tert-butyl 2-allyl-1H-indole-1-carboxylate | 919119-82-7

• 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: tert-butyl 2-allyl-1H-indole-1-carboxylate
• 英文别名: tert-Butyl 2-(prop-2-en-1-yl)-1H-indole-1-carboxylate；tert-butyl 2-prop-2-enylindole-1-carboxylate
• CAS: 919119-82-7
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: XDNUHFOXAHFXCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-allyl-1H-indole-1-carboxylate 在 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 、 TBS-DHG催化剂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 tert-butyl (R)-3-(2,3-dihydroxypropyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

  摘要：

  A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

  DOI：

  10.1021/jacs.7b12316
• 作为产物：
  描述：

  吲哚 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl 2-allyl-1H-indole-1-carboxylate
  参考文献：
  名称：

  Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

  摘要：

  A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

  DOI：

  10.1021/jacs.7b12316

文献信息

• Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins
  作者：Ryosuke Matsubara、Alicia C. Gutierrez、Timothy F. Jamison

  DOI：10.1021/ja209235d

  日期：2011.11.30

  Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including

  描述了镍催化的未活化烯烃的分子间苄基化和杂苄基化，以提供功能化的烯丙基苯衍生物。广泛的苄基氯和烯烃偶联伙伴都是可以容忍的。与该过程的类似钯催化变体相比，本文所述的所有反应均使用电子无偏脂肪族烯烃（包括乙烯），在室温下进行，并提供 1,1-二取代烯烃而不是更常见的 1,2-二取代烯烃具有非常高的选择性。
• Aerobic Asymmetric Allylic C−H Alkylation by Synergistic Chiral Primary Amine‐Palladium‐Hydroquinone Catalysis
  作者：Rui Wang、Long Zhang、Sanzhong Luo

  DOI：10.1002/chem.202304316

  日期：2024.3.15

  A ternary and synergistic chiral primary amine/palladium /p-hydroquinone catalysis was developed to facilitate oxidative asymmetric allylic C−H alkylation under aerobic conditions with high regio- and enantioselectivity.

  开发了三元协同手性伯胺/钯/对氢醌催化，以促进有氧条件下的氧化不对称烯丙基 C−H 烷基化，具有高区域和对映选择性。
• Regioselective Reaction of 2-Indolylcyanocuprates with Electrophiles
  作者：Minoru Ishikura、Reina Uemura、Koji Yamada、Reiko Yanada

  DOI：10.3987/com-06-10865

  日期：——

  The reaction of 2-indolylcyanocuprate with electrophiles was found to give rise to 2- and 3-substituted indoles in regioselective manner.
• Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope
  作者：Lu Yan、Yan Meng、Fredrik Haeffner、Robert M. Leon、Michael P. Crockett、James P. Morken

  DOI：10.1021/jacs.7b12316

  日期：2018.3.14

  A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.