lithium triethyl(1-methylindol-2-yl)borate

• 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 triethyl(1-methylindol-2-yl)borate
• 英文别名: Lithium;triethyl-(1-methylindol-2-yl)boranuide
• 化学式: C₁₅H₂₃BN*Li
• 分子量: 235.106
• InChiKey: AYWFOSFTHRGBJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lithium triethyl(1-methylindol-2-yl)borate 在 二氯双(三邻甲苯膦)合钯(II) (n-Bu)4F 作用下， 以 四氢呋喃 为溶剂， 生成 3-Eth-(Z)-ylidene-4-[1-(1-methyl-1H-indol-2-yl)-meth-(Z)-ylidene]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies on the Preparation of 1,5-Methanoazocinoindole Based on Indolylborate

  摘要：

  Conversion of piperidine (8), readily available from the palladium catalyzed tandem cyclization-cross-coupling reaction of indolylborate (6) with bromide (7), to 1H-1,5-methanoazocino[4,3-b]indole (15) through piperidine (14) was investigated.

  DOI：

  10.3987/com-05-s(k)12
• 作为产物：
  描述：

  1-甲基吲哚 、 三乙基硼 以 四氢呋喃 、 正戊烷 、 正己烷 为溶剂， 反应 2.0h， 生成 lithium triethyl(1-methylindol-2-yl)borate
  参考文献：
  名称：

  N-取代的吲哚硼酸酯的反应研究：钯催化的交叉偶联反应和分子内烷基迁移反应

  摘要：

  研究了具有各种N-保护基的吲哚硼酸酯的钯催化的交叉偶联反应，其中发现N-甲基，N-甲氧基和N-叔丁氧基羰基是有用的。但是，（1-甲氧基甲基吲哚-2-基）硼酸三乙酯不能用于该反应。还发现三（1-甲氧基甲基吲哚-2-基）硼酸烷基酯的烷基迁移反应产生2-烷基-1-甲基吲哚，伴随着1-甲氧基甲基意外地还原为1-甲基。

  DOI：

  10.1002/jhet.5570360408

文献信息

• Investigation of the reaction of<i>N</i>-substituted indolylborates: Palladium catalyzed cross-coupling reactions and intramolecular alkyl migration reactions
  作者：Minoru Ishikura、Isao Agata、Nobuya Katagiri

  DOI：10.1002/jhet.5570360408

  日期：1999.7

  The palladium catalyzed cross-coupling reaction of indolylborates with various N-protecting groups was investigated, where N-Methyl, N-methoxy, and N-tert-butoxycarbonyl groups were found to be useful. However, triethyl(1-methoxymethylindol-2-yl)borate could not be used for this reaction. It was also found that the alkyl migration reaction of trialkyl(1-methoxymethylindol-2-yl)borate produced 2-alkyl-1-methyl-indole

  研究了具有各种N-保护基的吲哚硼酸酯的钯催化的交叉偶联反应，其中发现N-甲基，N-甲氧基和N-叔丁氧基羰基是有用的。但是，（1-甲氧基甲基吲哚-2-基）硼酸三乙酯不能用于该反应。还发现三（1-甲氧基甲基吲哚-2-基）硼酸烷基酯的烷基迁移反应产生2-烷基-1-甲基吲哚，伴随着1-甲氧基甲基意外地还原为1-甲基。
• Palladium-catalysed tandem cyclisation–cross-coupling reaction with triethyl-(1-methylindol-2-yl)borate
  作者：Minoru Ishikura

  DOI：10.1039/c39950000409

  日期：——

  Triethyl(1-methylindol-2-yl)borate 1 is successfully applied for the palladium-catalysed tandem cyclisation–cross-coupling reaction, which is used for a concise access to ellipticine derivatives.

  （1-甲基吲哚-2-基）硼酸三乙酯1已成功用于钯催化的串联环化-交叉偶联反应，该反应可用于简化玫瑰树碱衍生物的制备。
• A concise access to 2-allenylindole derivatives based on the palladium catalyzed cross-coupling reaction of indolylborates
  作者：Minoru Ishikura、Yukinori Matsuzaki、Isao Agata、Nobuya Katagiri

  DOI：10.1016/s0040-4020(98)00861-8

  日期：1998.11

  The palladium catalyzed cross-coupling reaction of trialky](indol-2-yl)borates with prop-2-ynyl carbonates was developed for the preparation of 2-allenylindole derivatives. When the reaction of indolyl-borates with tert-prop-2-ynyl carbonates was carried out. 2-allenylindoles were obtained solely. Otherwise, indolylborates reacted with sec-prop-2-ynyl carbonates, giving rise to 2-allenylindoles and/or 3-(prop-2-ynyl)indoles depending on the catalyst used. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Concise Preparation of Yuehchukene and Its Analogues
  作者：Minoru Ishikura、Katsuaki Imaizumi、Nobuya Katagiri

  DOI：10.3987/com-00-9008

  日期：——

  The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.
• Palladium Catalyzed Carbonylative Cross-Coupling Reaction of Indolylborates with Prop-2-ynyl Carbonates
  作者：Minoru Ishikura、Harue Uchiyama、Noriyuki Matsuzaki

  DOI：10.3987/com-01-9188

  日期：——

  Palladium catalyzed carbonylative cross-coupling reaction of 1-methylindolylborate (20) with prop-2-ynyl carbonates (3) produced cyclopenta[b]indole derivatives in a one-pot manner. Hence, the use of indolylborates (2c, d) for the reaction with 3 allowed the isolation of indol-2-yl allenyl ketones (4).