7-phenyl-6-penten-4-yne-1,3-diol 3-dihydropyranyl ether | 235094-53-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-phenyl-6-penten-4-yne-1,3-diol 3-dihydropyranyl ether
• CAS: 235094-53-8
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: QTNOQFFNYFYZMD-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-phenyl-6-penten-4-yne-1,3-diol 3-dihydropyranyl ether 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酰氯 、 水 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 以24%的产率得到(5Z)-5-(2-phenylethylidene)-2,3-dihydrocyclopenta[b]pyran-6-one
  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
• 作为产物：
  描述：

  (E)-5-phenylpent-4-en-2-ynal 在 锂硼氢 、 锌 作用下， 生成 7-phenyl-6-penten-4-yne-1,3-diol 3-dihydropyranyl ether
  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.