[(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate | 221099-73-6

• 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: [(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate
• CAS: 221099-73-6
• 化学式: C₃₀H₃₀O₄
• 分子量: 454.566
• InChiKey: MFMFSZGJQFRHAV-ITLAICGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate 在 sodium hydroxide 、 LiAlH(OCEt₃)3 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 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：

  ketopinic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate
  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

文献信息

• Novel Camphor-Derived Chiral Auxiliaries:  Significant Solvent and Additive Effects on Asymmetric Reduction of Chiral α-Keto Esters
  作者：Ying-Yuan Chu、Chia-Sheng Yu、Chiou-Juy Chen、Kung-Shuo Yang、Jung-Chaing Lain、Chun-Hui Lin、Kwunmin Chen

  DOI：10.1021/jo9902188

  日期：1999.9.1

  Stereoselective reduction of various alpha-keto esters 5a-d derived from exo-10,10-diphenyl-2,10-camphanediol 4a and exo-10,10-diphenyl-10-methoxy-2-camphanol 4b is described. High to excellent diastereomeric excess (99% de) with good chemical yields is obtained. The sense of stereoselectivity as a function of C10 modification is remarkable. Further, in the case of 5d, both diastereomers of a-hydroxyl esters can be obtained with excellent optical purity by the appropriate choice of reaction conditions. The influence of the solvents and additives on the reaction course has been investigated.
• Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction
  作者：Chiou-Juy Chen、Ying-Yuan Chu、Yen-Ying Liao、Zong-Hugh Tsai、Chiung-Chiou Wang、Kwunmin Chen

  DOI：10.1016/s0040-4039(98)02548-9

  日期：1999.2

  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.