 275815-80-0 ]
[ 1058645-24-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Santella III, Joseph B.; Gardner, Daniel S.; Yao, Wenqing; Shi, Chongsheng; Reddy, Prabhakar; Tebben, Andrew J.; DeLucca, George V.; Wacker, Dean A.; Watson, Paul S.; Welch, Patricia K.; Wadman, Eric A.; Davies, Paul; Solomon, Kimberly A.; Graden, Dani M.; Yeleswaram, Swamy; Mandlekar, Sandhya; Kariv, Ilona; Decicco, Carl P.; Ko, Soo S.; Carter, Percy H.; Duncia, John V. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 576 - 585]

22
[ 1020737-07-8 ]
[ 13419-69-7 ]
[ 1020737-71-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;

Reference： [1]Neisius, N. Matthias; Plietker, Bernd [Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3218 - 3227]

23
[ 13419-69-7 ]
[ 94594-90-8 ]
[ 114951-07-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;

Reference： [1]Neisius, N. Matthias; Plietker, Bernd [Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3218 - 3227]

24
[ 13419-69-7 ]
[ 765-30-0 ]
[ 950986-78-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; <i>tert</i>-butyl alcohol In dichloromethane at 20℃;	1 Intermediate IX mentioned above was prepared by the method illustrated in Scheme 5 below: N-methyl morphorline (6.0 mL) was added to a solution of hex-2-enoic acid (11.4 g, 0.1 mol), EDC (29.6 g, 0.15 mol), ButOH (13.5 g, 0.1 mol) and cyclopropylamine (5.7 g, 0.1 mol) in CH2Cl2 (300 mL) at room temperature. After the reaction mixture was stirred at the same temperature overnight, it was quenched with water. The mixture was then extracted with CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, concentrated, and purified by silica gel chromatography to afford 12.2 g (yield: 80%) of intermediate IXa.

Reference： [1]Current Patent Assignee: TAIGEN BIOPHARMACEUTICALS HOLDINGS LTD. - US2008/108632, 2008, A1 Location in patent: Page/Page column 18

25
[ 13419-69-7 ]
[ 75-16-1 ]
[ 116169-10-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: (E)-2-Hexenoic acid; methylmagnesium bromide With copper(l) iodide; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] In diethyl ether; dichloromethane; tert-butyl methyl ether at -20℃; Stage #2: With ammonium chloride In methanol; water enantioselective reaction;

Reference： [1]Lum, Tze-Keong; Wang, Shun-Yi; Loh, Teck-Peng [Organic Letters, 2008, vol. 10, # 5, p. 761 - 764]

26
[ 13419-69-7 ]
cyclo[L-Val⁽¹⁾-Z-Dhb-L-Phe-D-Val⁽²⁾-D-allo-Ile⁽¹⁾-D-allo-Thr⁽¹⁾]-D-allo-Ile⁽²⁾-L-Orn-D-Pro-D-Val⁽³⁾-L-Val⁽⁴⁾-L-Thr⁽²⁾-D-Val⁽⁵⁾-5-MeHex [ No CAS ]
[ 1050505-68-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 23℃; for 2h;

Reference： [1]Jiménez, José C.; López-Macià, Angel; Gracia, Carol; Varón, Sonia; Carrascal, Marta; Caba, Josep M.; Royo, Miriam; Francesch, Andrés M.; Cuevas, Carmen; Giralt, Ernest; Albericio, Fernando [Journal of Medicinal Chemistry, 2008, vol. 51, # 16, p. 4920 - 4931]

27
[ 13419-69-7 ]
[ 928-49-4 ]
[ 1264639-81-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With Pd2(p-tolyl)2(μ-OH)(μ-N,N'-bis[2-(diphenylphosphino)phenyl]formamidinate); tributyl borane In tetrahydrofuran at 100℃; for 17h; Inert atmosphere; Combinatorial reaction / High throughput screening (HTS); stereoselective reaction;	General procedure for the reaction of alkynes and carboxylic acids. General procedure: To a mixture of 1 (0.01 mmol) and a carboxylic acid (5.00 mmol) were added an alkyne (0.50 mmol), and then a 1 M THF solution of tri-n-butylborane (0.15 ml, 0.15 mmol) in a pressure vial. After heating at 100 °C for 17 h, the mixture was cooled to room temperature and filtered through a short plug of silica gel using ether or dichloromethane as an eluent. Volatiles were evaporated and the residue was purified by silica gel column chromatography to give alkenyl esters.

