ethyl (E)-3-(2-methyl-1H-indol-3-yl)acrylate | 29266-16-8

• 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: ethyl (E)-3-(2-methyl-1H-indol-3-yl)acrylate
• 英文别名: 3-(2-Methyl-1H-indol-3-YL)-acrylic acid ethyl ester；ethyl (E)-3-(2-methyl-1H-indol-3-yl)prop-2-enoate
• CAS: 29266-16-8
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: YCWFVSKTQYNIFA-CMDGGOBGSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  399.3±27.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  ethyl (E)-3-(2-methyl-1H-indol-3-yl)acrylate 在 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以62%的产率得到(Z)-ethyl 2-bromo-3-(2-methyl-1H-indol-3-yl)propenoate
  参考文献：
  名称：

  （S，Z）-3-[（1 H-吲哚-3-基）亚甲基]六氢吡咯并[1,2- a ]吡嗪-4（1 H）-的合成：一种基于烯胺酮的不饱和路线环二肽

  摘要：

  一系列外消旋和对映体纯的（S，Z）-3-[（1 H-吲哚-3-基）亚甲基]六氢吡咯并[1,2- a ]吡嗪-4（1 H）-一个（环Pro–ΔTrp）制备了二肽类似物。外消旋类似物6a – c是通过将外消旋环二肽烯胺酮（R，S）-5与各种吲哚衍生物直接偶联制备的。另一方面，通过铜（I）催化的乙烯基酰胺化反应制备了对映纯类似物，其中无环（S）-Pro-ΔTrp二肽类似物20和21形成了。无环二肽被环化为对映体（S）-Pro-ΔTrp二肽类似物24和25。对于偶联反应，分几个步骤制备乙烯基溴。由乙酸乙酯（7）制备烯胺酮8，并与2-甲基吲哚和2-苯基吲哚偶联，得到9和10。3-（吲哚-3-基）丙烯酸酯9和10在位置2上的直接溴化反应生成乙烯基溴化物11和12。乙烯基溴化物11和12中吲哚氮1'上的Boc保护基在进行铜（I）与N- Boc脯氨酰胺18的偶合之前，先引入苯乙二胺。手性中间体和终产物的对映体纯度主要通过HPLC或1

  DOI：

  10.1016/j.tet.2008.01.045
• 作为产物：
  描述：

  2-甲基吲哚 、 丙炔酸乙酯 在 iron(III) chloride 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 反应 36.0h， 以98%的产率得到ethyl (E)-3-(2-methyl-1H-indol-3-yl)acrylate
  参考文献：
  名称：

  Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles

  摘要：

  Intermolecular hydroarylation of propynoic acid and its esters with indoles proceeded efficiently in acetic acid under a catalytic system of FeCl3/3AgOTf and afforded the corresponding 3,3-bis(indol-3yl) propanoic acids and their esters in high yields. In the case of 2-methylindole, 3-indolylacrylic acid and its ethyl ester were obtained in high yields. This iron-catalyzed hydroarylation showed a high regioselectivity at the 3-position of indoles and a high utility for the synthesis of bis(indol-3-yl) compounds, which are important for biological and pharmaceutical fields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.051

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。
• Aerobic C–H Olefination of Indoles via a Cross-Dehydrogenative Coupling in Continuous Flow
  作者：Hannes P. L. Gemoets、Volker Hessel、Timothy Noël

  DOI：10.1021/ol502910e

  日期：2014.11.7

  Herein, we report the first site-selective, Pd(II)-catalyzed, cross-dehydrogenative Heck reaction of indoles in micro flow. By use of a capillary microreactor, we were able to boost the intrinsic kinetics to accelerate former hour-scale reaction conditions in batch to the minute range in flow. The synergistic use of microreactor technology and oxygen, as both terminal oxidant and mixing motif, highlights the sustainable aspect of this process.
• Synthesis of (S,Z)-3-[(1H-indol-3-yl)methylidene]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one: an alternative, enaminone based, route to unsaturated cyclodipeptides
  作者：Jernej Wagger、Uroš Grošelj、Anton Meden、Jurij Svete、Branko Stanovnik

  DOI：10.1016/j.tet.2008.01.045

  日期：2008.3

  A series of racemic and enantiopure (S,Z)-3-[(1H-indol-3-yl)methylidene]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one (cyclic Pro–ΔTrp) dipeptide analogues were prepared. Racemic analogues 6a–c were prepared by direct coupling of racemic cyclodipeptide enaminone (R,S)-5 with various indole derivatives. On the other hand, enantiopure analogues were prepared through a copper(I) catalyzed vinyl amidation reaction

  一系列外消旋和对映体纯的（S，Z）-3-[（1 H-吲哚-3-基）亚甲基]六氢吡咯并[1,2- a ]吡嗪-4（1 H）-一个（环Pro–ΔTrp）制备了二肽类似物。外消旋类似物6a – c是通过将外消旋环二肽烯胺酮（R，S）-5与各种吲哚衍生物直接偶联制备的。另一方面，通过铜（I）催化的乙烯基酰胺化反应制备了对映纯类似物，其中无环（S）-Pro-ΔTrp二肽类似物20和21形成了。无环二肽被环化为对映体（S）-Pro-ΔTrp二肽类似物24和25。对于偶联反应，分几个步骤制备乙烯基溴。由乙酸乙酯（7）制备烯胺酮8，并与2-甲基吲哚和2-苯基吲哚偶联，得到9和10。3-（吲哚-3-基）丙烯酸酯9和10在位置2上的直接溴化反应生成乙烯基溴化物11和12。乙烯基溴化物11和12中吲哚氮1'上的Boc保护基在进行铜（I）与N- Boc脯氨酰胺18的偶合之前，先引入苯乙二胺。手性中间体和终产物的对映体纯度主要通过HPLC或1
• Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles
  作者：Md. Shahajahan Kutubi、Tsugio Kitamura

  DOI：10.1016/j.tet.2011.08.051

  日期：2011.10

  Intermolecular hydroarylation of propynoic acid and its esters with indoles proceeded efficiently in acetic acid under a catalytic system of FeCl3/3AgOTf and afforded the corresponding 3,3-bis(indol-3yl) propanoic acids and their esters in high yields. In the case of 2-methylindole, 3-indolylacrylic acid and its ethyl ester were obtained in high yields. This iron-catalyzed hydroarylation showed a high regioselectivity at the 3-position of indoles and a high utility for the synthesis of bis(indol-3-yl) compounds, which are important for biological and pharmaceutical fields. (C) 2011 Elsevier Ltd. All rights reserved.