(S)-3-[(methyldiphenylsilyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phthalimido-4-pentene | 1170729-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-3-[(methyldiphenylsilyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phthalimido-4-pentene
• 英文别名: 2-[(3S)-3-[[methyl(diphenyl)silyl]methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enyl]isoindole-1,3-dione
• CAS: 1170729-12-0
• 化学式: C₃₃H₃₈BNO₄Si
• 分子量: 551.566
• InChiKey: RBDCBOGQOOYJME-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-phthalimidoethyl)-1-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 96.0h， 生成 、 (R)-2-(3-(methyldiphenylsilyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-5-en-1-yl)isoindoline-1,3-dione 、 (R)-3-[(methyldiphenylsilyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phthalimido-4-pentene 、 (S)-3-[(methyldiphenylsilyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phthalimido-4-pentene
  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