Reference： [1]Tsukada, Naofumi; Takahashi, Atsushi; Inoue, Yoshio [Tetrahedron Letters, 2011, vol. 52, # 2, p. 248 - 250]

28
[ 13419-69-7 ]
[ 5824-40-8 ]
N-trityl-3-hexenamide [ No CAS ]
N-trityl-2-hexenamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 0 - 20℃;	4.4. Typical procedure for the preparation of N-tritylamides from α,β-unsaturated acids with PyBroP as coupling reagent General procedure: To a solution of the carboxylic acid (1 mmol) in dry DCM (3 mL), TrNH2 (1 mmol), PyBroP (1 mmol) and Et3N (3 mmol) in DCM (2 mL) were added and the mixture was allowed to stir at 0 °C for 5 min and at rt overnight, until completion of the reaction. The mixture was then diluted with AcOEt (25 mL), washed with water, 5% KHSO4, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel. The obtained N-tritylamides were mixtures of α,β- and β,γ-unsaturated compounds, as identified by 1H NMR spectroscopy.

Reference： [1]Location in patent: experimental part Theodorou, Vassiliki; Gogou, Marina; Philippidou, Maria; Ragoussis, Valentine; Paraskevopoulos, Georgios; Skobridis, Konstantinos [Tetrahedron, 2011, vol. 67, # 31, p. 5630 - 5634]

29
[ 13419-69-7 ]
[ 62-53-3 ]
[ 859189-41-6 ]
[ 1483-36-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 0 - 20℃;	4.4. Typical procedure for the preparation of N-tritylamides from α,β-unsaturated acids with PyBroP as coupling reagent General procedure: To a solution of the carboxylic acid (1 mmol) in dry DCM (3 mL), TrNH2 (1 mmol), PyBroP (1 mmol) and Et3N (3 mmol) in DCM (2 mL) were added and the mixture was allowed to stir at 0 °C for 5 min and at rt overnight, until completion of the reaction. The mixture was then diluted with AcOEt (25 mL), washed with water, 5% KHSO4, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel. The obtained N-tritylamides were mixtures of α,β- and β,γ-unsaturated compounds, as identified by 1H NMR spectroscopy.

30
[ 477532-70-0 ]
[ 13419-69-7 ]
[ 1359767-65-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;	4.7.15. Methyl (S)-2-[(2E,4E)-5-methylhexadienoyl]-7-(2-{5-methyl-2-[(1E)-5-methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (15a) General procedure: To a solution of 12i (700 mg, 1.70 mmol) in CH2Cl2 (7 ml) was added (2E,4E)-5-methylhexadienoic acid (180 mg, 2.22 mmol) and EDC (490 mg, 2.56 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 h. The reaction mixture was washed with water and saturated brine and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 15a (700 mg, 79% yield) as an oil.

Reference： [1]Location in patent: experimental part Otake, Kazuya; Azukizawa, Satoru; Fukui, Masaki; Kunishiro, Kazuyoshi; Kamemoto, Hikaru; Kanda, Mamoru; Miike, Tomohiro; Kasai, Masayasu; Shirahase, Hiroaki [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 1060 - 1075]

