lithium triethyl(1-tert-butoxycarbonylindol-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-tert-butoxycarbonylindol-2-yl)borate
• 英文别名: Lithium;triethyl-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boranuide
• 化学式: C₁₉H₂₉BNO₂*Li
• 分子量: 321.197
• InChiKey: HABCSVVTCLUVMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lithium triethyl(1-tert-butoxycarbonylindol-2-yl)borate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 phenylmethyl 6-[(tert-butyl)oxycarbonyl]-5,11-dimethyl-1,2,3,4-tetrahydropyrido[4,3-b]carbazole-2-carboxylate
  参考文献：
  名称：

  玫瑰树碱的高效全合成

  摘要：

  A total synthesis of ellipticine could be attained through the palladium catalyzed tandem cyclization-cross-coupling reaction of indolylborate (2 b) with vinyl bromide (3) as a key reaction.

  DOI：

  10.3987/com-99-8759
• 作为产物：
  描述：

  三乙基硼 、 1-Boc-吲哚 以 四氢呋喃 、 正戊烷 、 正己烷 为溶剂， 反应 4.0h， 生成 lithium triethyl(1-tert-butoxycarbonylindol-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。
• Synthesis and cytotoxicity of pyrido[4,3-b]carbazole alkaloids against HCT-116 and HL-60 cells
  作者：Tomoki Itoh、Noriyuki Hatae、Takashi Nishiyama、Tominari Choshi、Satoshi Hibino、Teruki Yoshimura、Minoru Ishikura

  DOI：10.1007/s00044-017-2068-6

  日期：2018.2

  known about the biological activities of these compounds. Six synthetic natural alkaloids and five of their derivatives were evaluated for their antiproliferative activity against HCT-116 and HL-60 cells. The activities of variants with the D-reduced ring or without the C(11)-Me group were lower than those of ellipticine. The conformer of guatambuine showed higher activities than guatambuine.

  通过钯催化的串联环化/交叉偶联反应作为关键步骤，合成了玫瑰树碱，奥利福因及其五个还原的天然变异体。另外，通过在茉莉花碱中D环的构象转化获得了先前未知的茉莉花碱构象物。由于几乎没有用于减少天然变异体的合成方法，因此对这些化合物的生物学活性知之甚少。评价了六种合成天然生物碱及其五种衍生物对HCT-116和HL-60细胞的抗增殖活性。具有D还原环或没有C（11）-Me组的变体的活性低于玫瑰树碱。guatambuine的构象异构体显示出比guatambuine高的活性。
• 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.
• Application of the Pd-catalyzed heteroarylation to the synthesis of 5-(indol-2′-yl)pyridin-2-one and 5-(indol-2′-yl)pyran-2-one
  作者：Bruno Danieli、Giordano Lesma、Marisa Martinelli、Daniele Passarella、Ilaria Peretto、Alessandra Silvani

  DOI：10.1016/s0040-4020(98)00858-8

  日期：1998.11

  The synthesis of 5-(indol-2'-yl)pyridin-2-ones and 5-(indol-2'-yl)pyran-2-one by Pd-catalyzed reactions is described. The best results are obtained using 2-indolylstannanes or 2-indolylzinc halides to be coupled with 5-bromopyridin-2-ones or 5-bromopyran-2-one in the presence of Pd(PPh3)(4) catalyst. Other Pd-catalyzed reactions are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.