(1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethanol | 870298-20-7

• 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: (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethanol
• CAS: 870298-20-7
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: UGZBQFFNYYJEJJ-SJORKVTESA-N

物化性质

• 沸点：
  381.5±37.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethanol 在 4-二甲氨基吡啶 、 magnesium 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (R)-2-hydroxy-2,6-dimethylhept-6-enoic acid, (1R,2S)-2-(2-methoxyethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin

  摘要：

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.016
• 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 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 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-methoxyethoxy)-1,2-diphenylethanol
  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

• Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses
  作者：Joachim Broeker、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2009.02.004

  日期：2009.2

  The applicability of five aryl substituted m-hydrobenzoin ethers already tested in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates as open chain chiral auxiliaries was further investigated via the alpha-alkylation of propionates, the addition of n-BuZnCl to phenylglyoxylates and the Diels-Alder reaction of acrylates with cyclopentadiene as model reactions. As up to 90% cle could be achieved in the solution phase, two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliaries in the same type of reactions. (C) 2009 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.
• Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin
  作者：Christian Schuster、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2006.08.016

  日期：2006.9

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.