(Z)-3-[2-(1H-Indol-3-yl)-ethylamino]-but-2-enoic acid ethyl ester | 604763-32-8

• 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: (Z)-3-[2-(1H-Indol-3-yl)-ethylamino]-but-2-enoic acid ethyl ester
• 英文别名: ethyl (Z)-3-[2-(1H-indol-3-yl)ethylamino]but-2-enoate
• CAS: 604763-32-8
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: SZBQAYCADFBCFE-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-[2-(1H-Indol-3-yl)-ethylamino]-but-2-enoic acid ethyl ester 在 camphor-10-sulfonic acid 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 1.0h， 生成 (1R,2R,11bS)-2-Carboxymethyl-2,11b-dimethyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization

  摘要：

  Enaminoesters containing a tethered indole or aryl moiety on the amine react with substituted maleic anhydrides or acryloyl chlorides to provide pyrrolinone or dihydropyridone products, respectively. The indole-tethered dihydropyridones can be induced to undergo a one-pot cyclization whereas, the indole-tethered pyrrolinone intermediates are readily cyclized with HCl. The aryl-tethered pyrrolinones or dihydropyridones can be isolated and subsequently induced to cyclize with triflic acid. This methodology culminates in the synthesis of erythrane-like and other natural products that are readily amenable to combinatorial library production. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01190-0
• 作为产物：
  描述：

  色胺 、 2-丁炔酸乙酯 以 1,4-二氧六环 为溶剂， 反应 0.8h， 生成 (Z)-3-[2-(1H-Indol-3-yl)-ethylamino]-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  吲哚系四取代吡咯的铁催化一锅法合成及其对吲哚并[8,7-b]吲哚衍生物的转化

  摘要：

  我们开发了一种有效的铁催化色胺、炔酮和硝基烯烃的一锅反应，以可接受的良好收率提供吲哚系四取代吡咯。其他芳香族和脂肪族胺也可用于该过程，提供相应的高度官能化的四取代吡咯。Indolizino[8,7-b]indole 衍生物可以通过 TFA-、TfOH-或 Fe(OTf)3 介导的吲哚脱芳构化环化反应获得。当三甲基苯基三溴化铵 (PTAP) 用作亲电环化促进剂时，会形成意外的二溴化产物 7,9-二溴-6,11-二氢-5H-吲哚并[8,7-b] 吲哚。

  DOI：

  10.1055/a-1681-7480

文献信息

• An efficient chemo- and stereoselective synthesis of enaminones and enaminoesters using (bromodimethyl)sulfonium bromide under solvent-free conditions
  作者：Biswanath Das、Boddu Shashi Kanth、Anjoy Majhi、Kongara Ravinder Reddy

  DOI：10.1002/hc.20477

  日期：2008.9

  (Bromodimethyl)sulfonium bromide has efficiently been employed for chemo- and stereoselective conversions of β-dicarbonyl compounds into β-enaminones and β-enaminoesters by a treatment with amines at room temperature under solvent-free conditions. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:630–633, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20477

  （溴二甲基）溴化锍已有效地用于通过在室温下在无溶剂条件下用胺处理将 β-二羰基化合物化学和立体选择性转化为 β-烯胺酮和 β-烯胺酯。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:630–633, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20477
• Iron-Catalyzed One-Pot Synthesis of Indole-Tethered Tetrasubstituted Pyrroles and Their Transformations to Indolizino[8,7-b]indole Derivatives
  作者：Hai-Lei Cui、Xue Xiao、Xiao-Hui Chen、Xian-Xun Wang、Wan-Zhen Li

  DOI：10.1055/a-1681-7480

  日期：2022.4

  iron-catalyzed one-pot reaction of tryptamines, ynones and nitroolefins, affording indole-tethered tetrasubstituted pyrroles in acceptable to good yields. Other aromatic and aliphatic amines can also be utilized in this process, delivering the corresponding highly functionalized tetrasubstituted pyrroles. Indolizino[8,7-b]indole derivatives could be obtained through TFA-, TfOH- or Fe(OTf)3-mediated cyclizations

  我们开发了一种有效的铁催化色胺、炔酮和硝基烯烃的一锅反应，以可接受的良好收率提供吲哚系四取代吡咯。其他芳香族和脂肪族胺也可用于该过程，提供相应的高度官能化的四取代吡咯。Indolizino[8,7-b]indole 衍生物可以通过 TFA-、TfOH-或 Fe(OTf)3 介导的吲哚脱芳构化环化反应获得。当三甲基苯基三溴化铵 (PTAP) 用作亲电环化促进剂时，会形成意外的二溴化产物 7,9-二溴-6,11-二氢-5H-吲哚并[8,7-b] 吲哚。
• Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization
  作者：Matthew M Abelman、Jeffrey K Curtis、Donald R James

  DOI：10.1016/s0040-4039(03)01190-0

  日期：2003.8

  Enaminoesters containing a tethered indole or aryl moiety on the amine react with substituted maleic anhydrides or acryloyl chlorides to provide pyrrolinone or dihydropyridone products, respectively. The indole-tethered dihydropyridones can be induced to undergo a one-pot cyclization whereas, the indole-tethered pyrrolinone intermediates are readily cyclized with HCl. The aryl-tethered pyrrolinones or dihydropyridones can be isolated and subsequently induced to cyclize with triflic acid. This methodology culminates in the synthesis of erythrane-like and other natural products that are readily amenable to combinatorial library production. (C) 2003 Elsevier Ltd. All rights reserved.