[ CAS No. 464-78-8 ] {[proInfo.proName]}

Name: 464-78-8|7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid|98%
Brand: Ambeed
SKU: A403073
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Quality Control of [ 464-78-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 464-78-8 ]

SDS Specification

Alternatived Products of [ 464-78-8 ]

Product Details of [ 464-78-8 ]

CAS No. :	464-78-8	MDL No. :	MFCD00168053
Formula :	C₁₀H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WDODWBQJVMBHCO-UHFFFAOYSA-N
M.W :	182.22	Pubchem ID :	297888
Synonyms :

Calculated chemistry of [ 464-78-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.41
TPSA :	54.37 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) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.13
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	1.47
Log Po/w (MLOGP) :	1.2
Log Po/w (SILICOS-IT) :	1.76
Consensus Log Po/w :	1.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-2.14
Solubility :	1.31 mg/ml ; 0.00716 mol/l
Class :	Soluble
Log S (Ali) :	-2.74
Solubility :	0.334 mg/ml ; 0.00183 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.6
Solubility :	4.55 mg/ml ; 0.0249 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.22

Safety of [ 464-78-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 464-78-8 ]

* 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.

Downstream synthetic route of [ 464-78-8 ]

[ 464-78-8 ] Synthesis Path-Downstream 1~52

1
[ 464-78-8 ]
[ 937-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol
	With sodium hydroxide; hydrazine In ethylene glycol at 210℃;
	With potassium hydroxide; hydrazine hydrate In diethylene glycol at 205℃;

Reference： [1]Kursanow; Witt [Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2509,2511;engl.Ausg.S.2401]
[2]Deno,N.C. et al. [Journal of the American Chemical Society, 1960, vol. 82, p. 4719 - 4723]
[3]Bunce,N.J.; Murray,N.G. [Tetrahedron, 1971, vol. 27, p. 5323 - 5335]

2
[ 464-78-8 ]
[ 6053-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate
	With nitric acid
	With nitric acid

Reference： [1]Gilles; Renwick [p. 182][Chemisches Zentralblatt, 1897, vol. 68, # II, p. 550]
[2]Gilles; Renwick [p. 182][Chemisches Zentralblatt, 1897, vol. 68, # II, p. 550]
[3]Bredt; May [Chemiker-Zeitung, Chemische Apparatur, 1910, vol. 34, p. 65]

3
Campher-10-chlorsulfoxid [ No CAS ]
[ 464-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; sodium carbonate In acetone

Reference： [1]Bunce,N.J.; Murray,N.G. [Tetrahedron, 1971, vol. 27, p. 5323 - 5335]

4
[ 464-78-8 ]
[ 19493-09-5 ]
[ 125554-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen Yield given. Multistep reaction;

Reference： [1]Ishizuka, Tadao; Ishibuchi, Seigo; Kunieda, Takehisa [Tetrahedron Letters, 1989, vol. 30, # 26, p. 3449 - 3452]

5
[ 464-78-8 ]
[ 34252-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	(i) HgO, MgSO₄, (ii) Br₂; Multistep reaction;
93.6 mg	With iodobenzene difluoride; potassium bromide In dichloromethane at 25℃; Irradiation;

Reference： [1]Brown,R.F.C. et al. [Australian Journal of Chemistry, 1978, vol. 31, p. 2727 - 2735]
[2]Kanazawa, Junichiro; Koyamada, Kenta; Miyamoto, Kazunori; Uchiyama, Masanobu; Watanabe, Ayumi [Organic process research and development, 2020, vol. 24, # 7, p. 1328 - 1334]

Yield	Reaction Conditions	Operation in experiment
	With water d-ketopinoic acid;
	With water; calcium carbonate at 180℃; im Rohr; d-ketopinoic acid;
	With calcium hydroxide; water at 180℃; im Rohr; d-ketopinoic acid;

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 20℃;

8
[ 617-89-0 ]
[ 7188-38-7 ]
[ 464-78-8 ]
3-furan-2-ylmethyl-9,9-dimethyl-2-oxo-3-aza-tricyclo[4.2.1.0^1,4]nonane-4-carboxylic acid <i>tert</i>-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With D-glucose at 25℃; for 144h;

Reference： [1]Pirrung, Michael C.; Das Sarma, Koushik [Synlett, 2004, # 8, p. 1425 - 1427]

9
[ 7188-38-7 ]
[ 20781-20-8 ]
[ 464-78-8 ]
3-(2,4-dimethoxy-benzyl)-9,9-dimethyl-2-oxo-3-aza-tricyclo[4.2.1.0^1,4]nonane-4-carboxylic acid <i>tert</i>-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With D-glucose at 25℃; for 144h;

Reference： [1]Pirrung, Michael C.; Das Sarma, Koushik [Synlett, 2004, # 8, p. 1425 - 1427]

10
[ 50-00-0 ]
[ 464-78-8 ]
(1S,4S)-7,7-Dimethyl-3-methylene-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: formaldehyd; ketopinic acid With acetic acid Stage #2: With Diethyl amine at 100℃;

Reference： [1]Reddy, N. Laxma; Hill, Jeanette; Ye, Long; Fernandes, Prabhavathi B.; Stout, David M. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5645 - 5649]

11
[ 464-78-8 ]
[ 54371-12-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride
	With dmap; thionyl chloride In dichloromethane
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane

