[2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethoxy]ethanol | 870298-15-0

• 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-[2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethoxy]ethanol
• CAS: 870298-15-0
• 化学式: C₂₈H₃₆O₄
• 分子量: 436.591
• InChiKey: OLAWYLXUPCBTMF-UESYHMFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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]ethanol 在 4-二甲氨基吡啶 、 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 、 甲苯 为溶剂， 反应 48.0h， 生成 3-oxo-3-phenylpropionic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2005.08.030
• 作为产物：
  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 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 1.0h， 生成 [2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethoxy]ethanol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2005.08.030

文献信息

• 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.