3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester | 226888-27-3

• 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-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester
• 英文别名: ethyl (E)-3-(6-bromo-1H-indol-3-yl)prop-2-enoate
• CAS: 226888-27-3
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: HIJUFBCNTPCBJJ-ZZXKWVIFSA-N

物化性质

• 沸点：
  444.8±30.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester 在 Lindlar's catalyst bismuth(III) chloride 、 氢氧化钾 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 二苯基磷酸 、 氢气 、 sodium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.25h， 生成 3-(6-<5-<(2-tert-butoxycarbonylamino-acetylamino)methyl>-2,3-dimethoxyphenyl>-3H-indol-3-yl)-propionic acid
  参考文献：
  名称：

  Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin

  摘要：

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00171-4
• 作为产物：
  描述：

  6-溴吲哚-3-甲醛 、 丙二酸单乙酯 在 哌啶 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以97%的产率得到3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin

  摘要：

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00171-4

文献信息

• 10.1039/d4ob00861h
  作者：Chauhan, Amar Nath Singh、Vini, Vikrant、Kumar, Akhilesh、Erande, Rohan D.

  DOI：10.1039/d4ob00861h

  日期：——

  An efficient Cu(OTf)2-catalyzed [3 + 2] cycloaddition of indole-3-acrylate with p-benzoquinone has been developed to construct two distinct indole-tethered benzofuran scaffolds, offering the first-ever selective access to these scaffolds. Moreover, the [4 + 2] cycloaddition reaction of indole-3-acrylate with vinyl ketone derivatives was used to synthesize carbazoles in a one-pot manner. The disclosed

  已开发出一种有效的 Cu(OTf) 2催化的 3-丙烯酸吲哚与对苯醌的 [3 + 2] 环加成反应，用于构建两种不同的吲哚系苯并呋喃支架，首次选择性地获得这些支架。此外，利用3-吲哚丙烯酸酯与乙烯基酮衍生物的[4+2]环加成反应，一锅法合成咔唑类化合物。所公开的策略提供了在低催化剂负载下的一系列选择性转化，具有广泛的底物范围，其特点是所开发的方案具有多种适用性和实际简单性，且底物容易获得。
• Composite MALDI matrix material and methods of using it and kits thereof in MALDI
  申请人：Sze Newman Siu Kwan

  公开号：US20060261267A1

  公开（公告）日：2006-11-23

  The present invention relates to a composite matrix material for Matrix-assisted Laser Desorption/Ionisation (MALDI), a process for preparing the same, and a method of its use in MALDI. The invention also relates to a kit for carrying out MALDI. The matrix material comprises at least one MALDI matrix forming compound and a polymer. The polymer serves as supporting material for the at least one MALDI matrix forming compound to which it is covalently linked.
• [EN] COMPOSITE MALDI MATRIX MATERIAL AND METHODS OF USING IT AND KITS THEREOF IN MALDI<br/>[FR] MATÉRIAU COMPOSITE À MATRICE MALDI ET SES PROCÉDÉS D'UTILISATION ET ENSEMBLES PRÉFABRIQUÉS CORRESPONDANTS POUR MALDI
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2006124003A1

  公开（公告）日：2006-11-23

  [EN] The present invention relates to a composite matrix material for Matrix-assisted Laser Desorption/Ionisation (MALDI), a process for preparing the same, and a method of its use in MALDI. The invention also relates to a kit for carrying out MALDI. The matrix material comprises at least one MALDI matrix forming compound and a polymer. The polymer serves as supporting material for the at least one MALDI matrix forming compound to which it is covalently linked.
  [FR] La présente invention concerne un matériau composite matriciel pour désorption/ionisation laser assistée par matrice (MALDI), un procédé pour le préparer, et un procédé pour son utilisation en MALDI. La présente invention concerne également un ensemble préfabriqué pour réaliser la MALDI. Le matériau matriciel comprend au moins un composant de formation de matrice MALDI et un polymère. Le polymère sert de matériau de support pour le au moins un composant de formation de matrice MALDI auquel il est lié de façon covalente.
• Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin
  作者：René Beugelmans、Georges Roussi、Eduardo González Zamora、Annie-Claude Carbonnelle

  DOI：10.1016/s0040-4020(99)00171-4

  日期：1999.4

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.