[(1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate | 249739-62-6

• 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-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate
• CAS: 249739-62-6
• 化学式: C₃₁H₃₂O₄
• 分子量: 468.593
• InChiKey: UFUJRRMBDALONG-VOKYQHOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate 在 L-Selectride 作用下， 以 甲苯 为溶剂， 以98%的产率得到[(1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-hydroxy-2-phenylacetate
  参考文献：
  名称：

  Novel Camphor-Derived Chiral Auxiliaries:  Significant Solvent and Additive Effects on Asymmetric Reduction of Chiral α-Keto Esters

  摘要：

  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.

  DOI：

  10.1021/jo9902188
• 作为产物：
  描述：

  ketopinic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [(1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate
  参考文献：
  名称：

  Novel Camphor-Derived Chiral Auxiliaries:  Significant Solvent and Additive Effects on Asymmetric Reduction of Chiral α-Keto Esters

  摘要：

  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.

  DOI：

  10.1021/jo9902188

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.