(1R,2S,5R)-8-phenylmenthyl (R)-2-formyl-2-(2-phenylprop-1-enyl)-2-phenylacetate | 1011515-84-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R,2S,5R)-8-phenylmenthyl (R)-2-formyl-2-(2-phenylprop-1-enyl)-2-phenylacetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (E,2R)-2-formyl-2,4-diphenylpent-3-enoate
• CAS: 1011515-84-6
• 化学式: C₃₄H₃₈O₃
• 分子量: 494.674
• InChiKey: YKERCZXZLNCMQC-HXBTUCHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-苯基丁-2-烯醛 、 (-)-(1R,3R,4S)-8-phenylmenthyl 2-diazo-2-phenylacetate 在 三氟甲磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (1R,2S,5R)-8-phenylmenthyl (R)-2-formyl-2-(2-phenylprop-1-enyl)-2-phenylacetate 、 (1R,2S,5R)-8-phenylmenthyl (S)-2-formyl-2-(2-phenylprop-1-enyl)-2-phenylacetate
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Insertion of Aryldiazoacetates to sp² Carbon−CHO Bond:  Facile Construction of Chiral All-Carbon Quaternary Center

  摘要：

  Aryldiazoacetates could be formally inserted into the carbon-carbon bond of the Bronsted acid-activated aromatic and alpha,beta-unsaturated aldehydes. Use of phenylmenthyl esters allowed the asymmetric induction at the inserted all-carbon quaternary carbon center with the excellent stereoselectivities.

  DOI：

  10.1021/ja710532j

文献信息

• Brønsted Acid-Catalyzed Insertion of Aryldiazoacetates to sp² Carbon−CHO Bond:  Facile Construction of Chiral All-Carbon Quaternary Center
  作者：Takuya Hashimoto、Yuki Naganawa、Keiji Maruoka

  DOI：10.1021/ja710532j

  日期：2008.2.1

  Aryldiazoacetates could be formally inserted into the carbon-carbon bond of the Bronsted acid-activated aromatic and alpha,beta-unsaturated aldehydes. Use of phenylmenthyl esters allowed the asymmetric induction at the inserted all-carbon quaternary carbon center with the excellent stereoselectivities.