CAS: 96847-52-8; (1R,5S)-1-Phenyl-3-Oxabicyclo[3.1.0]Hexan-2-One

英文名称(1R,5S)-1-Phenyl-3-Oxabicyclo[3.1.0]Hexan-2-One
中文名称(1R,5S)-1-苯基-3-.[3.1.0]己烷-2-酮
IUPAC名称(1R,5S)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one
其它别名(1R,5S)-1-Phenyl-3-Oxabicyclo[3.1.0]Hexan-2-One; Milnacipran Hydrochloride Impurity 1; 3-Oxabicyclo[3.1.0]Hexan-2-One, 1-Phenyl-, (1R,5S)-; Milcipranimpurity10; Mirapram Impurity 12
CAS编号96847-52-8
MFCD编号:MFCD28348389
分子式:C11H10O2分子量:174.2
产品CID: 2019088
产品分类Chemistry → Asymmetric Synthesis → Chiral Building Blocks | Esters | Other Aliphatic Heterocycles

相似结构搜索
InChIKey: WZGFIZUMKYUMRN-KOLCDFICSA-N
InChI=1S/C11H10O2/c12-10-11(6-9(11)7-13-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2/t9-,11+/m1/s1
计算化学: 氢键受体数*氢键供体数*可旋转键数*

物理性质

PSA:26.3
LogP:1.5011
溶解性Chloroform (Slightly), Methanol (Slightly)
外观形态淡黄色至浅橙色固体

MSDS等安全信息

合成工艺路线路线简述

合成目标产物 (1R,5S)-1-Phenyl-3-Oxabicyclo[3.1.0]Hexan-2-One 主要起始原料 Allyl Alpha-Diazophenylacetate
145193-16-4 = 96847-52-8
反应条件:1.1 Catalysts: Rhodium,Tetrakis[μ-[methyl (2S)-4-(Oxo-Ko)-2-Azetidinecarboxylato-Kn1]]Di-,(Rh... Solvents: Dichloromethane; 2 H,Reflux
标题:Comparative Enantiocontrol With Allyl Phenyldiazoacetates In Asymmetric Catalytic Intramolecular Cyclopropanation
作者:Doyle,Michael P.; Hu,Wenhao; Weathers,Thomas M. Jr.
参考文献:Chirality 日期:2003 卷标:15(4) 页码:369-373]

145193-16-4 = 96847-52-8
反应条件:1.1 Catalysts: Rhodium,Tetrakis[μ-[methyl (2S)-4-(Oxo-Ko)-2-Azetidinecarboxylato-Kn1]]Di-,(Rh... Solvents: Dichloromethane
标题:A New Enantioselective Synthesis Of Milnacipran And An Analogue By Catalytic Asymmetric Cyclopropanation
作者:Doyle,Michael P.; Hu,Wenhao
参考文献:Advanced Synthesis & Catalysis 日期:2001 卷标:343(3) 页码:299-302]

66823-04-9 = 96847-52-8 [标题:Reaction Conditions
标题:1-Phenyl-2-(Hydroxymethyl)Cyclopropanecarboxylic Acid And Derivatives
作者:Casadio,S.; Bonnaud,B.; Mouzin,G.; Cousse,H.
参考文献:Bollettino Chimico Farmaceutico 日期:1978 卷标:117(6) 页码:331-42]

910028-42-1 = 96847-52-8
反应条件:1.1 Reagents: Sodium Hydride Solvents: Water; 6 H,90 - 100 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 4 H,Ph 1 - 2,60 - 70 °C1.3 Reagents: Sodium Bicarbonate Solvents: Water
标题:A Process For The Preparation Of Dextromilnacipran Or Its Salt Thereof
参考文献:India]

= 96847-52-8 [标题:Reaction Conditions
标题:Improved Process For The Preparation Of Levomilnacipran
参考文献:World Intellectual Property Organization]

= 96847-52-8 [标题:Reaction Conditions
标题:Stereocontrolled Synthesis Of Trisubstituted Cyclopropanes: Expedient,Atom-Economical,Asymmetric Syntheses Of (+)-Bicifadine And Dov21947
作者:Xu,Feng; Murry,Jerry A.; Simmons,Bryon; Corley,Edward; Fitch,Kenneth; Et Al
参考文献:Organic Letters 日期:2006 卷标:8(17) 页码:3885-3888]

= 96847-52-8 [标题:Reaction Conditions
标题:Synthesis Of (+)- And (-)-Milnacipran And Their Conformationally Restricted Analogs
作者:Shuto,Satoshi; Ono,Shizuka; Hase,Yukako; Kamiyama,Noriko; Matsuda,Akira
参考文献:Tetrahedron Letters 日期:1996 卷标:37(5) 页码:641-4]

67843-74-7 = 96847-52-8 + 1932011-41-0
反应条件:1.1 Reagents: Sodium Amide Solvents: Benzene; 0 °C; 3 H,Rt1.2 Solvents: Benzene; 2 H,Rt1.3 Reagents: Potassium Hydroxide Solvents: Ethanol; 15 H,Reflux; 30 Min,150 °C; 45 Min,15 Mm Hg,150 °C
标题:(+)-Methyl (1R,2S)-2-{[4-(4-Chlorophenyl)-4-Hydroxypiperidin-1-Yl]Methyl}-1-Phenylcyclopropanecarboxylate [(+)-Mr200] Derivatives As Potent And Selective Sigma Receptor Ligands: Stereochemistry And Pharmacological Properties
作者:Amata,Emanuele; Rescifina,Antonio; Prezzavento,Orazio; Arena,Emanuela; Dichiara,Maria; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2018 卷标:61(1) 页码:372-384]

