[2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-2-[2-(1-benzyl-2-iodo-1-methylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran | 866457-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-2-[2-(1-benzyl-2-iodo-1-methylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran
• 英文别名: (1R,2R,4S,6R,7R)-4-[(1R,2S)-2-(1-iodo-2-methyl-3-phenylpropan-2-yl)oxy-1,2-diphenylethoxy]-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decane
• CAS: 866457-00-3
• 化学式: C₃₆H₄₃IO₃
• 分子量: 650.64
• InChiKey: CNMGOQNXXRYNKI-OVAXKSHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-2-[2-(1-benzyl-2-iodo-1-methylethoxy)-1,2-diphenyl-ethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 16.0h， 以90%的产率得到[2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(1,1-dimethyl-2-phenylethoxy)-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
• 作为产物：
  描述：

  [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-benzylpropionic acid 1,1-dimethylethyl ester 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 三苯基膦 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-2-[2-(1-benzyl-2-iodo-1-methylethoxy)-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