3-Methyl-5-phenylpent-4-yn-1-ol | 204760-54-3

• 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: 3-Methyl-5-phenylpent-4-yn-1-ol
• CAS: 204760-54-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: YTENODTUTYBAIH-UHFFFAOYSA-N

物化性质

• 沸点：
  304.8±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methyl-5-phenylpent-4-yn-1-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以94 %的产率得到3-甲基-5-苯基戊醇
  参考文献：
  名称：

  不同有机金属试剂激活的 1,3-双（硼）酯的可控区域发散烷基化

  摘要：

  开发了一种使用不同的有机金属试剂对 1,3-双（硼）酯进行可控区域发散炔基化的有效方法。机理研究表明，独特的螯合模式对于确定选择性至关重要。这种方法克服了与通过自由基机制进行偶联反应相关的缺点，该机制通常产生通过稳定自由基物质反应的经典产物。

  DOI：

  10.1002/anie.202312605
• 作为产物：
  描述：

  4-((tert-butyldimethylsilyl)oxy)-2-methylbutan-1-ol 在 正丁基锂 、 草酰氯 、 Pd catalyst 、 三氟化硼乙醚 、 二甲基亚砜 、 三苯基膦 作用下， 生成 3-Methyl-5-phenylpent-4-yn-1-ol
  参考文献：
  名称：

  Stereoselective Preparation of Vitamin D Precursors Using the Intramolecular Coupling of Alkynes and Cyclopropylcarbene−Chromium Complexes:  A Formal Total Synthesis of (±)-Vitamin D₃

  摘要：

  The intramolecular coupling of alkynes and cyclopropylcarbene-chromium complexes has been examined. Complexes that feature a stereogenic center at the propargylic position of the alkyne-carbene tether are the focus of this paper. The reaction produces a cyclopentadienone intermediate fused to an oxygen heterocycle, which is reduced to the corresponding cyclopentenone under the reaction conditions (100 degrees C in aqueous toluene). The preexisting stereogenic center has a powerful influence on the reduction of the cyclopentadienone ring, and predominantly a single diastereomer is produced in the reaction. Reductive cleavage of the heterocyclic ring with retention of stereochemistry affords compounds featuring a stereocenter on the five-membered ring and on a side chain. Use of the above reaction processes for the synthesis of the vitamin D precursor de-ABC-cholestan-14-one is also discussed.

  DOI：

  10.1021/jo972186z

文献信息

• Stereoselective Preparation of Vitamin D Precursors Using the Intramolecular Coupling of Alkynes and Cyclopropylcarbene−Chromium Complexes:  A Formal Total Synthesis of (±)-Vitamin D₃
  作者：Jingbo Yan、James W. Herndon

  DOI：10.1021/jo972186z

  日期：1998.4.1

  The intramolecular coupling of alkynes and cyclopropylcarbene-chromium complexes has been examined. Complexes that feature a stereogenic center at the propargylic position of the alkyne-carbene tether are the focus of this paper. The reaction produces a cyclopentadienone intermediate fused to an oxygen heterocycle, which is reduced to the corresponding cyclopentenone under the reaction conditions (100 degrees C in aqueous toluene). The preexisting stereogenic center has a powerful influence on the reduction of the cyclopentadienone ring, and predominantly a single diastereomer is produced in the reaction. Reductive cleavage of the heterocyclic ring with retention of stereochemistry affords compounds featuring a stereocenter on the five-membered ring and on a side chain. Use of the above reaction processes for the synthesis of the vitamin D precursor de-ABC-cholestan-14-one is also discussed.
• Controllable Regiodivergent Alkynylation of 1,3‐Bis(Boronic) Esters Activated by Distinct Organometallic Reagents
  作者：Ang Chen、Yang Qiao、De‐Wei Gao

  DOI：10.1002/anie.202312605

  日期：2023.11.27

  An efficient method for controllable regiodivergent alkynylation of 1,3-bis(boronic) esters using distinct organometallic reagents has been developed. Mechanistic studies revealed that unique chelation patterns are essential in determining selectivity. This approach overcomes the drawbacks associated with coupling reactions through radical mechanisms, which commonly yield the classical products reacting

  开发了一种使用不同的有机金属试剂对 1,3-双（硼）酯进行可控区域发散炔基化的有效方法。机理研究表明，独特的螯合模式对于确定选择性至关重要。这种方法克服了与通过自由基机制进行偶联反应相关的缺点，该机制通常产生通过稳定自由基物质反应的经典产物。