3,8-Bis-(tert-butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-1-[3-methyl-3-((S)-3-methyl-pentyl)-oxiranyl]-9H-carbazole | 909708-80-1

• 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: 3,8-Bis-(tert-butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-1-[3-methyl-3-((S)-3-methyl-pentyl)-oxiranyl]-9H-carbazole
• 英文别名: [1,6-bis[[tert-butyl(diphenyl)silyl]oxy]-7-methyl-8-[3-methyl-3-[(3S)-3-methylpentyl]oxiran-2-yl]-9H-carbazol-4-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 909708-80-1
• 化学式: C₇₁H₈₃NO₄Si₃
• 分子量: 1098.7
• InChiKey: ADRHQSVERLJDJX-TUEMFXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.24
• 重原子数：
  79
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,8-Bis-(tert-butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-1-[3-methyl-3-((S)-3-methyl-pentyl)-oxiranyl]-9H-carbazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以18%的产率得到epocarbazolin B
  参考文献：
  名称：

  First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (−)-epocarbazolin A via Shi epoxidation

  摘要：

  Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides a simple route to racemic epocarbazolin A and a non-diastereo selective access to epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of the non-natural (-)-epocarbazolin A. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.095
• 作为产物：
  描述：

  3,8-Bis-(tert-butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-((E)-(S)-2,5-dimethyl-hept-1-enyl)-2-methyl-9H-carbazole 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 以53%的产率得到3,8-Bis-(tert-butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-1-[3-methyl-3-((S)-3-methyl-pentyl)-oxiranyl]-9H-carbazole
  参考文献：
  名称：

  First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (−)-epocarbazolin A via Shi epoxidation

  摘要：

  Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides a simple route to racemic epocarbazolin A and a non-diastereo selective access to epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of the non-natural (-)-epocarbazolin A. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.095

文献信息

• First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (−)-epocarbazolin A via Shi epoxidation
  作者：Jan Knöll、Hans-Joachim Knölker

  DOI：10.1016/j.tetlet.2006.06.095

  日期：2006.8

  Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides a simple route to racemic epocarbazolin A and a non-diastereo selective access to epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of the non-natural (-)-epocarbazolin A. (c) 2006 Elsevier Ltd. All rights reserved.