Hydrobenzoin-monoacetat

• 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: Hydrobenzoin-monoacetat
• 英文别名: α'-acetoxy-bibenzyl-α-ol；1,2-Diphenyl-2-acetoxyethanol；(2-hydroxy-1,2-diphenylethyl) acetate
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: MIEQNLYINCRPLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Hydrobenzoin-monoacetat 、 乙酸酐 生成 1,2-二苯基乙烯二乙酸酯
  参考文献：
  名称：

  Forst; Zincke, Justus Liebigs Annalen der Chemie, 1876, vol. 182, p. 282

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-1,2-二苯乙烯 、 溶剂黄146 在 [Pd(dppp)(H₂O)2]⁽²⁺⁾*2(OTf)^(1-) 碘苯二乙酸 、 水 作用下， 反应 2.0h， 生成 Hydrobenzoin-monoacetat
  参考文献：
  名称：

  Palladium-Catalyzed Olefin Dioxygenation

  摘要：

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.

  DOI：

  10.1021/ja711029u

文献信息

• Oxidation by cobalt(III) acetate. Part 6. A novel synthesis of the glycol monoacetates from aromatic olefins in wet acetic acid
  作者：Masao Hirano、Takashi Morimoto

  DOI：10.1039/p29840001033

  日期：——

  Oxidation of various aryl-conjugated olefins with cobalt(III) acetate in wet acetic acid under nitrogen affords the glycol monoacetates in moderate to good yields. None of the phenyl rearrangement product is formed in the present reactions. These results are best interpreted by assuming the formation of a Co-co-ordinated intermediate.

  在湿乙酸中，在氮气下用乙酸钴（III）在乙酸中氧化各种芳基共轭烯烃，可得到中等收率的乙二醇单乙酸酯。在本反应中没有形成苯基重排产物。通过假设形成一个协同中间体，可以最好地解释这些结果。
• Mechanisms for Manganese(III) Oxidations with Alkenes
  作者：William E. Fristad、John R. Peterson、Andreas B. Ernst、Gordon B. Urbi

  DOI：10.1016/s0040-4020(01)87310-5

  日期：1986.1

  metal complexed organic radicals, and the importance of an oxo-centered manganese(III) triangle are discussed as they relate to the lactone annulation reaction. Single electron transfer oxidation of alkenes is described as a route toward 1,2-diacetates of alkenes within the 8.1-7.5 eV I.P. range. Three less common modes of Mn(III) reaction are discussed and compared with the two primary processes of

  在乙酸锰（III）与羧酸和烯烃的反应中，已经鉴定出三个不同的过程，它们涉及烯烃和两个独立于烯烃的过程。通过产品研究，重排，稀释实验和文献动力学数据的组合，可以提出一个统一的机制图来描述这些过程。具体地，讨论了羧酸组分的α-H酸的作用，缺电子的自由基加成，金属络合的有机自由基以及以氧代为中心的锰（III）三角形的重要性，因为它们与内酯环化反应有关。烯烃的单电子转移氧化被描述为通往8.1-7.5 eV IP范围内的烯烃1,2-二乙酸酯的途径。
• Oxidation of styrene derivatives by peroxydisulfate(2-) ion-copper(II) in acetic acid and acetonitrile. Reaction paths in oxidations via radical cations
  作者：Cheves Walling、Gamil M. El-Taliawi、Kalyani Amarnath

  DOI：10.1021/ja00336a043

  日期：1984.11
• Forst; Zincke, Justus Liebigs Annalen der Chemie, 1876, vol. 182, p. 262
  作者：Forst、Zincke

  DOI：——

  日期：——
• Metal-Free, Organocatalytic <i>Syn</i> Diacetoxylation of Alkenes
  作者：Wenhe Zhong、Shan Liu、Jun Yang、Xiangbao Meng、Zhongjun Li

  DOI：10.1021/ol301311e

  日期：2012.7.6

  A novel method for the organocatalytic syn diacetoxylation of alkenes has been developed using aryl iodides as efficient catalysts. A broad range of substrates, including electron-rich as well as electron-deficient alkenes, are smoothly transformed by the new procedure, furnishing the desired products in good to excellent yields with high diastereoselectivity (up to >19:1 dr).