[2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethanol | 824952-29-6

• 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(1R*,2S*),3aα,4β,7β,7aα)]-2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethanol
• 英文别名: (1S,2R)-1,2-diphenyl-2-[[(1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-yl]oxy]ethanol
• CAS: 824952-29-6
• 化学式: C₂₆H₃₂O₃
• 分子量: 392.538
• InChiKey: FBZYUBBTGOJVIU-HMNDVOGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethanol 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1R,2S)-2-(2-methylpropoxy)-1,2-diphenylethanol
  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：

  (1S,2R)-1,2-diphenylethane-1,2-diol 、 (2S,2'S-(2α,2'α,3aα,3a'α,4β,4'β,7β,7'β,7aα,7a'α))-2,2'-oxybis[octahydro-7,8,8-trimethyl-4,7-methanobenzofuran] 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 [2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethanol
  参考文献：
  名称：

  Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides

  摘要：

  The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% enantiomeric excess. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.010

文献信息

• Chiral linker. Part 2: Synthesis and evaluation of a novel, reusable solid-supported open chain chiral auxiliary derived from m-hydrobenzoin for the diastereoselective reduction of α-keto esters
  作者：Christian Schuster、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2005.08.030

  日期：2005.10

  Three novel m-hydrobenzoin derived chiral hydrobenzoin mono-alkyl ethers were synthesized and evaluated as open chain chiral auxiliaries in the L-selectride(R)/ZnCl2 mediated stereoselective reduction of their corresponding phenyl glyoxylates, resulting in des of up to 91%. The optimized auxiliary structure was immobilized on commercially available Wang-resin by using the ether substituent as a sublinking unit and applied as a reusable solid-supported chiral auxiliary in the same type of reaction with only little loss of stereofacial selectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides
  作者：Katharina Bica、Peter Gaertner

  DOI：10.1016/j.tetasy.2010.04.010

  日期：2010.4

  The metal-catalyzed stereoselective 1,3-dipolar cycloaddition of azomethine ylides and acrylates using recyclable meso-hydrobenzoin-derived chiral auxiliaries is described. Cleavage of the auxiliary leads to highly substituted pyrrolidines in up to 87% enantiomeric excess. (C) 2010 Elsevier Ltd. All rights reserved.
• 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
  作者：Christian Schuster、Joachim Broeker、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2005.06.033

  日期：2005.8

  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.