(E)-7-chloro-1-phenylhept-1-en-3-yne | 189116-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-7-chloro-1-phenylhept-1-en-3-yne
• 英文别名: (E)-(7-chlorohept-1-en-3-yn-1-yl)benzene；[(E)-7-chlorohept-1-en-3-ynyl]benzene
• CAS: 189116-17-4
• 化学式: C₁₃H₁₃Cl
• 分子量: 204.699
• InChiKey: AEQKLLNTKVGFKM-WEVVVXLNSA-N

物化性质

• 沸点：
  320.8±35.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-7-chloro-1-phenylhept-1-en-3-yne 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 32.0h， 生成 1-[2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]indol-3-yl]-N-tert-butylmethanimine
  参考文献：
  名称：

  Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes

  摘要：

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.

  DOI：

  10.1021/jo0343228
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 manganese (II) acetate tetrahydrate 、 二乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-7-chloro-1-phenylhept-1-en-3-yne
  参考文献：
  名称：

  钴催化 1,3-烯炔与 HBpin 选择性硼氢化反应生成 1,3-二烯基硼酸酯

  摘要：

  公开了一种有效的钴催化的1,3-烯炔与HBpin选择性硼氢化反应生成1,3-二烯基硼酸酯。使用市售的 Co(acac) 2和 dppf 催化体系，硼氢化反应进展顺利，以中等到高产率提供各种 1,3-二烯基硼酸酯。该方案具有廉价的贱金属催化系统、广泛的底物范围、优异的选择性、易于克级制备和良好的官能团耐受性，并提供了合成有价值的 1,3-二烯基硼酸盐。

  DOI：

  10.1021/acs.orglett.4c00899

文献信息

• An Efficient Synthesis of Stereodefined Enynes and Dienes via Pd-Catalyzed Reaction of Chloroenynes and Chlorodienes with Grignard Reagents
  作者：Parfait Ramiandrasoa、Bernard Bréhon、Armelle Thivet、Mouâd Alami*、Gérard Cahiez

  DOI：10.1016/s0040-4039(97)00365-1

  日期：1997.4

  In the presence of PdCl2(PPh(3))(2) and Et(3)N, chloroenynes and chlorodienes react rapidly under mild conditions with various Grignard reagents to give isomerically pure conjugated enynes, dienes, dienynes and trienes in good isolated yields. (C) 1997 Published by Elsevier Science Ltd.
• Synthesis of Annulated <i>γ</i>-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0343228

  日期：2003.6.1

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.
• Cobalt-Catalyzed Selective Hydroboration of 1,3-Enynes with HBpin toward 1,3-Dienylboronate Esters
  作者：Yining Jia、Liu Yang、Xueqiang Wang、Wen Yang、Wanxiang Zhao

  DOI：10.1021/acs.orglett.4c00899

  日期：2024.4.19

  cobalt-catalyzed selective hydroboration of 1,3-enynes with HBpin toward 1,3-dienylboronate esters is disclosed. With a commercially available catalytic system of Co(acac)2 and dppf, the hydroboration reactions proceeded well to afford a wide range of 1,3-dienylborates in moderate to high yields. This protocol features a cheap base-metal catalytic system, broad substrate scope, excellent selectivity, easy gram-scale

  公开了一种有效的钴催化的1,3-烯炔与HBpin选择性硼氢化反应生成1,3-二烯基硼酸酯。使用市售的 Co(acac) 2和 dppf 催化体系，硼氢化反应进展顺利，以中等到高产率提供各种 1,3-二烯基硼酸酯。该方案具有廉价的贱金属催化系统、广泛的底物范围、优异的选择性、易于克级制备和良好的官能团耐受性，并提供了合成有价值的 1,3-二烯基硼酸盐。