2-fluorobenzyl benzoate | 478970-84-2

• 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: 2-fluorobenzyl benzoate
• 英文别名: (2-fluorophenyl)methyl benzoate
• CAS: 478970-84-2
• 化学式: C₁₄H₁₁FO₂
• 分子量: 230.239
• InChiKey: LNSLNEYGHIUFQC-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±17.0 °C(Predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 保留指数：
  1787

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氟苄醇 、 苯甲酰氯 在 吡啶 作用下， 反应 1.5h， 生成 2-fluorobenzyl benzoate
  参考文献：
  名称：

  Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension

  摘要：

  Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.056

文献信息

• Esterification of the Primary Benzylic C–H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation
  作者：Bing Lu、Fan Zhu、Hong-Mei Sun、Qi Shen

  DOI：10.1021/acs.orglett.7b00148

  日期：2017.3.3

  The first iron-catalyzed esterification of the primary benzylic C–H bonds with carboxylic acids using di-tert-butyl peroxide as an oxidant is achieved by novel ionic iron(III) complexes containing an imidazolinium cation. The use of well-defined, air-stable, and available iron(III) complex in a 5 mol % loading and readily available starting materials with a broad generality and outstanding sterically

  新型的含咪唑啉阳离子的离子型铁（III）络合物实现了使用过氧化二叔丁基作为氧化剂对伯苄基C–H键与羧酸进行的首次铁催化酯化反应。使用定义明确，空气稳定且可用的铁（III）配合物（负载量为5 mol％）以及易于获得的起始材料（具有广泛的通用性和出色的空间位阻性），使该方法成为常规方法中其他方法的有用替代方法用于合成苄基酯。
• DCID-mediated esterification of carboxylic acids with alcohols under mild conditions
  作者：Farzaneh Nasiri、Javad Mokhtari、Salman Taheri、Zohreh Mirjafary

  DOI：10.1039/d3ra04048h

  日期：——

  the esterification of carboxylic acids with alcohols at room temperature. The reaction represents the first DCID-promoted esterification under mild conditions with good to excellent yields. Reactions can proceed smoothly with those bearing electron-withdrawing and donating group(s) on the carboxylic acids and benzyl alcohols at ambient temperature. Furthermore, we proposed a plausible mechanism and

  DCID（二氯咪唑烷二酮） 2用作新型偶联剂，用于室温下羧酸与醇的酯化反应。该反应代表了首次 DCID 促进的酯化反应，在温和条件下实现了良好至优异的产率。羧酸和苯甲醇上带有吸电子和给电子基团的反应可以在环境温度下顺利进行。此外，我们提出了一个合理的机制，并通过分离和表征中间体3a和7来证实它。通过比较熔点和NMR谱证实了合成化合物的结构。