(2-甲基苯基)丙-2-烯酸酯 | 13633-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (2-甲基苯基)丙-2-烯酸酯
• 英文名称: acrylic acid o-tolyl ester
• 英文别名: acrylic acid o-tolyl ester；Acrylsaeure-o-tolylester；o-Tolyl-acrylat；2-Acryloyloxy-toluol；Acrylsaeure-(2-methylphenylester)；2-Methylphenyl prop-2-enoate；(2-methylphenyl) prop-2-enoate
• CAS: 13633-84-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: GCIHZDWTJCGMDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-甲基苯基)丙-2-烯酸酯 、 邻甲酚 在 lithium hydride 作用下， 反应 1.0h， 生成 8-甲基-3,4-二氢香豆素
  参考文献：
  名称：

  An efficient synthesis of dihydrocoumarins

  摘要：

  Dihydrocoumarins are obtained in 40 to 60% yields in one step by heating acrylic esters with an excess of a phenol in the presence of base catalysts.

  DOI：

  10.1016/s0040-4039(00)91885-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 对苯二酚 作用下， 生成 (2-甲基苯基)丙-2-烯酸酯
  参考文献：
  名称：

  Pyrolysis of Lactic Acid Derivatives. Production of Phenyl and o-Tolyl Acrylate^*

  摘要：

  DOI：

  10.1021/ja01231a060

文献信息

• Acid- and Base-Switched Palladium-Catalyzed γ-C(sp³)–H Alkylation and Alkenylation of Neopentylamine
  作者：Jinquan Zhang、Shuaizhong Zhang、Hongbin Zou

  DOI：10.1021/acs.orglett.1c00903

  日期：2021.5.7

  unactivated C(sp3)–H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)–H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise

  远程未活化C（sp 3）–H的功能化和反应选择性是过渡金属催化系统开发的核心追求。在本文中，我们报道了Pd催化的γ-C（sp 3）–H-选择性烷基化和烯基化反应，其中可移动的7-氮杂吲哚为指导基团。发现在相同的单一底物上，否则在相同的反应条件下，酸和碱分别是选择性烷基化和烯基化的决定性调节剂。各种丙烯酸酯都适合形成C（sp 3）–C（sp 3）和C（sp 3）–C（sp 2）债券。烯基化方案可以进一步扩展至具有天然产物单元和α，β-不饱和酮的丙烯酸酯。烷基化和烯基化产物的初步合成操作证明了该策略在结构上多样化的脂族链延伸和官能化方面的潜力。机理实验研究表明，酸性和碱性催化转化共有相同的六元二聚体palladacycle。
• Tail‐To‐Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium‐Catalyzed Vinylic <i>sp</i> ² C−H Activation
  作者：Masafumi Kojima、Mio Sasaki、Mamoru Ito、Takanori Shibata

  DOI：10.1002/adsc.202200047

  日期：2022.5.17

  cationic Ir-catalyzed tail-to-tail dimerization of aryl acrylates starting from vinylic sp2 C−H activation, which gives industrially useful adipic acid ester derivatives in high yields. We further expanded the reaction to an enantioselective dimerization using aryl methacrylates and achieved the first example of catalytic asymmetric dimerization of acrylate derivatives.

  我们描述了从乙烯基sp 2 C-H 活化开始的阳离子 Ir 催化的丙烯酸芳基酯的尾对尾二聚反应，它以高产率提供工业上有用的己二酸酯衍生物。我们进一步将反应扩展到使用甲基丙烯酸芳基酯的对映选择性二聚，并实现了丙烯酸酯衍生物催化不对称二聚的第一个例子。
• Enantioselective synthesis of γ-tetrasubstituted nitrosulfonyl carboxylates and amides via<scp>l</scp>-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1039/c4ob00344f

  日期：——

  Michael addition of α-nitrosulfones to aryl- and alkyl acrylates and acrylamides proceeds in the presence of 5–10 mol% of an amino acid derived new organocatalyst to provide γ-tetrasubstituted γ-nitro-γ-sulfonyl carboxylates and amides in excellent yields and enantioselectivities. Scale-up of the reaction to multi-grams, convenient recovery of the catalyst and its recyclability without any drop in

  在5-10 mol％氨基酸衍生的新型有机催化剂存在下，将α-硝基砜迈克尔加成到丙烯酸芳基和烷基酯和丙烯酰胺上，以优异的收率提供γ-四取代的γ-硝基-γ-磺酰基羧酸酯和酰胺。对映选择性。反应规模扩大至数克，催化剂的方便回收及其可回收性，而收率和选择性均不降低，是该方法的吸引人的特点。
• ALPHA-SUBSTITUTED ACRYLATE ESTERS, COMPOSITION CONTAINING THEREOF, AND METHOD FOR PRODUCING THOSE
  申请人：Kawamoto Takahiro

  公开号：US20130072712A1

  公开（公告）日：2013-03-21

  A method for producing α-substituted acrylate esters is provided which can be suitably used as an industrial method for producing α-substituted acrylate esters because the method does not have problems of apparatus corrosion or does not require waste detoxification and allows reaction in a short time with high yield. The method for producing an α-substituted acrylate ester includes a step of carrying out a reaction of a compound having a specific structure and an active hydrogen-containing compound under a condition where a tertiary amine and an acid and/or a salt thereof coexist.

  提供了一种生产α-取代丙烯酸酯的方法，该方法可适当用作工业生产α-取代丙烯酸酯的方法，因为该方法不存在设备腐蚀问题或不需要废物解毒，并允许在短时间内高产率反应。生产α-取代丙烯酸酯的方法包括在三级胺和酸和/或其盐共存的条件下，进行具有特定结构和含有活性氢的化合物的反应的步骤。
• Attempted novel preparation of dihydrocoumarin and coumarin; obtention of aryl acrylates and 3-chloropropionates
  作者：Jaswant R. Mahajan、Hugo C. Araújo

  DOI：10.1139/v87-035

  日期：1987.1.1

  It has been found that, contrary to the published report, there is no noticeable reaction between phenol and methyl acrylate in the presence of aluminum chloride to produce phenyl acrylate (1) and dihydrocoumarin (2). Although products having the reported spectral data can be obtained by the reaction of phenol with acrylyl chloride, these products are actually phenyl acrylate and phenyl 3-chloropropionate (4), there being detected no dihydrocoumarin. This reaction has now been extended to several substituted phenols and some naphthols. Attempts at cyclization of phenyl acrylate, phenyl 3-chloropropionate, or their mixtures have been unsuccessful.

  研究发现，与已发表的报告相反，苯酚和甲基丙烯酸酯在氯化铝存在下没有明显的反应，不能产生苯基丙烯酸酯（1）和二氢香豆素（2）。虽然通过苯酚与丙烯酰氯反应可以得到具有已报告光谱数据的产物，但事实上这些产物是苯基丙烯酸酯和苯基3-氯丙酸酯（4），没有检测到二氢香豆素。这个反应现已扩展到几种取代苯酚和一些萘酚。尝试将苯基丙烯酸酯、苯基3-氯丙酸酯或它们的混合物环化均未成功。