meso-α.α'-dibenzoyloxy-bibenzyl | 38036-63-4

• 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: meso-α.α'-dibenzoyloxy-bibenzyl
• 英文别名: [(1R,2S)-2-benzoyloxy-1,2-diphenylethyl] benzoate
• CAS: 38036-63-4；671212-53-6
• 化学式: C₂₈H₂₂O₄
• 分子量: 422.48
• InChiKey: WCKDRBAZAZDBKR-WMPKNSHKSA-N

物化性质

• 沸点：
  573.8±50.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酸苄酯 在 二叔丁基过氧化物 作用下， 生成 meso-α.α'-dibenzoyloxy-bibenzyl
  参考文献：
  名称：

  过氧化二叔丁基与苯甲醛的反应。

  摘要：

  DOI：

  10.1021/ja01190a016

文献信息

• Truncated Cinchona alkaloids as catalysts in enantioselective monobenzoylation of meso-1,2-diols
  作者：E. Peter Kündig、Alvaro Enriquez Garcia、Thierry Lomberget、Pablo Perez Garcia、Patrick Romanens

  DOI：10.1039/b808268e

  日期：——

  Readily synthesised quincorine and quincoridine derived chiral diamines efficiently catalyse the asymmetric monobenzoylation of cyclic and acyclic meso-1,2-diols.

  容易合成的喹啉和喹吖啶衍生手性二胺可高效催化环状和非环状介-1,2-二醇的不对称单苯甲酰化反应。
• Highly efficient catalytic asymmetric acylation of meso-1,2-diols with benzoyl chloride in the presence of a chirai diamine combined with Et3N
  作者：Takeshi Oriyama、Keisuke Imai、Tomohumi Sano、Takeshi Hosoya

  DOI：10.1016/s0040-4039(98)00523-1

  日期：1998.5

  Catalytic asymmetric acylation of meso-1,2-diols has been successfully performed by the reaction with benzoyl chloride in the presence of 0.5 mol% of chiral diamine derived from (S)-proline combined with a stoichiometric amount of triethylamine to give the corresponding monobenzoate with good to excellent enantioselectivities.

  在0.5摩尔％衍生自（S）-脯氨酸的手性二胺与化学计算量的三乙胺混合存在下，通过与苯甲酰氯反应成功地完成了内消旋-1,2-二醇的催化不对称酰化反应，得到了相应的单苯甲酸酯具有良好至优异的对映选择性。
• Anodic addition of hydroxy and benzoyloxy groups to stilbenes
  作者：Kikuhiko Koyama、Tatsuyoshi Ebara、Tadahiko Tani、Shigeru Tsutsumi

  DOI：10.1139/v69-406

  日期：1969.7.1

  The anodic reaction of benzoic acid in acetonitrile has been carried out in the presence of trans- and cis-stilbenes using platinum electrodes. The reaction with added trans-stilbene gave meso-hydrobenzoin dibenzoate together with threo-2-benzoyloxy-1,2-diphenylethanol. Under similar conditions, cis-stilbene also gave these products. No evidence for the isomerization of cis-stilbene to the trans-isomer during the electrolysis was found. Stereoisomeric dl-hydrobenzoin dibenzoate and erythro-2-benzoyloxy-1,2-diphenylethanol were not obtained from either stilbene. For comparison, the "wet" Prévost reaction of cis-stilbene with silver acetate and iodine was studied. These results are discussed on the basis of a stepwise oxidation mechanism which involves a cyclic 1,2-benzoxonium ion intermediate.

  在乙腈中，使用铂电极在反式和顺式的苯甲酸存在下进行了苯乙烯的阳极反应。加入反式苯乙烯的反应产生了中间体羟基苯并二苯甲酸酯和threo-2-苯甲氧基-1,2-二苯基乙醇。在类似条件下，顺式苯乙烯也产生了这些产物。在电解过程中，未发现顺式苯乙烯异构化为反式异构体的证据。通过银醋酸盐和碘的“湿”普雷沃斯特反应研究了顺式苯乙烯的比较。这些结果基于一个包含环状1,2-苯并氧离子中间体的分步氧化机制进行了讨论。未从任何苯乙烯中获得立体异构体dl-羟基苯并二苯甲酸酯和erythro-2-苯甲氧基-1,2-二苯基乙醇。
• Divergent Functionalization of Alkynes Enabled by Organic Photoredox Catalysis
  作者：David A. Nicewicz、Zhengbo Zhu、Siran Qian

  DOI：10.1055/a-2009-8279

  日期：——

  oxidative conditions is challenging, as alkynes are usually recalcitrant towards typical oxidants. Herein, we communicate a strategy for the divergent functionalization of alkynes with photoexcited acridinium organic dyes, presumably via the formation of vinyl cation radicals as key intermediates. Based on the nature of the nucleophiles, different types of difunctionalized products were obtained in moderate

  炔烃在氧化条件下的直接官能化具有挑战性，因为炔烃通常对典型的氧化剂具有顽抗性。在此，我们提出了一种用光激发吖啶有机染料对炔烃进行不同官能化的策略，大概是通过形成乙烯基阳离子自由基作为关键中间体。根据亲核试剂的性质，以中等至良好的收率获得了不同类型的双官能化产物。添加路易斯酸锂导致非对映控制发生令人惊讶的逆转。
• Asymmetric acylation of meso-diols with benzoyl halide in the presence of a chiral diamine
  作者：Takeshi Oriyama、Keisuke Imai、Takeshi Hosoya、Tomohumi Sano

  DOI：10.1016/s0040-4039(97)10558-5

  日期：1998.1

  Nonenzymatic desymmetrization of cis-1,2-cyclohexanediol by the asymmetric acylation with achiral benzoyl chloride in the presence of a chiral diamine derived from (S)-proline took place to give monobenzoate in high optical yield. (C) 1997 Elsevier Science Ltd. All rights reserved.