(Z)-ethyl 3-(m-tolyl)acrylate | 874990-35-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 3-(m-tolyl)acrylate
• 英文别名: ethyl (Z)-3-(3-methylphenyl)prop-2-enoate
• CAS: 874990-35-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QQRJPDCUZPIHFK-FPLPWBNLSA-N

物化性质

• 沸点：
  287.8±9.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (Z)-ethyl 3-(m-tolyl)acrylate 在 palladium on activated charcoal 盐酸 、 三氯化铝 、 草酰氯 、 1-氯乙基氯甲酸酯 、 potassium tert-butylate 、 氢气 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 (3aR,8S,8aR)-5,8-Dimethyl-1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrrole
  参考文献：
  名称：

  The design and synthesis of a tricyclic single-nitrogen scaffold that serves as a 5-HT2C receptor agonist

  摘要：

  5-HT2C agonists have shown efficacy in limiting food consumption and thus may serve as an important drug class in combating obesity. We describe the design and synthesis of a novel tricyclic single-nitrogen scaffold that was used to produce 5-HT2C agonists. SAR was developed around this chemotype and compounds were identified that were potent (K-i < 15 nM) and selective relative to other 5-HT2 receptors. The most promising compound displayed a good pharmacokinetic profile in multiple animal species, and was efficacious in an acute feeding study in rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.070
• 作为产物：
  描述：

  3-甲基苯甲醛 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以94%的产率得到(Z)-ethyl 3-(m-tolyl)acrylate
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• Update: An Efficient Synthesis of Poly(ethylene glycol)-Supported Iron(II) Porphyrin Using a Click Reaction and its Application for the Catalytic Olefination of Aldehydes
  作者：Tamilselvi Chinnusamy、Valentin Rodionov、Fritz E. Kühn、Oliver Reiser

  DOI：10.1002/adsc.201100289

  日期：2012.6.18

  The facile synthesis of polyethylene glycol (PEG)‐immobilized iron(II) porphyrin using a copper‐catalyzed azide‐alkyne [3+2] cycloaddition “click” reaction is reported. The prepared complex 5 (PEG‐C51H39FeN7O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine, and afforded excellent olefin yields with high

  据报道，使用铜催化的叠氮化物-炔烃[3 + 2]环加成“点击”反应可轻松合成聚乙二醇（PEG）固定的铁（II）卟啉。发现制备的配合物5（PEG-C 51 H 39 FeN 7 O）是在三苯基膦存在下用重氮乙酸乙酯选择性将醛选择性烯烃化的有效催化剂，并具有高（E）选择性的优异烯烃收率。PEG负载的催化剂5易于通过沉淀和过滤回收，并循环运行十次而没有明显的活性损失。
• Retraction: An Efficient Synthesis of Poly(ethylene glycol)-Supported Iron(II) Porphyrin using a Click Reaction and its Application for the Catalytic Olefination of Aldehydes
  作者：Suman L. Jain、Jomy K. Joseph、Fritz E. Kühn、Oliver Reiser

  DOI：10.1002/adsc.200800361

  日期：2009.1

  iron(II) porphyrin using a copper-catalyzed azide-alkyne [3+2] cycloaddition is reported. In contrast to the existing methods for the synthesis of PEG-immobilized metalloporphyrins, the click method offers better catalyst loading under comparatively mild reaction conditions. The prepared complex 5 (PEG-C51H39FeN7O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl

  据报道，使用铜催化的叠氮化物-炔烃[3 + 2]环加成法成功地成功合成了聚乙二醇（PEG）固定化的铁（II）卟啉。与合成PEG固定的金属卟啉的现有方法相反，点击法在相对温和的反应条件下提供了更好的催化剂负载量。发现所制备的配合物5（PEG-C 51 H 39 FeN 7 O）是在三苯基膦存在下用重氮乙酸乙酯将醛选择性烯烃化的有效催化剂，并提供了具有高（E）选择性的优异烯烃收率。PEG负载的催化剂5 通过沉淀和过滤可以很容易地将其回收，并且可以循环使用多达十次，而不会明显损失活性。
• A graphene/hemin hybrid material as an efficient green catalyst for stereoselective olefination of aldehydes
  作者：Chetan Joshi、Pawan Kumar、Babita Behera、Alexandre Barras、Sabine Szunerits、Rabah Boukherroub、Suman L. Jain

  DOI：10.1039/c5ra19466k

  日期：——

  A hemin/graphene composite was investigated for olefination of aldehydes using ethyl diazoacetate in the presence of triphenylphosphine.

  对乙酰基二氧化碳酯在三苯基膦存在下，通过使用半胱/石墨烯复合物对醛进行烯丙基化进行了研究。
• Efficient photocatalytic chemoselective and stereoselective C–C bond formation over AuPd@N-rich carbon nitride
  作者：Heyan Jiang、Jie Xu、Sishi Zhang、Hongmei Cheng、Cuicui Zang、Fengxia Bian

  DOI：10.1039/d0cy01881c

  日期：——

  Heterogeneous chemoselective or stereoselective C–C coupling reactions remain extremely challenging in traditional organic synthesis. Here, we constructed a AuPd@N-rich carbon nitride (NRCN) photocatalyst through simple ammonia solution heat treatment of carbon nitride and then AuPd NP loading. AuPd@NRCN exhibited extraordinary light color promoted catalytic performance in C–C bond formation under

  在传统的有机合成中，异构的化学选择性或立体选择性C–C偶联反应仍然极具挑战性。在这里，我们通过对氮化碳进行简单的氨溶液热处理，然后进行AuPd NP负载，构建了一个富AuPd @ N的氮化碳（NRCN）光催化剂。AuPd @ NRCN在可见光下，在空气中的C–C键形成中表现出非凡的浅色促进催化性能。令人惊讶地，通过改变光源颜色，可以实现对不对称乌尔曼联芳基产物的高化学选择性和对Z型Heck反应产物的令人满意的立体选择性。各种底物在经济上合成不对称联芳基产物和Z具有巨大潜力型烯烃。首先通过原位验证了有效的可见光促进了C–I键活化，同时提高了AuPd @ NRCN的光催化偶联反应效率水滴。考虑到Ullmann交叉偶联反应是一个多光子反应，使用不同颜色的光源组合在Ullmann交叉偶联反应中提高的光催化性能可能是由于不同基质的激活和/或需要不同步骤的步骤引起的。能量，并且两种能量源的组合有利于提
• Preparation of a Nafion–Teflon bimembrane-supported palladium catalyst and its use in the Heck reaction
  作者：Yangzhou Li、Zhiming Li、Feng Li、Quanrui Wang、Fenggang Tao

  DOI：10.1016/j.tetlet.2005.06.091

  日期：2005.9

  A novel palladium catalyst supported on the Nafion membrane, reinforced with poly(tetrafluoroethylene) fiber, has been prepared. The catalyst exhibits high activity and stability in the Heck arylation reactions of aryl iodides with olefins and Sonogashira couplings with phenylacetylene, and can be readily recovered and reused twenty times without significant loss of activity.

  制备了负载在Nafion膜上并用聚四氟乙烯纤维增强的新型钯催化剂。该催化剂在芳基碘化物与烯烃的Heck芳基化反应以及与苯基乙炔的Sonogashira偶联中表现出高的活性和稳定性，并且可以容易地回收和重复使用二十次而不会显着降低活性。