1-苯基-1,2-乙二醇二丙酸酯 | 13756-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-1,2-乙二醇二丙酸酯
• 英文名称: (R,S)-1-phenylethane-1,2-diol dipropionate
• 英文别名: (1,2-Dipropionyloxy-aethyl)-benzol；1-phenyl-1,2-bis-propionyloxy-ethane；(+/-)-(Phenyl-aethylen)-dipropionat；(+/-)-1.2-Dipropionyloxy-1-phenyl-aethan；1-Phenyl-1,2-bis-propionyloxy-aethan；(2-Phenyl-2-propanoyloxyethyl) propanoate
• CAS: 13756-18-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: XVAFLALVAOXSMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  157-162 °C(Press: 12 Torr)
• 密度：
  1.110 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  1-苯基-1,2-乙二醇二丙酸酯 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 (R)-1-苯基-1,2-乙二醇
  参考文献：
  名称：

  Bosetti, Aldo; Bianchi, Daniele; Cesti, Pietro, Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2395 - 2398

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙烯 、 丙酸酐 在 α,α,α-三联吡啶 、 氧气 、 palladium diacetate 、 溶剂黄146 、 联硼酸频那醇酯 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以12%的产率得到1-苯基-1,2-乙二醇二丙酸酯
  参考文献：
  名称：

  B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant

  摘要：

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.

  DOI：

  10.1021/acs.orglett.8b01806

文献信息

• Metal‐Free Electrocatalytic Diacetoxylation of Alkenes
  作者：Jef R. Vanhoof、Pieter J. De Smedt、Jan Derhaeg、Rob Ameloot、Dirk E. De Vos

  DOI：10.1002/anie.202311539

  日期：2023.12.4

  A highly efficient electrocatalytic 1,2-dioxygenation of alkenes utilizing readily available materials in ambient conditions is developed. The protocol is widely applicable to aliphatic and aromatic alkenes with excellent faradaic efficiencies and yields of up to 96 %. The versatility of the method is expanded with alkenoic acids towards lactone derivatives and with other carboxylic acids like HCOOH

  利用环境条件下容易获得的材料，开发了一种高效的烯烃电催化 1,2-双氧化反应。该方案广泛适用于脂肪族和芳香族烯烃，具有出色的法拉第效率和高达 96% 的产率。该方法的多功能性通过链烯酸扩展到内酯衍生物和其他羧酸（如 HCOOH）而得到扩展。
• Syntheses with Styrene Oxide
  作者：William S. Emerson

  DOI：10.1021/ja01220a004

  日期：1945.4
• B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant
  作者：Jiuzhong Huang、Lu Ouyang、Jianxiao Li、Jia Zheng、Wuxin Yan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.8b01806

  日期：2018.9.7

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
• Bosetti, Aldo; Bianchi, Daniele; Cesti, Pietro, Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2395 - 2398
  作者：Bosetti, Aldo、Bianchi, Daniele、Cesti, Pietro、Golini, Paolo、Spezia, Sandro

  DOI：——

  日期：——