31
[ 13419-69-7 ]
N-(2-methyl-4-pyridyl)propane-1,3-diamine hydrochloride [ No CAS ]
[ 1370538-03-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: (E)-2-Hexenoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide; acetonitrile for 0.0833333h; Stage #2: N-(2-methyl-4-pyridyl)propane-1,3-diamine hydrochloride With triethylamine In N,N-dimethyl-formamide; acetonitrile for 1h;	5.B Step B: (E)-N-[3-[(2-Methyl-4-pyridyl)amino]propyl]hex-2-enamide; (£)-4-Hex-2-enoic acid (23 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1 : 1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 5 minutes triethylamine (82 μΙ, 0.6 mmol) and N-(2-Methyl-4-pyridyl)propane-1 ,3-diamine hydrochloride (40 mg, 0.2 mmol) was added. To the mixture basic aluminium oxide was added, stirring was continued for one hour, the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1 % NH3 and acetonitrile) to yield 20.2 mg (0.077 mmol, 39 %).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2012/41873, 2012, A1 Location in patent: Page/Page column 90

32
[ 13419-69-7 ]
[ 1190-73-4 ]
(E)-S-(hex-2-enoyl)-N-acetylcysteamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: (E)-2-Hexenoic acid In dichloromethane at 0℃; for 0.25h; Stage #2: 2-(acetylamino)ethanethiol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃;
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;
64.5 mg	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	Synthesis of acyl-NAC substrates General procedure: Crotonic acid (103 mg) was dissolved in CH2Cl2 (5 ml) at 0 °C and stirred for 15 min. A solution of N,N'-dicyclohexylcarbodiimide (274 mg) and 4-(dimethylamino)pyridine (13.7 mg) in CH2Cl2 (5 ml) and NAC (150 mg) were added to the crotonic acid solution simultaneously with two syringes. The mixture was then stirred for 2 days at room temperature. After the slurry was filtered off, the solvent was evaporated. The residue was then purified by silica gel column chromatography (hexane:ethyl acetate = 1:2) to provide crotonoyl-NAC (147 mg).

Reference： [1]Location in patent: experimental part Jensen, Katja; Niederkrueger, Holger; Zimmermann, Katrin; Vagstad, Anna L.; Moldenhauer, Jana; Brendel, Nicole; Frank, Sarah; Poeplau, Petra; Kohlhaas, Christoph; Townsend, Craig A.; Oldiges, Marco; Hertweck, Christian; Piel, Joern [Chemistry and Biology, 2012, vol. 19, # 3, p. 329 - 339]
[2]Singh, Renu; Reynolds, Kevin A. [ChemBioChem, 2015, vol. 16, # 4, p. 631 - 640]
[3]Chisuga, Taichi; Miyanaga, Akimasa; Kudo, Fumitaka; Eguchi, Tadashi [Journal of Biological Chemistry, 2017, vol. 292, # 26, p. 10926 - 10937]

33
[ 6728-26-3 ]
[ 1129294-89-8 ]
[ 98-01-1 ]
[ 496-64-0 ]
[ 88-14-2 ]
[ 13419-69-7 ]
[ 1401094-48-1 ]
[ 1401094-49-2 ]
[ 1309945-34-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 9967 - 9973,7

34
[ 13419-69-7 ]
[ 1415113-42-6 ]
(E)-N'-hex-2-enoyl-N-2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetohydrazid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.6%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 12h;

Reference： [1]Zhang, Shi-Jie; Ding, Zhi-Shan; Jiang, Fu-Sheng; Ge, Qiu-Fu; Guo, Dian-Wu; Li, Hai-Bo; Hu, Wei-Xiao [MedChemComm, 2014, vol. 5, # 4, p. 512 - 520]

35
[ 928-94-9 ]
[ 13419-69-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: (Z)-2-hexen-1-ol With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; oxygen; copper(I) bromide In acetonitrile at 20℃; for 16h; Schlenk technique; Stage #2: With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 0 - 20℃; for 12.25h;

Reference： [1]Könning, Daniel; Olbrisch, Tobias; Sypaseuth, Fanni D.; Tzschucke, C. Christoph; Christmann, Mathias [Chemical Communications, 2014, vol. 50, # 39, p. 5014 - 5016]

36
[ 13419-69-7 ]
[ 168297-85-6 ]
[ 1647060-92-1 ]