{(1S,2S)-trans-2-methylcyclohexyl}dichloroborane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: {(1S,2S)-trans-2-methylcyclohexyl}dichloroborane
• 英文别名: dichloro-[(1S,2S)-2-methylcyclohexyl]borane
• 化学式: C₇H₁₃BCl₂
• 分子量: 178.897
• InChiKey: NZZZDSWHEUTZCA-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  10
• 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

• 作为产物：
  描述：

  (1S,2S)-diethyl trans-(2-methylcyclohexyl)boronate 、 三氯化硼 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到{(1S,2S)-trans-2-methylcyclohexyl}dichloroborane
  参考文献：
  名称：

  有机oboranes。55.改进了将代表性的非手性和手性烷基-，（E）-1-烯基和（Z）-1-烯基-以及芳基硼酸酯转化为相应的有机基二氯硼烷的方法

  摘要：

  Diethyl alkylboronates, R*B(OEt)2, of essentially 100% enantiomeric purity, prepared by asymmetric hydroboration of readily available prochiral alkenes, were effectively converted into the corresponding chiral alkyldichloroboranes, R*BCl2, by treatment with boron trichloride (1 M solution in dichloromethane) in the presence of a catalytic amount of anhydrous ferric chloride (3 mol %). This reaction is quite general, proceeds well without detectable racemization, and is applicable to essentially optically pure boronic esters of widely varied structural requirements. The reaction is also applicable to achiral boronates, such as 1-hexyl, and hindered alkyl, such as tert-butyl. It is also applicable to the conversion of (E)- and (Z)-1-hexenylboronates, representative of the 1-alkenyl derivatives, and to phenylboronates, representative of aryl derivatives. Consequently, this procedure appears to be broadly applicable to the conversion of organylboronates, RB(OR')2, into the corresponding organyldichloroboranes, RBCl2.

  DOI：

  10.1021/om00045a025

文献信息

• Organoboranes. 55. Improved procedure for the conversion of representative achiral and chiral alkyl-, (E)-1-alkenyl and (Z)-1-alkenyl-, and arylboronates into the corresponding organyldichloroboranes
  作者：Herbert C. Brown、Ashok M. Salunkhe、Ankush B. Argade

  DOI：10.1021/om00045a025

  日期：1992.9

  Diethyl alkylboronates, R*B(OEt)2, of essentially 100% enantiomeric purity, prepared by asymmetric hydroboration of readily available prochiral alkenes, were effectively converted into the corresponding chiral alkyldichloroboranes, R*BCl2, by treatment with boron trichloride (1 M solution in dichloromethane) in the presence of a catalytic amount of anhydrous ferric chloride (3 mol %). This reaction is quite general, proceeds well without detectable racemization, and is applicable to essentially optically pure boronic esters of widely varied structural requirements. The reaction is also applicable to achiral boronates, such as 1-hexyl, and hindered alkyl, such as tert-butyl. It is also applicable to the conversion of (E)- and (Z)-1-hexenylboronates, representative of the 1-alkenyl derivatives, and to phenylboronates, representative of aryl derivatives. Consequently, this procedure appears to be broadly applicable to the conversion of organylboronates, RB(OR')2, into the corresponding organyldichloroboranes, RBCl2.