(3-甲基苯基)丙-2-烯酸酯 | 13633-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (3-甲基苯基)丙-2-烯酸酯
• 英文名称: acrylic acid m-tolyl ester
• 英文别名: Acrylsaeure-<3-methyl-phenylester>；Acrylsaeure-m-tolylester；3-Methylphenyl prop-2-enoate；(3-methylphenyl) prop-2-enoate
• CAS: 13633-85-7
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: LPSGUCOEDCVQHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：

  (3-甲基苯基)丙-2-烯酸酯 、 苯甲醛 在 三乙烯二胺 作用下， 反应 36.0h， 以54%的产率得到3-phenyl-3-hydroxy-2-methylene-propanoic acid m-methylphenyl ester
  参考文献：
  名称：

  The ‘Baylis - Hillman Reaction’ mechanism and applications revisited

  摘要：

  It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.

  DOI：

  10.1016/s0040-4020(01)88227-2
• 作为产物：
  描述：

  2-acetoxy-propionic acid m-tolyl ester 在 pyrex tube 作用下， 生成 (3-甲基苯基)丙-2-烯酸酯
  参考文献：
  名称：

  Preparation of Aryl Acrylates and Methacrylates by Pyrolysis of the Corresponding Acetoxy Esters

  摘要：

  DOI：

  10.1021/ja01158a050

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。
• How Much Does the Hybridization of a Carbon Atom Affect the Transmission of the Substituent Effect on the Chemical Shift?
  作者：Eun Jeong Jeong、In-Sook Han Lee

  DOI：10.1002/bkcs.10067

  日期：2015.1

  systematically examined to find out the substituent effect on the chemical shift. The values of the chemical shift of the carbonyl carbon showed an inverse correlation with the Hammett σ values, and the magnitude of the slope was the largest with the propiolates. The α carbons of acrylates and propiolates also showed an inverse correlation with much smaller values of the slopes than those of the carbonyl carbons;

  1 H和13系统检查了丙酸，丙烯酸和丙酸的芳基酯的13 C NMR光谱，以了解取代基对化学位移的影响。羰基碳的化学位移值与Hammettσ值呈反比关系，且斜率的大小与丙酸酯的比值最大。丙烯酸酯和丙酸酯的α碳也显示出负相关，其斜率值比羰基碳小得多。但是那些丙酸的人绝对没有关联。但是，丙烯酸酯和丙酸酯的β碳与较大的斜率值呈正相关。斜率的符号和大小可以通过取代基电子效应通过键和空间的传递来理解。苯环的13 C化学位移值。
• 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。
• Rh(III)-catalyzed regioselective versatile indole derivatization: delivering potential of rare β-(1H-Indol-2-yl)-β-amino acids in one pot
  作者：Shuaizhong Zhang、Jinquan Zhang、Hongbin Zou

  DOI：10.1039/d3cc01289a

  日期：——

  Rh-catalyzed selective C–H functionalization of indole with two transformation routes were developed: an alkenylation–annulation with addition of KHSO4 and alkenylation–elimination in the presence of CsOAc to the corresponding products, respectively....

  Rh催化剂选择性地对吲哚进行C-H官能团化反应，有两种转化途径：分别是加入KHSO4的烯丙基化-环化反应和在CsOAc存在下的烯丙基化-消除反应，得到相应的产物。