(1S,2R)-2-Ethoxy-1,2-diphenyl-ethanol | 877384-24-2

• 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: (1S,2R)-2-Ethoxy-1,2-diphenyl-ethanol
• 英文别名: (1S,2R)-2-ethoxy-1,2-diphenylethanol
• CAS: 877384-24-2
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: GATJXTZLXKIOIJ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  安息香乙醚 在 Pt/Al₂O₃ 、 (8alpha,9R)-10,11-二氢脱氧辛可宁-9-醇 氢气 作用下， 以 甲苯 为溶剂， 25.0 ℃ 、6.0 MPa 条件下， 反应 0.22h， 生成 (1R,2S)-2-ethoxy-1,2-diphenylethan-1-ol 、 (1S,2R)-2-Ethoxy-1,2-diphenyl-ethanol
  参考文献：
  名称：

  Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base

  摘要：

  The first successful example of the asymmetric hydrogenation of substituted a-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of < 50%. Addition of KOH gave a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of > 80% were obtained at > 95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.

  DOI：

  10.1002/1615-4169(200207)344:5<511::aid-adsc511>3.0.co;2-d

文献信息

• Medium Effects on Stereochemistry of Acid-Catalyzed Ethanolysis of<i>trans</i>-2,3-Diphenyloxirane
  作者：Masashi Inoue、Yoshio Taguchi、Toshio Sugita、Katsuhiko Ichikawa

  DOI：10.1246/bcsj.51.2098

  日期：1978.7

  The acid catalyzed ethanolysis of trans-2,3-diphenyloxirane was examined in a wide variety of binary ethanolic solvent systems. The reaction proceeded with 26% retention and 74% inversion of configuration in pure ethanol at 50 °C. The dilution of ethanol by hexane or benzene produced almost no change in stereochemistry of the ethanolysis. The addition of acetonitrile, nitromethane, or sulfolane to the ethanolic solution resulted in increased degrees of retention. In binary ethanolic mixtures containing DMSO, DMF, or HMPA, increased ratios of inverted product were obtained. The steric course of the ethanolysis could be controlled from 85% retention–15% inversion (CH3NO2:ethanol=20:2 by volume) to 10% retention–90% inversion (HMPA: ethanol=10:12) by the choice of co-solvent. The results are discussed in terms of the solvation-shell concept.

  在多种二元乙醇溶剂体系中对反式-2,3-二苯基环氧乙烷的酸催化乙醇分解进行了研究。在 50 °C 的纯乙醇中，反应的保留率为 26%，构型反转率为 74%。用正己烷或苯稀释乙醇几乎不会改变乙醇分解的立体化学结构。在乙醇溶液中加入乙腈、硝基甲烷或磺烷会增加保留度。在含有 DMSO、DMF 或 HMPA 的二元乙醇混合物中，得到的反相产物比例增加。通过选择助溶剂，乙醇分解的立体过程可从 85% 的保留-15% 的反转（CH3NO2:乙醇=20:2（体积比））控制到 10% 的保留-90% 的反转（HMPA:乙醇=10:12）。本研究从溶壳概念的角度对结果进行了讨论。
• US7173141B2
  申请人：——

  公开号：US7173141B2

  公开（公告）日：2007-02-06
• Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base
  作者：Martin Studer、Hans-Ulrich Blaser、Stephan Burkhardt

  DOI：10.1002/1615-4169(200207)344:5<511::aid-adsc511>3.0.co;2-d

  日期：2002.7

  The first successful example of the asymmetric hydrogenation of substituted a-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of < 50%. Addition of KOH gave a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of > 80% were obtained at > 95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.