(1R,2S)-2-(Dimethyl-phenyl-silanyl)-1-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol | 611236-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2-(Dimethyl-phenyl-silanyl)-1-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol
• 英文别名: (1R,2S)-2-[dimethyl(phenyl)silyl]-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol
• CAS: 611236-40-9
• 化学式: C₁₉H₂₈O₃Si
• 分子量: 332.515
• InChiKey: IYRWRQQFVBCYKV-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(Dimethyl-phenyl-silanyl)-1-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid (3aS,4R,5S,7aS)-5-(dimethyl-phenyl-silanyl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  An allylation-metathesis sequence as a convergent strategy towards enantiopure equivalents of highly functionalized cyclic dienes

  摘要：

  Highly enantioenriched equivalents of cyclic dienes have been readily prepared by asymmetric allylation of unsaturated aldehydes using a chiral allyltitanium reagent, followed by a ring-closing metathesis. The resulting beta-hydroxy allylsilanes react stereoselectively with a wide variety of electrophilic reagents. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01791-x
• 作为产物：
  描述：

  烯丙基二甲基苯基硅烷 、 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 在 正丁基锂 、 Cp((R,R)-TADDOL)TiCl 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 以55%的产率得到(1R,2S)-2-(Dimethyl-phenyl-silanyl)-1-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol
  参考文献：
  名称：

  An allylation-metathesis sequence as a convergent strategy towards enantiopure equivalents of highly functionalized cyclic dienes

  摘要：

  Highly enantioenriched equivalents of cyclic dienes have been readily prepared by asymmetric allylation of unsaturated aldehydes using a chiral allyltitanium reagent, followed by a ring-closing metathesis. The resulting beta-hydroxy allylsilanes react stereoselectively with a wide variety of electrophilic reagents. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01791-x

文献信息

• An allylation-metathesis sequence as a convergent strategy towards enantiopure equivalents of highly functionalized cyclic dienes
  作者：Laurence de Fays、Jean-Michel Adam、Léon Ghosez

  DOI：10.1016/s0040-4039(03)01791-x

  日期：2003.9

  Highly enantioenriched equivalents of cyclic dienes have been readily prepared by asymmetric allylation of unsaturated aldehydes using a chiral allyltitanium reagent, followed by a ring-closing metathesis. The resulting beta-hydroxy allylsilanes react stereoselectively with a wide variety of electrophilic reagents. (C) 2003 Elsevier Ltd. All rights reserved.