(E)-1-(1H-indol-1-yl)-3-phenylprop-2-en-1-one | 201486-55-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(1H-indol-1-yl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-N-(3-phenylacryloyl)indole；N-cinnamoylindole；(E)-1-indol-1-yl-3-phenylprop-2-en-1-one
• CAS: 201486-55-7
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: TZESEVOODDUWFL-ZHACJKMWSA-N

物化性质

• 熔点：
  104.1-105.2 °C
• 沸点：
  338.2±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(1H-indol-1-yl)-3-phenylprop-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.42h， 以85%的产率得到反式肉桂醛
  参考文献：
  名称：

  2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acids.

  摘要：

  The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10491-9
• 作为产物：
  描述：

  2-(2,2-二甲氧基乙基)苯甲酰胺 在 吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 1.67h， 生成 (E)-1-(1H-indol-1-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acids.

  摘要：

  The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10491-9

文献信息

• Oxidative organocatalytic chemoselective <i>N</i>-acylation of heterocycles with aromatic and conjugated aldehydes
  作者：Linda Ta、Henrik Sundén

  DOI：10.1039/c7cc08672e

  日期：——

  reactive acyl chloride derivatives or coupling reagents. Here we report a mild, functional group tolerant and highly chemoselective oxidative carbene catalyzed N-acylation of indoles with aldehydes. The acylation has a broad substrate scope and is compatible with substituents on both the aldehyde and the indole reaction partner. Furthermore, aza-heterocycles such as pyrrole and indazole can also be used

  吲哚的选择性酰化繁琐，通常涉及对敏感和反应性酰氯衍生物或偶联剂的需求。在这里，我们报告温和的，官能团耐受和高度化学选择性氧化卡宾催化醛与吲哚的N-酰化。酰化具有广泛的底物范围，并且与醛和吲哚反应配偶体上的取代基相容。此外，氮杂杂环如吡咯和吲唑也可以用作该反应中的亲核试剂，以高收率提供相应的酰胺同类物。
• Dinuclear Zinc Catalyzed Asymmetric Spirannulation Reaction: An Umpolung Strategy for Formation of α-Alkylated-α-Hydroxyoxindoles
  作者：Barry M. Trost、Keiichi Hirano

  DOI：10.1021/ol300577y

  日期：2012.5.18

  A highly diastereo- and enantioselective formal [3 + 2] cycloaddition of α,β-unsaturated esters and 3-hydroxyoxindoles catalyzed by a dinuclear zinc-ProPhenol complex is reported. The stereoselective Michael additions of 3-hydroxyoxindoles and the subsequent transesterifications afford spirocyclic δ-lactones.

  据报道，由双核锌-ProPhenol配合物催化的α，β-不饱和酯和3-羟基羟吲哚的高度非对映体和对映体选择性的[3 + 2]环加成反应。3-羟基羟吲哚的立体选择性迈克尔加成和随后的酯交换反应提供螺环δ-内酯。
• One-Pot Michael Addition/Radical Cyclization Reaction of N-Acryloyl Indoles
  作者：Lauren Irwin、Michael Kerr

  DOI：10.1055/s-0036-1589105

  日期：2017.12

  From N -acryloyl indoles, ten examples of 1,2-annulated ­indole products were generated in a one-pot procedure via a Michael addition and radical cyclization mediated by Mn(OAc) 3 .

  从 N-丙烯酰基吲哚中，通过迈克尔加成和由 Mn(OAc) 3 介导的自由基环化，在一锅法中生成了 1,2-环化吲哚产物的 10 个实例。
• 一种N-酰基吲哚手性硼化合物的合成方法
  申请人：中国科学院大连化学物理研究所

  公开号：CN108148084A

  公开（公告）日：2018-06-12

  本发明公开了一种具有潜在生物活性的N‑酰基吲哚手性硼化合物的合成方法。以α,β‑不饱和N‑酰基吲哚与双联频哪醇基二硼烷为原料，手性配体铜盐为催化剂，进行不对称硼化反应合成手性硼化合物。与已报道合成手性硼化合物的方法相比较，本发明原料易得、操作简便、适用范围广以及反应条件温和，产物中含有吲哚取代基，具有潜在的生物活性。
• α,β-Unsaturated <i>N</i>-Acylindoles: An Alternative Class of Michael Acceptors and Their Application in Asymmetric Borylation
  作者：Quanbin Jiang、Tenglong Guo、Runli Gao、Quannan Wang、Jiang Lou、Zhengkun Yu

  DOI：10.1021/acs.joc.8b00831

  日期：2018.8.3

  Copper(I)-catalyzed enantioselective borylation of alpha,beta-unsaturated N-acylindoles as well as N-acylpyrroles was efficiently achieved by means of bis(pinacolato)diboron (B(2)pin(2)), affording the enantioenriched products in excellent yields with up to 99% ee. The present work provides an alternative class of Michael acceptors, that is, alpha,beta-unsaturated N-acylindoles, for potential asymmetric transformations.