= 96847-52-8 + 1973459-72-1
反应条件:1.1 Reagents: Lithium Bis(Trimethylsilyl)Amide Solvents: Toluene,Tetrahydrofuran; 10 Min,Rt; 20 Min,Rt1.2 Reagents: Monosodium Phosphate Solvents: Water; Rt
标题:Synthesis Of Enantiopure Cyclopropyl Esters From (-)-Levoglucosenone
作者:Stockton,Kieran P.; Greatrex,Ben W.
参考文献:Organic & Biomolecular Chemistry 日期:2016 卷标:14(31) 页码:7520-7528]

67843-74-7 = 96847-52-8
反应条件:1.1 Reagents: Sodium Amide Solvents: Benzene; 7 Min,Cooled; 1 H,Rt1.2 Solvents: Benzene; 20 Min,Cooled; 20 Min,Cooled1.3 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 19 H,Reflux
标题:Preparation Of Pyrimidinylcyclopropane Derivatives Having Bace1 Inhibiting Activity
参考文献:World Intellectual Property Organization]

67843-74-7 = 96847-52-8
反应条件:1.1 Reagents: Sodium Amide Solvents: Benzene; 30 Min,< 20 °C; 30 Min,Rt1.2 Solvents: Benzene; 25 Min,< 20 °C; 30 Min,Rt1.3 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 8 H,Reflux
标题:Conformational Restriction Approach To β-Secretase (Bace1) Inhibitors: Effect Of A Cyclopropane Ring To Induce An Alternative Binding Mode
作者:Yonezawa,Shuji; Yamamoto,Takahiko; Yamakawa,Hidekuni; Muto,Chie; Hosono,Motoko; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2012 卷标:55(20) 页码:8838-8858]

145193-16-4 = 96847-52-8
反应条件:1.1 Catalysts: Ferrous Perchlorate,Sodium Tetrakis[3,5-Bis(Trifluoromethyl)Phenyl]Borate,(4S,4′s)-2,2′-[(1R)-2,2′,3,3′-Tetrahydro-1,1′-Spirobi[1H-Indene]-7,7′-Diyl]Bis[4... Solvents: Chloroform; 4 H,Rt1.2 30 H,60 °C
标题:Enantioselective Iron-Catalyzed Intramolecular Cyclopropanation Reactions
作者:Shen,Jun-Jie; Zhu,Shou-Fei; Cai,Yan; Xu,Huan; Xie,Xiu-Lan; Et Al
参考文献:Angewandte Chemie 日期:2014 卷标:53(48) 页码:13188-13191]

67843-74-7 = 96847-52-8
反应条件:1.1 Reagents: Sodium Amide Solvents: Benzene; 0 °C; 3 H,Rt1.2 0 °C; 2 H,Rt1.3 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; Overnight,Reflux1.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,0 °C
标题:Synthesis Of Enantiomerically Pure Milnacipran Analogs And Inhibition Of Dopamine,Serotonin,And Norepinephrine Transporters
作者:Roggen,Heidi; Kehler,Jan; Stensbol,Tine Bryan; Hansen,Tore
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2007 卷标:17(10) 页码:2834-2837]

70209-83-5 = 96847-52-8
反应条件:1.1 150 °C
标题:In Vivo And In Vitro Olefin Cyclopropanation Catalyzed By Engineered And Chimeric Heme Enzymes
参考文献:World Intellectual Property Organization]

67843-74-7 = 96847-52-8 [标题:Reaction Conditions
标题:Synthesis Of 1-Arylpiperazyl-2-Phenylcyclopropanes Designed As Antidopaminergic Agents: Cyclopropane-Based Conformationally Restricted Analogs Of Haloperidol
作者:Yamaguchi,Kazuya; Kazuta,Yuji; Hirano,Kazufumi; Yamada,Shizuo; Matsuda,Akira; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2008 卷标:16(19) 页码:8875-8881]

= 96847-52-8 [标题:Reaction Conditions
标题:Studies On The Structure-Activity Relationship Of Bicifadine Analogs As Monoamine Transporter Inhibitors
作者:Zhang,Mingzhu; Jovic,Florence; Vickers,Troy; Dyck,Brian; Tamiya,Junko; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2008 卷标:18(13) 页码:3682-3686]

= 96847-52-8 [标题:Reaction Conditions
标题:Synthesis,Stereochemistry,And Chiroptical Spectra Of Cyclopropyl Lactones And Thionolactones
作者:Milewska,Maria J.; Gdaniec,Maria; Polonski,Tadeusz
参考文献:Tetrahedron: Asymmetry 日期:1996 卷标:7(11) 页码:3169-3180]

63106-93-4 = 96847-52-8 + 96847-53-9
反应条件:1.1 Solvents: Dimethylformamide,Water; 41 H,Ph 8,27 °C; Acidified
标题:Microbiological Transformations. 34. Enantioselective Hydrolysis Of A Key-Lactone Involved In The Synthesis Of The Antidepressant Milnacipran
作者:Viazzo,Pascale; Alphand,Veronique; Furstoss,Roland
参考文献:Tetrahedron Letters 日期:1996 卷标:37(26) 页码:4519-4522