1-[(triisopropylsilyloxy)methyl]indoline-2,3-dione | 1185745-52-1

• 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: 1-[(triisopropylsilyloxy)methyl]indoline-2,3-dione
• 英文别名: 1-[Tri(propan-2-yl)silyloxymethyl]indole-2,3-dione
• CAS: 1185745-52-1
• 化学式: C₁₈H₂₇NO₃Si
• 分子量: 333.503
• InChiKey: XTQXSBTXEYXHFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  靛红 、 (异丙氧基硅)氯甲烷 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以25%的产率得到1-[(triisopropylsilyloxy)methyl]indoline-2,3-dione
  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

文献信息

• Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of <i>ent</i>-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B
  作者：Takahiko Itoh、Hayato Ishikawa、Yujiro Hayashi

  DOI：10.1021/ol901432a

  日期：2009.9.3

  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.