(S)-4-(methyldiphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-decene | 1170729-05-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-4-(methyldiphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-decene
• 英文别名: methyl-diphenyl-[(4S)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dec-1-en-4-yl]silane
• CAS: 1170729-05-1
• 化学式: C₂₉H₄₃BO₂Si
• 分子量: 462.556
• InChiKey: RUUVYBPPEVUYCA-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-n-hexyl-2-methylenecyclopropane 、 2-(methyldiphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 N,N-Bis((R)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 92.0h， 生成 (R)-4-(methyldiphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-decene 、 (S)-4-(methyldiphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-decene 、 (S)-3-[(methyldiphenylsilyl)methyl]-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-nonene
  参考文献：
  名称：

  Kinetic Resolution of Racemic 1-Alkyl-2-methylenecyclopropanes via Palladium-Catalyzed Silaborative C−C Cleavage

  摘要：

  Kinetic resolution of racemic 1-alkyl-2-methylenecyclopropanes via silaborative C-C cleavage was efficiently catalyzed by a palladium complex bearing a chiral phosphoramidite, affording 2-boryl-3-silylmethyl-1-alkenes as major products with up to 92% ee. Enantioenrichment through parallel kinetic resolution, where the slower reacting enantiomer was converted to the constitutional isomer of the major product, may be involved as the crucial stereodiscriminating step.

  DOI：

  10.1021/ol900829c

文献信息

• Kinetic Resolution of Racemic 1-Alkyl-2-methylenecyclopropanes via Palladium-Catalyzed Silaborative C−C Cleavage
  作者：Toshimichi Ohmura、Hiroki Taniguchi、Michinori Suginome

  DOI：10.1021/ol900829c

  日期：2009.7.2

  Kinetic resolution of racemic 1-alkyl-2-methylenecyclopropanes via silaborative C-C cleavage was efficiently catalyzed by a palladium complex bearing a chiral phosphoramidite, affording 2-boryl-3-silylmethyl-1-alkenes as major products with up to 92% ee. Enantioenrichment through parallel kinetic resolution, where the slower reacting enantiomer was converted to the constitutional isomer of the major product, may be involved as the crucial stereodiscriminating step.