oxophenylacetic acid (1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl ester | 916525-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: oxophenylacetic acid (1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl ester
• 英文别名: [(1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl] 2-oxo-2-phenylacetate
• CAS: 916525-79-6
• 化学式: C₂₈H₂₄F₆O₄
• 分子量: 538.487
• InChiKey: KTHQFWLJLBKSFC-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  oxophenylacetic acid (1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl ester 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到hydroxy(phenyl)acetic acid (1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl ester
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017
• 作为产物：
  描述：

  (1R,2S)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol 在 4-二甲氨基吡啶 、 对甲苯磺酸一水合物 、 sodium hydride 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 oxophenylacetic acid (1R,2S)-2-(2-methylpropoxy)-1,2-bis[2-(trifluoromethyl)phenyl]ethyl ester
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017