[1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan | 916525-65-0

• 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: [1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan
• 英文别名: (1R,2R,4S,6R,7R)-4-[(1R,2S)-1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decane
• CAS: 916525-65-0
• 化学式: C₃₂H₄₄O₃
• 分子量: 476.7
• InChiKey: VKYFUWLKLROZPO-WWRZEJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  [1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan 在 4-二甲氨基吡啶 、 对甲苯磺酸一水合物 、 L-Selectride 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethyl ester
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017
• 作为产物：
  描述：

  2-羟基-1,2-二(2-甲基苯基)乙酮 在 sodium tetrahydroborate 、 对甲苯磺酸一水合物 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 [1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017

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.