ethyl 7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate | 71948-60-2

• 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 7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate
• 英文别名: ethyl 6-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-4-carboxylate
• CAS: 71948-60-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: AVBXQNXQKCZZBV-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  419.3±33.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 6-hydroxyhex-2-ynoate 在 草酰氯 、 氧气 、 palladium diacetate 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 ethyl 7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate
  参考文献：
  名称：

  Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles

  摘要：

  Heating a DMA/pivalic acid (v/v=4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)(2) under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C-H activation and reductive elimination was proposed to account for the observed bis-cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.003

文献信息

• Synthesis of Indoles via Domino Reaction of <i>N</i>-Aryl Amides and Ethyl Diazoacetate
  作者：Sun-Liang Cui、Jing Wang、Yan-Guang Wang

  DOI：10.1021/ja805706r

  日期：2008.10.15

  A general and concise synthesis of functionalized indoles via domino reaction of N-aryl amides and ethyl diazoacetate has been developed. The methodology offers a great potential for the synthesis of biologically active and naturally occurring indole derivatives.

  已经开发了通过 N-芳基酰胺和重氮乙酸乙酯的多米诺反应来合成功能化吲哚的通用而简洁的方法。该方法为合成具有生物活性和天然存在的吲哚衍生物提供了巨大的潜力。
• Synthesis of pyrrolo[1,2-a]indoles by intramolecular heck reaction of N-(2-bromoaryl) enaminones
  作者：Joseph P. Michael、Shih-Fang Chang、Clare Wilson

  DOI：10.1016/s0040-4039(00)61432-6

  日期：1993.12

  Treatment of N-(2-bromoaryl) enaminones 4, prepared by several different methods, with palladium (II) acetate, triarylphosphine and triethylamine in boiling acetonitrile gave pyrrolo[1,2-a]indoles 8 yields of 50% – 100%. The hydroxy-substituted products 8k could be oxidised to the mitosene-like quinone 9 with Fremy's salt.

  用几种不同方法制备的N-（2-溴芳基）烯胺酮4在沸腾的乙腈中用乙酸钯（II），三芳基膦和三乙胺处理，得到吡咯并[1,2- a ]吲哚8的收率为50％-100％。羟基取代的产物8k可以用弗雷米氏盐氧化成类似米托烯的醌9。
• Electron Donor–Acceptor Complex Induced Fused Indoles with Hypervalent Iodine(III) Reagents
  作者：Li Liu、Yage Zhang、Wenyan Zhao、Jian Li

  DOI：10.1021/acs.orglett.3c02009

  日期：2023.9.1

  An operationally simple and efficient method for the cyclization of tertiary amines and hypervalent iodine reagents enabled by an EDA complex has been developed. A series of [1,2-α]indoles derivatives were obtained in good yields, including some key intermediates for the synthesis of biologically active molecules. In addition, this established strategy features a broad substrate scope and good functional

  已经开发出一种操作简单且有效的通过 EDA 复合物实现叔胺和高价碘试剂环化的方法。以良好的收率获得了一系列[1,2-α]吲哚衍生物，其中包括一些用于合成生物活性分子的关键中间体。此外，该既定策略具有广泛的底物范围和良好的官能团耐受性。
• CN116462683
  申请人：——

  公开号：——

  公开（公告）日：——
• Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles
  作者：Tiffany Piou、Luc Neuville、Jieping Zhu

  DOI：10.1016/j.tet.2013.01.003

  日期：2013.6

  Heating a DMA/pivalic acid (v/v=4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)(2) under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C-H activation and reductive elimination was proposed to account for the observed bis-cyclization. (C) 2013 Elsevier Ltd. All rights reserved.