(S,S)-3-phenyloxiraneethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-3-phenyloxiraneethanol
• 英文别名: 2-[(2S,3S)-3-phenyloxiran-2-yl]ethanol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: ZCNFBAJNMACHSZ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反-苯乙烯乙酸 在 Chiral ketone Oxone 、 lithium aluminium tetrahydride 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 acetate buffer 、 乙腈 为溶剂， 反应 2.0h， 生成 (S,S)-3-phenyloxiraneethanol
  参考文献：
  名称：

  A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes

  摘要：

  A detailed study shows that the chiral ketone catalyzed asymmetric epoxidations of hydroxyalkenes are highly pH dependent. The lower enantioselectivity obtained at low pH is attributed to the substantial contribution of the direct epoxidation by Oxone. At high pH the epoxidation mediated by chiral ketone out-competes the racemic epoxidation, leading to higher enantioselectivity. The effective substrates include allylic alcohol, homoallylic alcohol, and bishomoallylic alcohol. In most cases, over 90% ee was obtained.

  DOI：

  10.1021/jo972106r

文献信息

• Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation
  作者：Allan U. Barlan、Wei Zhang、Hisashi Yamamoto

  DOI：10.1016/j.tet.2007.03.071

  日期：2007.7

  preliminary results of our new designed C(2)-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.

  在本文中，我们描述了我们新设计的 C(2)-对称双异羟肟酸 (BHA) 配体的开发和初步结果，以及新配体在钒催化烯丙醇和高烯丙醇不对称环氧化中的应用. 从这一成功中，我们证明了 BHA 在钼催化的非官能化烯烃和硫化物的不对称氧化中的多功能性。
• Practical Synthesis of Shi's Diester Fructose Derivative for Catalytic Asymmetric Epoxidation of Alkenes
  作者：N. Nieto、P. Molas、J. Benet-Buchholz、A. Vidal-Ferran

  DOI：10.1021/jo051682h

  日期：2005.11.1

  A practical synthesis of Shi's diester 3 for catalytic asymmetric epoxidations has been developed. The catalyst has been prepared in multigram quantities from d-fructose in four steps with a 66% overall yield. Efficiency, cost, and selectivity aspects of the reagents involved for its preparation have been taken care of during its preparation. The workup procedures have been simplified to the bare minimum

  已经开发了用于催化不对称环氧化的Shi's二酯3的实用合成方法。由d-果糖分四步以克数制备催化剂，总产率为66％。在制备过程中已经考虑到了其制备所涉及的试剂的效率，成本和选择性方面。后处理程序已被简化到最低限度，从而提供了一种非常实用的准备方法。还证明了该催化剂3在α，β-不饱和羰基化合物的环氧化中的众所周知的高效率在未官能化的烯烃中是很高的。
• Catalytic asymmetric epoxidation
  申请人：Yamamoto Hisashi

  公开号：US20050159607A1

  公开（公告）日：2005-07-21

  The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.

  本发明涉及通过催化不对称氧化烯烃合成手性环氧化物。此外，该方法提供了一种不对称氧化硫醚和膦的方法。这种不对称氧化利用了由金属和手性双羟羧酸配体组成的催化剂体系，该体系在存在化学计量氧化试剂的情况下，用于不对称氧化各种底物。
• Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
  作者：Sukalyan Bhadra、Matsujiro Akakura、Hisashi Yamamoto

  DOI：10.1021/jacs.5b11429

  日期：2015.12.23

  A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of gamma-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
• A pH Study on the Chiral Ketone Catalyzed Asymmetric Epoxidation of Hydroxyalkenes
  作者：Zhi-Xian Wang、Yian Shi

  DOI：10.1021/jo972106r

  日期：1998.5.1

  A detailed study shows that the chiral ketone catalyzed asymmetric epoxidations of hydroxyalkenes are highly pH dependent. The lower enantioselectivity obtained at low pH is attributed to the substantial contribution of the direct epoxidation by Oxone. At high pH the epoxidation mediated by chiral ketone out-competes the racemic epoxidation, leading to higher enantioselectivity. The effective substrates include allylic alcohol, homoallylic alcohol, and bishomoallylic alcohol. In most cases, over 90% ee was obtained.