(R)-3-hydroxy-3-(2-hydroxyethyl)-1-((triisopropylsilyloxy)methyl)indolin-2-one | 1185745-55-4

• 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)-3-hydroxy-3-(2-hydroxyethyl)-1-((triisopropylsilyloxy)methyl)indolin-2-one
• 英文别名: (3R)-3-hydroxy-3-(2-hydroxyethyl)-1-[tri(propan-2-yl)silyloxymethyl]indol-2-one
• CAS: 1185745-55-4
• 化学式: C₂₀H₃₃NO₄Si
• 分子量: 379.572
• InChiKey: IUHURNLNOKXVAQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-3-(2-hydroxyethyl)-1-((triisopropylsilyloxy)methyl)indolin-2-one 在 甲醇 、 氟化铵 作用下， 以88%的产率得到(R)-3-hydroxy-3-(2-hydroxyethyl)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：

  1-[(triisopropylsilyloxy)methyl]indoline-2,3-dione 、 乙醛 在 (3R,5S)-5-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)pyrrolidin-3-ol 、 氯乙酸 、 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 73.0h， 生成 (R)-3-hydroxy-3-(2-hydroxyethyl)-1-((triisopropylsilyloxy)methyl)indolin-2-one 、 (S)-3-hydroxy-3-(2-hydroxyethyl)-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