(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester | 176685-39-5

• 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: (S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester
• 英文别名: 6-O-tert-butyl 1-O-methyl (8S)-8-(acetyloxymethyl)-4-phenylmethoxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate
• CAS: 176685-39-5
• 化学式: C₂₇H₃₀N₂O₇
• 分子量: 494.544
• InChiKey: UXDHFHMDTKMUCJ-SFHVURJKSA-N

物化性质

• 沸点：
  634.0±55.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester 在 四氯化碳 、 dimethyl sulfide borane 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Novel Syntheses of Optically Active CC-1065, U-73,975(Adozelesin), U-80,244(Carzelesin), U-77,779 (Bizelesin), KW-2189, and DU-86

  摘要：

  The title syntheses were achieved by the method featuring oxidative cyclization of the enamino esters [(S)-13 and (S)-24] derived from the 5-aminoindoline [(S)-12], acylation with various structural types of indole-2-carboxylic acids, and formation of cyclopropapyrroloindole moieties.

  DOI：

  10.3987/com-97-7920
• 作为产物：
  描述：

  (S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 在 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以23%的产率得到(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester
  参考文献：
  名称：

  Novel Syntheses of Optically Active CC-1065, U-73,975(Adozelesin), U-80,244(Carzelesin), U-77,779 (Bizelesin), KW-2189, and DU-86

  摘要：

  The title syntheses were achieved by the method featuring oxidative cyclization of the enamino esters [(S)-13 and (S)-24] derived from the 5-aminoindoline [(S)-12], acylation with various structural types of indole-2-carboxylic acids, and formation of cyclopropapyrroloindole moieties.

  DOI：

  10.3987/com-97-7920

文献信息

• Synthesis and Cytotoxicity of Various Structural Types of Novel Cyclopropapyrroloindole(CPI) Derivatives
  作者：Yasumichi Fukuda、Hirosuke Furuta、Yoshie Kusama、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.3987/com-98-s21

  日期：——

  The various structural types of novel cyclopropapyrroloindole(CPI) derivatives (7 similar to 10) were synthesized and their cytotoxicity was evaluated. Among these derivatives, 3-methoxycarbonylCPI(3-MCCPI) derivatives (8a,b) and cyclopropapyrrolocarbazole (CPC) derivative (10a) were found to exhibit comparable cytotoxicity to U-73,975 (adozelesin) (1).