1-acetoxy-5-phenylpent-4-en-2-yne | 103240-57-9

• 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: 1-acetoxy-5-phenylpent-4-en-2-yne
• 英文别名: 5-phenyl-4-penten-2-yn-1-yl acetate；5-phenyl-4-penten-2-ynyl acetate；[(E)-5-phenylpent-4-en-2-ynyl] acetate
• CAS: 103240-57-9
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: QQDWXTJUOSBFNA-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Zinc, chlorophenyl- 、 1-acetoxy-5-phenylpent-4-en-2-yne 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以57%的产率得到1,3-二苯基戊-1,3,4-三烯
  参考文献：
  名称：

  Palladium-catalyzed propargylic vs. allylic alkylation

  摘要：

  DOI：

  10.1021/jo00371a018
• 作为产物：
  描述：

  [(Z)-2-溴乙烯基]苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 生成 1-acetoxy-5-phenylpent-4-en-2-yne
  参考文献：
  名称：

  Synthesis of Alkylidenecyclopentenones and Dialkylidenecyclopentenones via the Coupling of Propargylic Alcohol and 2-Alkyne-1,4-diol Derivatives with Cyclopropylcarbene–Chromium Complexes

  摘要：

  The coupling of propargylic alcohols and their derivatives with cyclopropylcarbene-chromium complexes has been investigated. The coupling reaction leads to alkylidenecyclopentenones or alkoxyalkyl-cyclopentenones, depending on the leaving group ability of the propargyl substituent. A mechanism involving formation of a cyclopentadienone, followed by reduction and beta-elimination is proposed. Coupling of cyclopropylcarbene complexes with 2-alkyne-1,4-diol derivatives leads to dialkylidenecyclopentenone derivatives via a double elimination process. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00212-x

文献信息

• Synthesis of Alkylidenecyclopentenones via the Coupling of Propargyl Alcohol Derivatives with Cyclopropylcarbene−Chromium Complexes
  作者：James W. Herndon、Jin Zhu

  DOI：10.1021/ol990002s

  日期：1999.7.1

  The coupling of propargylic alcohols and their derivatives with cyclopropylcarbene-chromium complexes has been investigated. The coupling reaction leads to alkylidenecyclopentenones or alkoxyalkylcyclopentenones, depending on the leaving group ability of the propargyl substituent. A mechanism involving formation of a cyclpentadienone, followed by reduction and beta-elimination, was proposed.
• KEINAN E.; BOSCH E., J. ORG. CHEM., 51,(1986) N 21, 4006-4016
  作者：KEINAN E.、 BOSCH E.

  DOI：——

  日期：——