(3R)-2,2-dimethyl-3-phenylbutyric acid | 16460-93-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (3R)-2,2-dimethyl-3-phenylbutyric acid
• 英文别名: (-)-(S)-2,2-Dimethyl-3-phenyl-buttersaeure；(3R)-2,2-dimethyl-3-phenylbutanoic acid
• CAS: 16460-93-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: USKSYHPGALFBIV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (3R)-2,2-dimethyl-3-phenylbutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(3R)-2,2-dimethyl-3-phenylbutyric acid
  参考文献：
  名称：

  An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

  摘要：

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.040

文献信息

• An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides
  作者：Shimpei Sugiyama、Nobuhito Nakaya、Tsuyoshi Satoh

  DOI：10.1016/j.tetasy.2008.01.040

  日期：2008.3

  Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides with two different substituents at the 2-position, which were synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps, with the lithium enolate of carboxylic acid tert-butyl esters gave the adducts with substituents at the alpha- and beta-position with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center in high yields. The adducts were converted to optically active esters and gamma-lactones having stereogenic centers at the alpha- and beta-position in good to high yields. This procedure offers a new method for a synthesis of optically active carboxylic acid derivatives with stereogenic centers at the alpha- and beta-position. (C) 2008 Elsevier Ltd. All rights reserved.