(1R,2R,3R,5E)-1,5-diphenyl-3-triisopropylsilyloxy-1,2-epoxy-5-pentene | 352000-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3R,5E)-1,5-diphenyl-3-triisopropylsilyloxy-1,2-epoxy-5-pentene
• 英文别名: [(E,1R)-3-phenyl-1-[(2S,3R)-3-phenyloxiran-2-yl]prop-2-enoxy]-tri(propan-2-yl)silane
• CAS: 352000-41-0
• 化学式: C₂₆H₃₆O₂Si
• 分子量: 408.656
• InChiKey: VVQFHJXYTCTXBE-XMNNPDTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5E)-1,5-diphenyl-3-triisopropylsilyloxy-1,2-epoxy-5-pentene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以80%的产率得到(1R,2R,3R,5E)-1,5-diphenyl-1,2-epoxy-5-penten-3-ol
  参考文献：
  名称：

  Substrate Binding in the Asymmetric Dihydroxylation Reaction − Investigation of the Stereoselectivity in the Dihydroxylation ofCs-Symmetric Divinylcarbinol Derivatives

  摘要：

  The mechanism of the asymmetric dihydroxylation (AD) reaction has been hotly disputed. We have studied the stereochemical outcome of the AD reaction on a series of C-s-symmetric divinylcarbinol derivatives in order to shed Light on the binding mode of the substrate to the osmium tetroxide-ligand complex. The product distribution is dependent on the size of the allylic substituent, and on the type and class of ligand. It is postulated that the diastereospecificity of the reactions originates from attractive forces between the substrate and the ligand. These interactions are independent of the interactions responsible for the enantioselectivity in the AD reaction.

  DOI：

  10.1002/1099-0690(200105)2001:9<1769::aid-ejoc1769>3.0.co;2-d
• 作为产物：
  描述：

  联甲基苯乙烯酮 在 原乙酸三甲酯 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 potassium dioxotetrahydroxoosmate(VI) 、 silver nitrate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 55.0h， 生成 (1R,2R,3R,5E)-1,5-diphenyl-3-triisopropylsilyloxy-1,2-epoxy-5-pentene
  参考文献：
  名称：

  Substrate Binding in the Asymmetric Dihydroxylation Reaction − Investigation of the Stereoselectivity in the Dihydroxylation ofCs-Symmetric Divinylcarbinol Derivatives

  摘要：

  The mechanism of the asymmetric dihydroxylation (AD) reaction has been hotly disputed. We have studied the stereochemical outcome of the AD reaction on a series of C-s-symmetric divinylcarbinol derivatives in order to shed Light on the binding mode of the substrate to the osmium tetroxide-ligand complex. The product distribution is dependent on the size of the allylic substituent, and on the type and class of ligand. It is postulated that the diastereospecificity of the reactions originates from attractive forces between the substrate and the ligand. These interactions are independent of the interactions responsible for the enantioselectivity in the AD reaction.

  DOI：

  10.1002/1099-0690(200105)2001:9<1769::aid-ejoc1769>3.0.co;2-d

文献信息

• Substrate Binding in the Asymmetric Dihydroxylation Reaction − Investigation of the Stereoselectivity in the Dihydroxylation ofCs-Symmetric Divinylcarbinol Derivatives
  作者：Annette Bayer、John S. Svendsen

  DOI：10.1002/1099-0690(200105)2001:9<1769::aid-ejoc1769>3.0.co;2-d

  日期：2001.5

  The mechanism of the asymmetric dihydroxylation (AD) reaction has been hotly disputed. We have studied the stereochemical outcome of the AD reaction on a series of C-s-symmetric divinylcarbinol derivatives in order to shed Light on the binding mode of the substrate to the osmium tetroxide-ligand complex. The product distribution is dependent on the size of the allylic substituent, and on the type and class of ligand. It is postulated that the diastereospecificity of the reactions originates from attractive forces between the substrate and the ligand. These interactions are independent of the interactions responsible for the enantioselectivity in the AD reaction.