1-methyl-2-(N-benzyloxycarbonylindolin-2-yl)ethanone | 1361525-14-5

• 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: 1-methyl-2-(N-benzyloxycarbonylindolin-2-yl)ethanone
• 英文别名: (2R)-N-benzyloxycarbonyl-2-(2-oxopropyl)indoline；benzyl (2R)-2-(2-oxopropyl)-2,3-dihydroindole-1-carboxylate
• CAS: 1361525-14-5
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: JBBKBWONZHPDBG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl (2-allylphenyl)carbamate 在 (6-甲氧基-4-喹啉基)-(5-乙烯基奎宁环-2-基)甲胺 、 Hoveyda-Grubbs catalyst second generation 、 五氟丙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 32.0h， 生成 1-methyl-2-(N-benzyloxycarbonylindolin-2-yl)ethanone
  参考文献：
  名称：

  Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones

  摘要：

  AbstractAn organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐epi‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.

  DOI：

  10.1002/chem.201101292

文献信息

• Enantioselective synthesis of 2-substituted pyrrolidinesvia domino cross metathesis/intramolecular aza-Michael addition
  作者：Hanbin Liu、Chuanqi Zeng、Jiajia Guo、Mengyao Zhang、Shouyun Yu

  DOI：10.1039/c2ra22374k

  日期：——

  intramolecular aza-Michael addition with enone carbamates catalyzed by chiral Brønsted acids was developed. A domino cross metathesis/aza-Michael addition for the preparation of 2-substituted pyrrolidines or benzopyrrolidines was also explored. The reactions described here provide an efficient asymmetric protocol for enantio-enriched heterocycles, especially 2-substituted pyrrolidines.

  开发了一种高度对映选择性的分子内氮杂-迈克尔加成化合物，该化合物具有手性布朗斯台德酸催化的烯酮氨基甲酸酯。还研究了用于制备2-取代的吡咯烷或苯并吡咯烷的多米诺交叉复分解/氮杂-迈克尔加成反应。本文所述的反应为富含对映体的杂环，尤其是2-取代的吡咯烷酮提供了有效的不对称方案。
• Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts
  作者：Ryota Miyaji、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol401538b

  日期：2013.7.19

  A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The catalytic process was shown to be highly versatile and applicable to a wide range of substrates due to the flexible catalytic mechanism utilizing a noncovalent interaction.