3-bromo-6-phenyl-3-hexen-1-yne | 294634-84-7

• 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: 3-bromo-6-phenyl-3-hexen-1-yne
• 英文别名: [(Z)-4-bromohex-3-en-5-ynyl]benzene
• CAS: 294634-84-7
• 化学式: C₁₂H₁₁Br
• 分子量: 235.123
• InChiKey: OKHMGHADKMUSAA-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-bromo-6-phenyl-3-hexen-1-yne 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以97%的产率得到(Z)-4-bromo-7-phenyl-4-hepten-2-yne
  参考文献：
  名称：

  Studies on stereoselective Sonogashira coupling of 1,1-dibromo-1-alkene

  摘要：

  The stercoselective Sonogashira coupling of 1,1-dibromo-l-alkene was described. The use of PdCl2(dppf) as a catalyst with trialkylsilylacetylene in benzene selectively gave the (Z)-bromoenyne (2a) along with small amounts of the enediyne (3a). Based on the experimental results, a mechanism of the selectivity was proposed. The bromoenyne was coupled with some electrophiles to give the substituted (Z)-bromoenynes after deprotection. of the terminal silyl group. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01262-7
• 作为产物：
  描述：

  4-phenyl-1,1-dibromo-1-butene 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 3-bromo-6-phenyl-3-hexen-1-yne
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of Butatrienes

  摘要：

  以2-溴-1-丁烯-3-炔衍生物和亲核试剂为起始材料，成功实现了铂催化的功能化丁四烯合成。反应在非常温和的条件下进行，产物的收率为中等到良好。溴丁烯炔底物的反应性高度依赖于1位的取代基。亲核剂的亲核性和碱性之间的微妙平衡对于反应的成功也至关重要。

  DOI：

  10.1246/cl.2000.776

文献信息

• Palladium-Catalyzed Synthesis of Butatrienes
  作者：Masamichi Ogasawara、Hisashi Ikeda、Kazunori Ohtsuki、Tamio Hayashi

  DOI：10.1246/cl.2000.776

  日期：2000.7

  Palladium-catalyzed synthesis of functionalized butatrienes was achieved starting from 2-bromo-1-buten-3-yne derivatives and nucleophiles. The reaction proceeded under very mild conditions giving the products in moderate to good yields. The reactivity of the bromobutenyne substrates was highly dependent on substituents at 1-position. A subtle balance of nucleophilicity and basicity in the nucleophiles was also important for the success of the reactions.

  以2-溴-1-丁烯-3-炔衍生物和亲核试剂为起始材料，成功实现了铂催化的功能化丁四烯合成。反应在非常温和的条件下进行，产物的收率为中等到良好。溴丁烯炔底物的反应性高度依赖于1位的取代基。亲核剂的亲核性和碱性之间的微妙平衡对于反应的成功也至关重要。
• Studies on stereoselective Sonogashira coupling of 1,1-dibromo-1-alkene
  作者：Jun'ichi Uenishi、Katsuaki Matsui、Hirohisa Ohmiya

  DOI：10.1016/s0022-328x(02)01262-7

  日期：2002.7

  The stercoselective Sonogashira coupling of 1,1-dibromo-l-alkene was described. The use of PdCl2(dppf) as a catalyst with trialkylsilylacetylene in benzene selectively gave the (Z)-bromoenyne (2a) along with small amounts of the enediyne (3a). Based on the experimental results, a mechanism of the selectivity was proposed. The bromoenyne was coupled with some electrophiles to give the substituted (Z)-bromoenynes after deprotection. of the terminal silyl group. (C) 2002 Elsevier Science B.V. All rights reserved.