lithium 2-(lithiomethyl)indole-1-carboxylate

• 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: lithium 2-(lithiomethyl)indole-1-carboxylate
• 化学式: C₁₀H₇LiNO₂*Li
• 分子量: 187.053
• InChiKey: SJMJZLDLNGGQOE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.46
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lithium 2-(lithiomethyl)indole-1-carboxylate 以 四氢呋喃 、 正戊烷 为溶剂， 反应 13.0h， 生成 2-(1H-indol-2-yl)-1,1-diphenylethanol
  参考文献：
  名称：

  Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. V. Activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution

  摘要：

  DOI：

  10.1021/ja00281a061
• 作为产物：
  描述：

  2-甲基吲哚 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 生成 lithium 2-(lithiomethyl)indole-1-carboxylate
  参考文献：
  名称：

  Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. V. Activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution

  摘要：

  DOI：

  10.1021/ja00281a061

文献信息

• Benzoannelation of 2-methylindole via 1-N-carboxy-2-methylindole dianion: A direct regiospecific route to substituted and annelated carbazoles
  作者：U.K.Syam Kumar、Pranab K. Patra、H. Ila、H. Junjappa

  DOI：10.1016/s0040-4039(98)00164-6

  日期：1998.4

  A facile general route for substituted and annelated N-H-carbazoles 6 has been developed by regiospecific 1,2-addition of 1-N-carboxy-2-methylindole dianion 3 to acyclic and cyclic α-oxoketene dithioacetals 4 followed by cycloaromatization in the presence of H3PO4.

  通过将1-N-羧基-2-甲基吲哚阴离子3的区域特异性1，2-加成到无环和环状的α-氧杂环丁烯二硫缩醛4上，然后在存在下进行环芳构化，已经开发出一种容易的取代和退火的NH-咔唑6的通用路线。 H 3 PO 4。
• Salas, Marisa; Joule, John A., Journal of Chemical Research, Miniprint, 1990, # 3, p. 664 - 673
  作者：Salas, Marisa、Joule, John A.

  DOI：——

  日期：——
• Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids
  作者：Mercedes Amat、M.-Dolors Coll、Núria Llor、Carmen Escolano、Elies Molins、Carles Miravitlles、Joan Bosch

  DOI：10.1016/s0957-4166(03)00251-9

  日期：2003.6

  The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxyl ate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2-sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Enantiopure intermediates for the synthesis of Strychnos alkaloids
  作者：Mercedes Amat、Ma Dolors Coll、Joan Bosch

  DOI：10.1016/0040-4020(95)00641-k

  日期：1995.9

  The addition of 2-(lithiomethyl)indole 2 to the enantiopure oxazolinylpyridine 18 followed by acidic treatment afforded a mixture of tetracyclic compounds 21a and 21b in a 3:2 ratio. The major epimer 21a was converted to tetracycle 25a, a tetracyclic ABDE substructure of Strychnos alkaloids.