trans-1-bromo-2-methyl-2-cyanocyclopropane | 78004-14-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-1-bromo-2-methyl-2-cyanocyclopropane
• 英文别名: 2-bromo-1-methylcyclopropanecarbonitrile；(1S,2R)-2-bromo-1-methylcyclopropane-1-carbonitrile
• CAS: 78004-14-5
• 化学式: C₅H₆BrN
• 分子量: 160.013
• InChiKey: GWLMXYSPZBXXQY-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2-二溴-1-甲基环丙烷甲腈 在 异丙基氯化镁 、 ammonium chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.08h， 以76%的产率得到trans-1-bromo-2-methyl-2-cyanocyclopropane
  参考文献：
  名称：

  Stereoselective Functionalization of Cyclopropane Derivatives Using Bromine/Magnesium and Sulfoxide/Magnesium Exchange Reactions

  摘要：

  The reaction of 2,2-dibromo-l-methyl-cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.

  DOI：

  10.1021/ol051452p

文献信息

• Reaction of gem-dibromocyclopropanes with potassium dimethyl phosphite in liquid ammonia. A highly stereoselective reduction
  作者：Gordon F. Meijs、Ian R. Doyle

  DOI：10.1021/jo00220a008

  日期：1985.10
• A novel system consisting of low valent vanadium and diethyl phosphonate or triethyl phosphite for the highly stereoselective reduction of gem-dibromocyclopropanes
  作者：Toshikazu Hirao、Keisuke Hirano、Takeya Hasegawa、Yoshiki Ohshiro、Isao Ikeda

  DOI：10.1021/jo00075a070

  日期：1993.11
• Electrochemical reduction of 1,1-dihalo-2,2-disubstituted cyclopropanes
  作者：Yu. M. Kargin、E. I. Gritsenko、V. V. Yanilkin、V. V. Plemenkov、L. K. Dubovik、N. I. Maksimyuk、B. M. Garifullin、Sh. K. Letypov、A. V. Il'yasov

  DOI：10.1007/bf00863575

  日期：1992.9

  The electrochemical reduction of 1,1-dihalo-2-R-2-methylcyclopropanes was studied by polarography and preparative electrolysis. A mixture of stereoisomeric monoboro- and monochlorocyclopropanes was obtained with preparative yield of 60-70% in preparative electroreduction in methanol against a background of 0.1 M LiClO4. In the case of bromine derivatives of cyclopropanes (except when R = CN) an effect was found on the part of the current density on the ratio of cis and trans isomers, which was interpreted as a change, in dependence on current density, of the contributions of the reactions of reduction of the starting compounds (SN2 mechanism) and ionic pairs (S(N)1 mechanism). The effect of the solvent (CHCl3, DMF, DMSO, MeOH) and background salt (LiClO4, Et4NBr) on the ratio of stereoisomers is in agreement with this interpretation.
• Stereoselective Functionalization of Cyclopropane Derivatives Using Bromine/Magnesium and Sulfoxide/Magnesium Exchange Reactions
  作者：Felix Kopp、Genia Sklute、Kurt Polborn、Ilan Marek、Paul Knochel

  DOI：10.1021/ol051452p

  日期：2005.8.1

  The reaction of 2,2-dibromo-l-methyl-cyclopropanecarbonitrile (1) with i-PrMgCl in Et2O/CH2Cl2 provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved.