cis-1-Bromo-2,2,3-trimethylcyclopropane | 3815-07-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: cis-1-Bromo-2,2,3-trimethylcyclopropane
• 英文别名: 1-Brom-cis-2,2,3-trimethylcyclopropan；syn-1-Brom-2,2,3-trimethylcyclopropan；1-Brom-2,2,3-trimethyl-cyclopropan；(2R,3R)-2-bromo-1,1,3-trimethylcyclopropane
• CAS: 3815-07-4
• 化学式: C₆H₁₁Br
• 分子量: 163.057
• InChiKey: SYYSPTZPJSFOQY-CRCLSJGQSA-N

物化性质

• 沸点：
  120.8±9.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 、 cis-1-Bromo-2,2,3-trimethylcyclopropane 在 四甲基乙二胺 、 叔丁基锂 作用下， 生成 (1R,2S)-2-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-1-[(1R,3S)-2,2,3-trimethylcyclopropyl]propan-1-ol 、 (1R,2S)-2-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-1-[(1S,3R)-2,2,3-trimethylcyclopropyl]propan-1-ol
  参考文献：
  名称：

  Two new approaches to the 25-hydroxy-vitamin D2 side chain

  摘要：

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.

  DOI：

  10.1021/jo00033a021
• 作为产物：
  描述：

  1,1-dibromo-2,2,3-trimethylcyclopropane 在 三正丁基氢锡 作用下， 生成 cis-1-Bromo-2,2,3-trimethylcyclopropane
  参考文献：
  名称：

  Cyclopropyl solvolyses. IV. Leaving group and alkyl substitution effects in monocyclic systems

  摘要：

  DOI：

  10.1021/ja00756a025

文献信息

• Oxygen-accelerated Generation of the Bromocarbenoid Reagent of Zinc from Diethylzinc and Bromoform. Bromocyclopropanes from Olefins
  作者：Sotaro Miyano、Harukichi Hashimoto

  DOI：10.1246/bcsj.48.3665

  日期：1975.12

  Oxygen greatly accelerates the generation of the bromocarbenoid reagent of zinc from diethylzinc and bromoform. Olefins, including cyclohexene, cyclooctene, 1-hexene, cis- and trans-2-butene, isobu...

  氧气大大加速了二乙基锌和溴仿生成锌的溴代卡宾试剂。烯烃，包括环己烯、环辛烯、1-己烯、顺式和反式-2-丁烯、异丁烯...
• 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
• The Halogenation of Diazomethane. Study of the Reactivities of Carbenes Derived from Halodiazomethanes^1-3
  作者：G. L. Closs、J. J. Coyle

  DOI：10.1021/ja00947a010

  日期：1965.10
• Two new approaches to the 25-hydroxy-vitamin D2 side chain
  作者：Stephen R. Wilson、Andrew E. Davey、Maria E. Guazzaroni

  DOI：10.1021/jo00033a021

  日期：1992.3

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.
• Cyclopropyl solvolyses. IV. Leaving group and alkyl substitution effects in monocyclic systems
  作者：W. F. Sliwinski、T. M. Su、P. von R. Schleyer

  DOI：10.1021/ja00756a025

  日期：1972.1