2,3-dihydroxy-1-phenylpropan-1-one | 5792-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dihydroxy-1-phenylpropan-1-one
• 英文别名: 2,3-dihydropropiophenone；α,β-dihydroxypropiophenone；2,3-dihydroxy-1-phenyl-propan-1-one；2,3-Dihydroxy-1-phenyl-propan-1-on；1-Phenyl-2,3-dihydroxy-1-propanone；1-Phenyl-2,3-dihydroxy-1-propanon；Monobenzoylglykol
• CAS: 5792-35-8
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: JOMKEHIPJGGZKN-UHFFFAOYSA-N

物化性质

• 熔点：
  81.5 °C(Solv: ethyl ether (60-29-7); benzene (71-43-2))
• 沸点：
  150-151 °C(Press: 10 Torr)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 2,3-dihydroxy-1-phenylpropan-1-one 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (1S,2S)-1-phenylpropane-1,2,3-triol 、 [S(R*,R*)]-1-苯基甘油
  参考文献：
  名称：

  Cahnmann, Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 226,230

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二羟基-1-苯基丙烷-2-酮 以 水 为溶剂， 生成 2,3-dihydroxy-1-phenylpropan-1-one
  参考文献：
  名称：

  Stereoselectivity of an ω-transaminase-mediated amination of 1,3-dihydroxy-1-phenylpropane-2-one

  摘要：

  The stereoselectivity of a recently isolated omega-transaminase from Chromobacterium violaceum in the amination of 1,3-dihydroxy-1-phenylpropan-2-one has been determined. The enzyme is not enantioselective towards a racemic mixture of 1,3-dihydroxy-1-phenylpropan-2-one but is highly stereoselective forming (2S)-2-amino-1-phenyl-1,3-propanediols in >99% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.012

文献信息

• A Simple and Highly Selective Biomimetic Oxidation of Alcohols and Epoxides withN-Bromosuccinimide in the Presence ofβ-Cyclodextrin in Water
  作者：N. Srilakshmi Krishnaveni、K. Surendra、K. Rama Rao

  DOI：10.1002/adsc.200303164

  日期：2004.2

  A simple, mild and highly efficient biomimetic oxidation of various alcohols and epoxides with N-bromosuccinimide (NBS) catalyzed by β-cyclodextrin in water has been developed. A series of alcohols and epoxides were oxidized selectively at room temperature in excellent yields. This method is a direct one-pot synthesis under mild conditions using water as solvent and has many advantages over the existing

  已经开发了由β-环糊精在水中催化的N-溴丁二酰亚胺（NBS）简单，温和，高效的仿生氧化各种醇和环氧化物的方法。一系列醇和环氧化物在室温下选择性氧化，收率很高。该方法是在温和条件下使用水作为溶剂的直接一锅法合成，与现有方法相比具有许多优点。
• Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents
  作者：George Ward、Charles L. Liotta、Ramanarayanan Krishnamurthy、Stefan France

  DOI：10.1021/acs.joc.8b01867

  日期：2018.12.7

  derivative of dihydroxyfumaric acid (DHF) has been used exclusively as an electrophile in organic synthesis. However, the synthetic utility of DHF’s nucleophilic reactivity, contained in the ene–diol moiety, has been underexplored. Inspired by recently observed pH-dependent chemodivergent nucleophilic aldol reactions of dihydroxyfumarate (DHF2–) with glyoxylate and formaldehyde, we report herein the control

  二羟基富马酸（DHF）的二酯衍生物已专门用作有机合成中的亲电子试剂。然而，烯-二醇部分中所含的DHF亲核反应性的合成效用尚未得到开发。受到最近观察到的二羟基富马酸酯的pH依赖性化学发散亲核醛醇缩合反应（DHF 2–）与乙醛酸酯和甲醛，我们在此报告二羟基富马酸酯与芳族和杂芳族醛之间碱控制的化学发散反应的控制和合成应用。在主要的水性介质中，以氢氧化物为碱，先进行羟醛加成，然后进行脱草酸作用，得到各种3-芳基-2，3-二羟基丙酸。以三乙胺为THF中的碱，1-芳基-2,3-二羟基丙烷是反应的产物。为了了解DHF，其二羧酸盐和其二甲基酯之间反应性的差异，我们进行了计算和实验研究，它们为为什么富马酸二羟基酯（DHF 2–）是亲核试剂而相应的二酯以亲电子试剂反应的原因提供了理论依据。。
• Tandem Benzylic Oxidation/Dihydroxylation of<i>α</i>-Vinyl- and<i>α</i>-Alkenylbenzyl Alcohols
  作者：Rodney A. Fernandes、Pullaiah Kattanguru

  DOI：10.1002/hlca.201400143

  日期：2015.1

  A de novo tandem benzylic oxidative dihydroxylation of α‐vinyl‐ and α‐alkenylbenzyl alcohols has been developed to give α,β‐dihydroxypropiophenones (=2,3‐dihydroxy‐1‐phenylpropan‐1‐ones) and α,β‐dihydroxyalkyl phenones. This method was shown to be substrate‐selective and specific for the oxidation of benzylic alcohols.

  甲从头的串联苄氧化二羟基α -vinyl-和α -alkenylbenzyl醇已被开发，得到α，β -dihydroxypropiophenones（= 2,3-二羟基-1-苯基丙-1-酮）和α，β -dihydroxyalkyl苯酮。该方法显示出对底物有选择性，并且对苯甲醇的氧化具有特异性。
• Decarboxylative Cascade Reactions of Dihydroxyfumaric Acid: A Preparative Approach to the Glyoxylate Scenario
  作者：Celin Richter、Falko Berndt、Tom Kunde、Rainer Mahrwald

  DOI：10.1021/acs.orglett.6b01287

  日期：2016.6.17

  An operationally simple protocol is reported to generate an α-hydroxyacyl anion by the decarboxylation of dihydroxyfumaric acid. To date, the “missing” utilization of the hydroxyacyl anion in highly chemo- and stereoselective cascade reactions enables short and direct construction of carbohydrates.

  据报道，一种操作简单的方案通过二羟基富马酸的脱羧生成α-羟酰基阴离子。迄今为止，在高度化学和立体选择性的级联反应中“缺少”利用羟酰基阴离子可实现碳水化合物的短而直接的构建。
• The Enhancement of Formose Formation with 2-Hydroxyacetophenone. A Mechanism Involving Aldol and Retro-aldol Reactions
  作者：Tomoya Sakai、Masahiko Ishizaki、Masafumi Goto

  DOI：10.1246/bcsj.55.2409

  日期：1982.8

  were formed, accompanied by formose sugars. The initial molar amount of HAP corresponded to the sum of the compounds substituted with the phenyl group including benzaldehyde and benzoic acid. The retro-aldol reaction of the HAP derivatives is likely to be involved in the overall reaction to yield glycolaldehyde or trioses, which are good accelerators for formose formation.

  将甲醛快速羟醛加成到 2-羟基苯乙酮 (HAP) 中，这是一种有效的甲醛形成促进剂，在 35°C 下，在 40% 的甲醛甲醇混合物中，产生 HAP 与一分子和两分子甲醛的加成产物， HAP 和 Ca(OH)2。在整个反应过程中，没有检测到另外的加成产物有超过两个分子的甲醛附着在 HAP 上。相反，形成了苯甲醛和苯甲酸，伴随着甲糖。HAP 的初始摩尔量对应于被苯基取代的化合物的总和，包括苯甲醛和苯甲酸。HAP 衍生物的逆羟醛反应很可能参与生成乙醇醛或丙糖的整个反应，它们是形成甲糖的良好促进剂。