3-(7-chloro-1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione | 221377-34-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-(7-chloro-1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione
• 英文别名: 3-[7-chloro-1-[(2R,3R,4R,5R,6R)-3-hydroxy-5-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]indol-3-yl]-4-(7-chloro-1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 221377-34-0
• 化学式: C₄₁H₃₅Cl₂N₃O₇
• 分子量: 752.651
• InChiKey: KMDLHQKHESWMLF-HUEXKYJKSA-N

物化性质

• 沸点：
  956.4±65.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(7-chloro-1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione 在 Pd(OTf)₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以66%的产率得到1,11-dichloro-12,13-dihydro-12-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-5H-indolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis of Rebeccamycin and 11-Dechlororebeccamycin

  摘要：

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.

  DOI：

  10.1021/jo982277b
• 作为产物：
  描述：

  7-氯吲哚 在 氢氧化钾 、 potassium tert-butylate 、 sodium hydride 、 乙酸乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 31.0h， 生成 3-(7-chloro-1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of Rebeccamycin and 11-Dechlororebeccamycin

  摘要：

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.

  DOI：

  10.1021/jo982277b

文献信息

• Synthesis of Rebeccamycin and 11-Dechlororebeccamycin
  作者：Margaret M. Faul、Leonard L. Winneroski、Christine A. Krumrich

  DOI：10.1021/jo982277b

  日期：1999.4.1

  Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.