Reference： [1]Reddy, N. Laxma; Hill, Jeanette; Ye, Long; Fernandes, Prabhavathi B.; Stout, David M. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5645 - 5649]
[2]Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Scialpi, Rosanna; Spagnolo, Piero; Zanardi, Giuseppe [Synlett, 2004, # 6, p. 985 - 990]
[3]Na, Christina G.; Ravelli, Davide; Alexanian, Erik J. [Journal of the American Chemical Society, 2020, vol. 142, # 1, p. 44 - 49]

12
[ 464-78-8 ]
[ 38989-01-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diphenylphosphoranyl azide; triethylamine In toluene for 0.5h; Heating;

Reference： [1]Spino, Claude; Joly, Marc-Andre; Godbout, Cedrickx; Arbour, Melissa [Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6118 - 6121]

13
[ 464-78-8 ]
[ 150-76-5 ]
4-methoxyphenyl 7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With TiO(acac)2 In xylene for 36h; Heating;

Reference： [1]Chen, Chien-Tien; Munot, Yogesh S. [Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8625 - 8627]

14
[ 67-56-1 ]
[ 464-78-8 ]
ketopinic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With boron trifluoride at 65℃; for 0.333333h;
61%	With indium(III) chloride for 96h; Heating;

Reference： [1]Jaoui; Kleindienst; Lewandowski; Edney [Analytical Chemistry, 2004, vol. 76, # 16, p. 4765 - 4778]
[2]Mineno, Tomoko; Kansui, Hisao [Chemical and Pharmaceutical Bulletin, 2006, vol. 54, # 6, p. 918 - 919]

15
[ 464-78-8 ]
[ 7112-38-1 ]
(S)-(+)-3-(3-picolyl)-10,10-dimethyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-en-2-one [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 11644 - 11655

16
[ 464-78-8 ]
(1S,4R)-7,7-Dimethyl-2-[(E)-pentafluorophenylmethoxyimino]-bicyclo[2.2.1]heptane-1-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / BF₃ / 0.33 h / 65 °C 2: water / 24 h / 20 °C

Reference： [1]Jaoui; Kleindienst; Lewandowski; Edney [Analytical Chemistry, 2004, vol. 76, # 16, p. 4765 - 4778]

17
[ 464-78-8 ]
i-propyl 7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 87 percent / diphenylphosphoryl azide; triethylamine / toluene / 0.5 h / Heating 2: 87 percent / titanium tetra-t-butoxide / benzene / 24 h / 25 °C

Reference： [1]Spino, Claude; Joly, Marc-Andre; Godbout, Cedrickx; Arbour, Melissa [Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6118 - 6121]

18
[ 464-78-8 ]
t-butyl 7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 87 percent / diphenylphosphoryl azide; triethylamine / toluene / 0.5 h / Heating 2: 56 percent / titanium tetra-t-butoxide / benzene / 96 h / 120 °C

Reference： [1]Spino, Claude; Joly, Marc-Andre; Godbout, Cedrickx; Arbour, Melissa [Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6118 - 6121]

19
[ 464-78-8 ]
neo-pentyl 7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 87 percent / diphenylphosphoryl azide; triethylamine / toluene / 0.5 h / Heating 2: 92 percent / titanium tetra-t-butoxide / benzene / 24 h / 25 °C

Reference： [1]Spino, Claude; Joly, Marc-Andre; Godbout, Cedrickx; Arbour, Melissa [Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 6118 - 6121]

20
[ 464-78-8 ]
7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂; DMAP / CH₂Cl₂ 2: CH₂Cl₂ / 20 °C 3: AIBN / benzene / 80 °C
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere; Reflux 2: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

Reference： [1]Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Scialpi, Rosanna; Spagnolo, Piero; Zanardi, Giuseppe [Synlett, 2004, # 6, p. 985 - 990]
[2]Sui, Guoqing; Lv, Qingyun; Song, Xiaoqing; Guo, Huihui; Dai, Jiatong; Ren, Li; Lee, Chi-Sing; Zhou, Wenming; Hao, Hong-Dong [New Journal of Chemistry, 2019, vol. 43, # 39, p. 15793 - 15796]

21
[ 464-78-8 ]
[ 728880-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂; DMAP / CH₂Cl₂ 2: CH₂Cl₂ / 20 °C

Reference： [1]Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Scialpi, Rosanna; Spagnolo, Piero; Zanardi, Giuseppe [Synlett, 2004, # 6, p. 985 - 990]

22
[ 464-78-8 ]
[ 933-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N₂H₄*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 205 °C 2: (i) AgNO₃, aq. NH₃, (ii) I₂, cyclohexane

Reference： [1]Bunce,N.J.; Murray,N.G. [Tetrahedron, 1971, vol. 27, p. 5323 - 5335]

23
camphor-10-sulfonic acid [ No CAS ]
[ 464-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂, CaCO₃ 2: TsCl, Py / dioxane 3: KMnO₄, aq. Na₂CO₃ / acetone

Reference： [1]Bunce,N.J.; Murray,N.G. [Tetrahedron, 1971, vol. 27, p. 5323 - 5335]

24
[ 4552-50-5 ]
[ 464-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: TsCl, Py / dioxane 2: KMnO₄, aq. Na₂CO₃ / acetone

Reference： [1]Bunce,N.J.; Murray,N.G. [Tetrahedron, 1971, vol. 27, p. 5323 - 5335]

25
[ 464-78-8 ]
[ 35122-25-9 ]