(2-甲氧基苯基)苯甲酸甲酯 | 64421-25-6

• 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: (2-甲氧基苯基)苯甲酸甲酯
• 英文名称: 2-methoxybenzyl benzoate
• 英文别名: o-methoxybenzoyl benzoate；Benzenemethanol, 2-methoxy-, benzoate；(2-methoxyphenyl)methyl benzoate
• CAS: 64421-25-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: BZUHSQFJABFAHL-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56.5 °C
• 沸点：
  354.2±17.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)
• LogP：
  3.882 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苄氧基苯甲醇 在 吡啶 、 甲醇 、 镍 、 苯 作用下， 生成 (2-甲氧基苯基)苯甲酸甲酯
  参考文献：
  名称：

  Helferich; Mueller v. Blumencron, Chemische Berichte, 1953, vol. 86, p. 1058,1061

  摘要：

  DOI：

文献信息

• Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
  作者：Nivedita S. Mahajani、Rowan I. L. Meador、Tomas J. Smith、Sarah E. Canarelli、Arijit A. Adhikari、Jigisha P. Shah、Christopher M. Russo、Daniel R. Wallach、Kyle T. Howard、Alexandra M. Millimaci、John D. Chisholm

  DOI：10.1021/acs.joc.9b00745

  日期：2019.6.21

  Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive

  三氯乙亚氨酸酯是在温和条件下合成酯的有用试剂，不需要外源促进剂。这些条件避免了带有敏感官能团的底物发生不希望的分解，这种分解通常在使用强路易斯酸或布朗斯台德酸的情况下观察到。通过加热，这些反应已扩展为不具有给电子基团的苄基酯。这些廉价且方便的方法应在复杂基质中酯的形成中找到应用。
• Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols
  作者：Iraj Mohammadpoor-Baltork、Hamid Aliyan、Ahmad Reza Khosropour

  DOI：10.1016/s0040-4020(01)00521-x

  日期：2001.7

  Efficient acetylation and benzoylation of alcohols and phenols with acetic and benzoic anhydrides have been carried out under catalysis of bismuth(III) salts including BiCl3, Bi(TFA)3 and Bi(OTf)3. Selective acetylation and benzoylation of alcohols in the presence of phenols is an additional advantage of this procedure.

  在包括BiCl 3，Bi（TFA）3和Bi（OTf）3的铋（III）盐的催化下，已经进行了醇和酚与乙酸酐和苯甲酸酐的有效乙酰化和苯甲酰化。在酚存在下，醇的选择性乙酰化和苯甲酰化是该方法的另一个优点。
• 5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions
  作者：Nasser Iranpoor、Habib Firouzabadi、Dariush Khalili

  DOI：10.1039/c004357e

  日期：——

  3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated

  5,5'-二甲基-3,3'-偶氮异恶唑通过Mitsunobu协议，它用作新型高效的异质偶氮试剂，用于伯和仲苄醇和酚与脂肪族和芳香族羧酸的高选择性酯化。该反应对伯苄醇与仲醇，脂族醇以及酚的选择性很高。这异恶唑肼 副产物可以简单地通过过滤分离，并循环到其中 偶氮异恶唑 通过氧化。
• Copper-Catalyzed Cross-Coupling of Thiols, Alcohols, and Oxygen for the Synthesis of Esters
  作者：Seungyeon Lim、Miran Ji、Xi Wang、Chan Lee、Hye-Young Jang

  DOI：10.1002/ejoc.201403311

  日期：2015.1

  Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions

  研究了使用硫醇、醇和氧以良好产率形成各种酯的铜催化、一锅、三组分偶联反应。在易氧化的苄醇和烯丙醇存在下，硫醇被选择性氧化形成硫酮酯，硫醇酯经过简单的 S/O 交换得到酯。在温和的有氧条件下，硫醇可用作替代苯甲酰来源。
• The Thiolate-Catalyzed Intermolecular Crossed Tishchenko Reaction: Highly Chemoselective Coupling of Two Different Aromatic Aldehydes
  作者：Simon P. Curran、Stephen J. Connon

  DOI：10.1002/anie.201206343

  日期：2012.10.22

  Crossed products: Ortho‐substituted benzaldehydes react with other aromatic aldehydes in a highly selective, atom‐economical Tishchenko disproportionation (see scheme) in the presence of a readily prepared, inexpensive thiolate‐based catalyst. The methodology is of exceptionally wide scope and exhibits a high functional‐group tolerance.

  交叉产物：在现成的，廉价的基于硫醇盐的催化剂的存在下，邻位取代的苯甲醛与其他芳香族醛类发生高度选择性，原子经济的蒂申科歧化反应（参见方案）。该方法的适用范围非常广泛，并且具有很高的功能组容忍度。