arsindoline B | 1234202-25-5

• 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: arsindoline B
• 英文别名: 2,2-bis(1H-indol-3-yl)ethyl butanoate
• CAS: 1234202-25-5
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: AWZODBRCMWCKSF-UHFFFAOYSA-N

物化性质

• 沸点：
  580.1±40.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  双(7-溴-1H-吲哚-3-基)乙酸 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 硫酸 、 三正丁基氢锡 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 49.0h， 生成 arsindoline B
  参考文献：
  名称：

  One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis

  摘要：

  A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.

  DOI：

  10.1021/ol401486s

文献信息

• One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles
  作者：Jiachen Xiang、Jungang Wang、Miao Wang、Xianggao Meng、Anxin Wu

  DOI：10.1039/c5ob00025d

  日期：——

  This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products.

  本文描述了氨基酸与吲哚的脱羧脱氨双偶联反应，形成BIM骨架，并进一步应用于天然产物的一锅式全合成。
• Synthesis of indole alkaloids arsindoline A, arsindoline B and their analogues in low melting mixture
  作者：Rama Raju Jella、Rajagopal Nagarajan

  DOI：10.1016/j.tet.2013.10.037

  日期：2013.12

  Synthesis of newly isolated bis(indolyl)methane alkaloids arsindoline A, arsindoline B from a marine-derived bacterium strain CB101 and their analogues are reported using low melting L-(+)-tartaric acid dimethyl urea mixture. The reaction is mild, non-toxic, and occurs in environmentally benign conditions. We also reported the synthesis of another alkaloid 2,2-bis(6-bromo-1H-indol-3-yl)ethanamine using low melting mixture. (C) 2013 Elsevier Ltd. All rights reserved.
• One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis
  作者：Takumi Abe、Shuuhei Nakamura、Reiko Yanada、Tominari Choshi、Satoshi Hibino、Minoru Ishikura

  DOI：10.1021/ol401486s

  日期：2013.7.19

  A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.