1-phenylethane-1,2-diyl dibenzoate | 7717-61-5

• 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: 1-phenylethane-1,2-diyl dibenzoate
• 英文别名: (2-Benzoyloxy-2-phenylethyl) benzoate
• CAS: 7717-61-5
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: IIHDGRORXFWVCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  苯基乙二醇 以5%的产率得到
  参考文献：
  名称：

  MITSUNOBU O.; KIMURA J.; IIIZUMI K.; YANAGIDA N., BULL. CHEM. SOC. JAP. , 1976, 49, NO 2, 510-513

  摘要：

  DOI：

文献信息

• Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
  作者：Yuchao Lu、Chenxi Hou、Jingli Ren、Xiaoting Xin、Hengfu Xu、Yuxin Pei、Hai Dong、Zhichao Pei

  DOI：10.3390/molecules21050641

  日期：——

  A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly

  已经开发出一种新型的无金属有机碱催化的二醇和碳水化合物的区域选择性苯甲酰化。用 1.1 当量处理二醇和碳水化合物底物。1-苯甲酰咪唑和 0.2 当量。1,8-二氮杂双环[5.4.0] undec-7-ene (DBU) 在温和条件下在 MeCN 中的反应导致伯羟基的高度区域选择性苯甲酰化。重要的是，与最常用的伯羟基保护基团相比，苯甲酰基保护基团提供了一种新的保护策略。
• Dialkyl acylphosphonates: a new acylating agent of alcohols
  作者：Mitsuo Sekine、Akiko Kume、Tsujiaki Hata

  DOI：10.1016/s0040-4039(01)81975-4

  日期：1981.1

  Diethyl benzoylphosphonate (1) underwent facile benzoylation of alcohols in the presence of DBU. Reactions of diols containing primary and secondary hydroxyl groups with 1 gave predominantly monobenzoates in which primary hydroxyl groups were highly selectively benzoylated. Related acylations were also described.

  在DBU存在下，苯甲酸二乙酯二乙酯（1）进行了醇的轻松苯甲酰化。含有伯羟基和仲羟基的二醇与1的反应主要产生一苯甲酸酯，其中伯羟基被高度选择性地苯甲酰化。还描述了相关的酰化作用。
• Reactions of thallium(I) carboxylates and iodine with alkenes
  作者：Richard C. Cambie、Rodney C. Hayward、John L. Roberts、Peter S. Rutledge

  DOI：10.1039/p19740001858

  日期：——

  Treatment of an alkene with a thallium(I) carboxylate and iodine gives the corresponding vic-iodocarboxylate in high yield. The reactions are regiospecific and in conjunction with solvolysis of the products, offer an alternative to the Prévost reaction. Differences in the behaviour of thallium(I) carboxylates and silver carboxylates towards alkenes in the presence of iodine are discussed.

  用铊（烯烃的治疗我）羧酸酯和碘给出了相应的VIC以高收率-iodocarboxylate。该反应是区域特异性的，并与产物的溶剂分解结合，提供了Prévost反应的替代方法。讨论了在碘存在下of （I）羧酸盐和羧酸银对烯烃的行为差异。
• Geminal Difunctionalization of Vinylarenes: Concise Synthesis of 1,3-Dioxolan-4-ones
  作者：Pandur Venkatesan Balaji、Srinivasan Chandrasekaran

  DOI：10.1055/s-0039-1690250

  日期：2019.12

  We report a straightforward method for the synthesis of five-membered 1,3-dioxolan-4-ones by an unprecedented oxidative alkene geminal difunctionalization strategy using α-hydroxy carboxylic acids. Under the geminal oxidative addition conditions, various substituted α-hydroxy carboxylic acids and styrenes containing a variety of substituents, including β-substituted styrenes, were effectively coupled

  我们报告了一种使用 α-羟基羧酸通过前所未有的氧化烯烃双官能化策略合成五元 1,3-dioxolan-4-ones 的简单方法。在孪生氧化加成条件下，各种取代的α-羟基羧酸和含有多种取代基的苯乙烯，包括β-取代的苯乙烯，与异丁基取代的手性α-羟基羧酸有效地区域选择性偶联（反马尔科夫尼科夫），提供具有优异非对映选择性的环化。氘标记和对照研究证实了半频哪醇重排中的芳基迁移导致 α-羟基羧酸的成对氧化加成。
• Stereoselective and Stereospecific Reactions. III. Benzoylation, Cyclfzation, and Epimerization of Diols
  作者：Oyo Mitsunobu、Junji Kimura、Ken-ichi Iiizumi、Noboru Yanagida

  DOI：10.1246/bcsj.49.510

  日期：1976.2

  The benzoylation of various classes of diols by means of diethyl azodicarboxylate (1) and triphenylphosphine (2) was carried out at room temperature. When primary–secondary diols were treated with an equimolar amount of benzoic acid (3) in the presence of 1.5 molar equivalents of 1 and 2, reaction mainly Occurred at their primary hydroxyl functions. Secondary–secondary diols gave mono- and dibenzoylated products or cyclic ethers. The course of the reactions depends on the structure of diols used. Thus, intermolecular displacement giving benzoates is a favorable process for 1,3-butanediol, 2,4-pentanediol and trans-1,2-indanediol, while 2,5-hexanediol and trans-1,2-cyclohexanediol afford the cyclized products.

  各种类二醇的苯甲酰化反应通过二乙基偶氮二羧酸酯（1）和三苯基膦（2）在室温下进行。当初级-次级二醇与等摩尔的苯甲酸（3）在1和2的1.5摩尔当量存在下反应时，反应主要发生在它们的初级羟基功能上。次级-次级二醇则产生单苯甲酸酯、双苯甲酸酯或环醚。反应的进程依赖于所使用二醇的结构。因此，对于1,3-丁二醇、2,4-戊二醇和反-1,2-茚二醇，给出苯甲酸酯的分子间取代反应是有利的，而2,5-己二醇和反-1,2-环己二醇则产生环化产物。