(1S,2S)-diethyl trans-(2-methylcyclohexyl)boronate | 112398-76-2

• 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)-diethyl trans-(2-methylcyclohexyl)boronate
• 英文别名: diethoxy-[(1S,2S)-2-methylcyclohexyl]borane
• CAS: 112398-76-2
• 化学式: C₁₁H₂₃BO₂
• 分子量: 198.113
• InChiKey: GOWXIMDXNBXQKE-QWRGUYRKSA-N

物化性质

• 沸点：
  215.8±7.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S)-diethyl trans-(2-methylcyclohexyl)boronate 以 水 为溶剂， 生成 [(1S,2S)-2-methylcyclohexyl]boronic acid
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 12. Conversion of boronic esters of essentially 100% optical purity into monoalkylthexylboranes providing convenient synthetic routes to trans-olefins, cis-olefins, alkynes, and ketones of very high enantiomeric purities

  摘要：

  DOI：

  10.1021/ja00213a028
• 作为产物：
  描述：

  (1S,2S)-trans-isopinocampheyl-(2-methylcyclohexyl)borane 、 乙醛 生成 (1S,2S)-diethyl trans-(2-methylcyclohexyl)boronate
  参考文献：
  名称：

  BROWN, HERBERT C.;BAKSHI, RAMAN K.;SINGARAM, BAKTHAN, J. AMER. CHEM. SOC., 110,(1988) N 5, 1529-1534

  摘要：

  DOI：

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.
• Chiral synthesis via organoboranes. 12. Conversion of boronic esters of essentially 100% optical purity into monoalkylthexylboranes providing convenient synthetic routes to trans-olefins, cis-olefins, alkynes, and ketones of very high enantiomeric purities
  作者：Herbert C. Brown、Raman K. Bakshi、Bakthan. Singaram

  DOI：10.1021/ja00213a028

  日期：1988.3
• BROWN, HERBERT C.;BAKSHI, RAMAN K.;SINGARAM, BAKTHAN, J. AMER. CHEM. SOC., 110,(1988) N 5, 1529-1534
  作者：BROWN, HERBERT C.、BAKSHI, RAMAN K.、SINGARAM, BAKTHAN

  DOI：——

  日期：——