methyl (3R)-5-naphthalen-2-yl-5-oxo-3-phenylpentanoate | 1616107-92-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl (3R)-5-naphthalen-2-yl-5-oxo-3-phenylpentanoate
• CAS: 1616107-92-6
• 化学式: C₂₂H₂₀O₃
• 分子量: 332.399
• InChiKey: DQBHFBHHVGCWAU-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  在 碘甲烷 、 盐酸 、 水 作用下， 以 正戊烷 为溶剂， 反应 48.5h， 以93%的产率得到methyl (3R)-5-naphthalen-2-yl-5-oxo-3-phenylpentanoate
  参考文献：
  名称：

  The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition

  摘要：

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.049

文献信息

• The preparation of novel chiral auxiliaries SAMIQ/RAMIQ and their application in the asymmetric Michael addition
  作者：Xuan Pan、Zhanzhu Liu

  DOI：10.1016/j.tet.2014.05.049

  日期：2014.8

  A pair of novel chiral auxiliaries SAMIQ/RAMIQ was synthesized from L- or D-phenylalanine methyl ester hydrochloride over six steps in 45.8% and 44.4% yield, respectively. The SAMIQ-/RAMIQ-hydrazone methodology was applied for the asymmetric Michael addition of ketones to alpha,beta-unsaturated carboxylic acid methyl esters, which afforded 3-substituted-5-oxo-alkanoates in moderate to good yield (65-82%) with excellent enantioselectivity (ee=95.3%similar to>99.5%). (C) 2014 Elsevier Ltd. All rights reserved.