(R)-2-(3-hydroxy-2-oxo-1-((triisopropylsilyloxy)methyl)indolin-3-yl)ethyl methanesulfonate | 1185745-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-2-(3-hydroxy-2-oxo-1-((triisopropylsilyloxy)methyl)indolin-3-yl)ethyl methanesulfonate
• 英文别名: 2-[(3R)-3-hydroxy-2-oxo-1-[tri(propan-2-yl)silyloxymethyl]indol-3-yl]ethyl methanesulfonate
• CAS: 1185745-45-2
• 化学式: C₂₁H₃₅NO₆SSi
• 分子量: 457.663
• InChiKey: QSSUCBBTAQQVOL-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-(3-hydroxy-2-oxo-1-((triisopropylsilyloxy)methyl)indolin-3-yl)ethyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到(R)-3-(2-azidoethyl)-3-hydroxy-1-((triisopropylsilyloxy)methyl)indolin-2-one
  参考文献：
  名称：

  Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of ent-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B

  摘要：

  The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hydroxyindole alkaloids. Short syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B have been accomplished.

  DOI：

  10.1021/ol901432a
• 作为产物：
  描述：

  (R)-3-hydroxy-3-(2-hydroxyethyl)-1-((triisopropylsilyloxy)methyl)indolin-2-one 、 甲基磺酰氯 在 吡啶 作用下， 以75%的产率得到(R)-2-(3-hydroxy-2-oxo-1-((triisopropylsilyloxy)methyl)indolin-3-yl)ethyl methanesulfonate
  参考文献：
  名称：

  Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of ent-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B

  摘要：

  The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hydroxyindole alkaloids. Short syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B have been accomplished.

  DOI：

  10.1021/ol901432a