5-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-4-yn-1-ol | 175410-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 5-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-4-yn-1-ol
• CAS: 175410-80-7
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: JXMCYMPJTIHEAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-4-yn-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 bipyrindine derivative copper 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone

  摘要：

  Chiral bipyrindine and biquinoline which have been reported to be efficient Ligands for the construction of chiral copper catalysts, were synthesized enantioselectively by rising Mn-salen catalyzed asymmetric epoxidation as a key step. Enantioselective synthesis of trans-whisky lactone was then achieved by way of enantiospecific ring expansion reaction of oxetane with a chiral copper catalyst bearing the bipyrindine Ligand as a chiral source.

  DOI：

  10.1016/s0040-4020(96)00058-0
• 作为产物：
  描述：

  ethyl dl-5-phenyl-3-(2-tetrahydropyranyloxy)-4-pentynoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 5-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-4-yn-1-ol
  参考文献：
  名称：

  Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone

  摘要：

  Chiral bipyrindine and biquinoline which have been reported to be efficient Ligands for the construction of chiral copper catalysts, were synthesized enantioselectively by rising Mn-salen catalyzed asymmetric epoxidation as a key step. Enantioselective synthesis of trans-whisky lactone was then achieved by way of enantiospecific ring expansion reaction of oxetane with a chiral copper catalyst bearing the bipyrindine Ligand as a chiral source.

  DOI：

  10.1016/s0040-4020(96)00058-0

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.
• Synthesis of Alkylidenecyclopentenones and Dialkylidenecyclopentenones via the Coupling of Propargylic Alcohol and 2-Alkyne-1,4-diol Derivatives with Cyclopropylcarbene–Chromium Complexes
  作者：James W Herndon、Jin Zhu、Diego Sampedro

  DOI：10.1016/s0040-4020(00)00212-x

  日期：2000.7

  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.