(1,9-Dichloro-4-methylnon-5-yn-4-yl) methyl carbonate | 217465-43-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (1,9-Dichloro-4-methylnon-5-yn-4-yl) methyl carbonate
• CAS: 217465-43-5
• 化学式: C₁₂H₁₈Cl₂O₃
• 分子量: 281.179
• InChiKey: ZOKGVGLQURQGDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lithium triethyl(1-methylindol-2-yl)borate 、 (1,9-Dichloro-4-methylnon-5-yn-4-yl) methyl carbonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 0.5h， 生成 2-[6-chloro-1-(3-chloropropyl)-3-methylhexa-1,2-dienyl]-1-methylindole
  参考文献：
  名称：

  A concise access to 2-allenylindole derivatives based on the palladium catalyzed cross-coupling reaction of indolylborates

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(98)00861-8
• 作为产物：
  描述：

  5-氯-2-戊酮 、 5-氯戊炔 、 氯甲酸甲酯 在 正丁基锂 作用下， 以 正己烷 为溶剂， 生成 (1,9-Dichloro-4-methylnon-5-yn-4-yl) methyl carbonate
  参考文献：
  名称：

  A concise access to 2-allenylindole derivatives based on the palladium catalyzed cross-coupling reaction of indolylborates

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(98)00861-8

文献信息

• 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).