[2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(2-methoxy-1,1-dimethylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran | 866456-96-4

• 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: [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(2-methoxy-1,1-dimethylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran
• CAS: 866456-96-4
• 化学式: C₃₁H₄₂O₄
• 分子量: 478.672
• InChiKey: YEHNWKZPZKMFJD-KPJHTNHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(2-methoxy-1,1-dimethylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 oxophenylacetic acid [1R,2S]-2-(2-methoxy-1,1-dimethylethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters

  摘要：

  Three m-hydroberizoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new, reaction pathway and tested as chiral auxiliaries in the L-selectride (R) mediated stereoselective reduction of their corresponding phellyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.033
• 作为产物：
  描述：

  methanesulfonic acid [2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethoxy]-2-methylpropyl ester 在 sodium hydride 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(2-methoxy-1,1-dimethylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran
  参考文献：
  名称：

  Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters

  摘要：

  Three m-hydroberizoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new, reaction pathway and tested as chiral auxiliaries in the L-selectride (R) mediated stereoselective reduction of their corresponding phellyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.033