(R)-Hydroxy-phenyl-acetic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 221099-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-Hydroxy-phenyl-acetic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-hydroxy-2-phenylacetate
• CAS: 221099-74-7
• 化学式: C₃₀H₃₂O₄
• 分子量: 456.582
• InChiKey: VOKVTYQHAVWOTG-GSTLAZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-Hydroxy-phenyl-acetic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到exo-10,10-diphenyl-2,10-camphanediol
  参考文献：
  名称：

  Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

  摘要：

  Stereoselective reduction of alpha-keto ester derived from exo-10, 10-diphenyl-2, 10-camphanediol with various hydrides proceeded with high diastereoselectivities (greater than or equal to 96% de) to afford the corresponding alpha-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02548-9
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 在 LiAlH(OCEt₃)3 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (R)-Hydroxy-phenyl-acetic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

  摘要：

  Stereoselective reduction of alpha-keto ester derived from exo-10, 10-diphenyl-2, 10-camphanediol with various hydrides proceeded with high diastereoselectivities (greater than or equal to 96% de) to afford the corresponding alpha-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02548-9