methyl (2Z)-2-(bromomethyl)-3-(4-isopropylphenyl)prop-2-enoate | 137104-40-6

• 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: methyl (2Z)-2-(bromomethyl)-3-(4-isopropylphenyl)prop-2-enoate
• 英文别名: methyl (Z)-2-(bromomethyl)-3-(4-isopropylphenyl)prop-2-enoate；(Z)-methyl 2-(bromomethyl)-3-(4-isopropylphenyl)acrylate；methyl (Z)-2-(bromomethyl)-3-(4-propan-2-ylphenyl)prop-2-enoate
• CAS: 137104-40-6
• 化学式: C₁₄H₁₇BrO₂
• 分子量: 297.192
• InChiKey: QPWGDJGSIIJHAG-MDWZMJQESA-N

物化性质

• 沸点：
  346.6±30.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  methyl (2Z)-2-(bromomethyl)-3-(4-isopropylphenyl)prop-2-enoate 在 氢氧化钾 、 水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.0h， 生成 (E)-3-(4-Isopropyl-phenyl)-2-phenoxymethyl-acrylic acid
  参考文献：
  名称：

  A new protocol for the syntheses of (E)-3-benzylidenechroman-4-ones: a simple synthesis of the methyl ether of bonducellin

  摘要：

  本文介绍了利用 3-芳基-3-羟基-2-亚甲基丙酸甲酯、丙烯酸甲酯衍生的 Baylis-Hillman 加合物合成 (E)-3-benzylidenechroman-4-ones 的简单新方法，以及应用该方法合成重要天然产物邦杜塞林的甲醚和抗真菌剂 3-(4-甲氧基亚苄基)-6-甲氧基苯并二氢吡喃-4-酮。

  DOI：

  10.1039/a804796k
• 作为产物：
  描述：

  4-异丙基苯甲醛 在 三乙烯二胺 、 硫酸 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 生成 methyl (2Z)-2-(bromomethyl)-3-(4-isopropylphenyl)prop-2-enoate
  参考文献：
  名称：

  Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer

  摘要：

  A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of the synthesized compounds were characterized by H-1, C-13 NMR, and MS; and their antifungal activity were evaluated against Alternaria solani Sorauer. These antifungal data were subjected to a quantitative structure-activity relationship (QSAR) analysis using Codessa software on the basis of the results from B3LYP/6-31G(d,p) quantum calculations. The best regressive model revealed that potentially more active compounds should have low dipole moments and Q(C-min) (minimal net atomic charge for a C atom), and high Q(O-max) (maximal net atomic charge for an O atom) and Q(N-min) (minimal net atomic charge for an N atom). The most potent compound 7k could lead to intracellular accumulation of reactive oxygen species, dissipation of mitochondrial transmembrane potential, and an autophagy-like cell death process in A. solani Sorauer. Taken together, these results laid the foundation for further design of improved crop-protection agents based on this hybrid scaffold. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.11.003

文献信息

• ?-Methylidene- and ?-Alkylidene-?-lactams from Nonproteinogenic Amino Acids
  作者：Rainer Buchholz、H. Martin R. Hoffmann

  DOI：10.1002/hlca.19910740608

  日期：1991.9.18

  Treatment of methyl 2-(1-hydroxyalkyl)prop-2-enoates 1 with conc. HBr solution afforded methyl (Z)-2-(bromomethyl)alk-2-enoates 2, which were transformed regioselectively into N-substituted methyl (E)-2- (aminomethyl)alk-2-enoates 3 (SN2 reaction) and into N-substituted methyl 2-(1-aminoalkyl)prop-2-enoates 4(SN2′ reaction). Regiocontrol of nucleophilic attack by amine was accomplished simply by choice

  用浓溶液处理2-（1-羟烷基）丙-2-烯酸甲酯1。用HBr溶液得到（Z）-2-（溴甲基）烷-2-烯酸甲酯2，将其区域​​选择性地转化成N-取代的甲基（E）-2-（氨甲基）烷-2-烯酸酯3（S N 2反应）并进入ñ取代的甲基2-（1-氨基烷基）丙-2- enoates 4（S ñ 2'反应）。胺对亲核性攻击的区域控制仅通过选择溶剂即可完成，S N 2反应发生在MeCN和S N中。在石油醚中进行2'反应。水解和内酰胺化分别得到β-内酰胺7和8，分别在C（3）处含有外环亚烷基和亚甲基。
• Multicomponent Cascade Assembly for Quinolinopyranpyrazole Architectures
  作者：Manickam Bakthadoss、Anthonisamy Devaraj、Damodharan Kannan

  DOI：10.1002/ejoc.201301422

  日期：2014.3

  A highly efficient, multicomponent protocol for the construction of functionalized quinolinopyranpyrazole scaffolds with high stereoselectivity has been developed through the application of a domino reaction. All the quinolinopyranpyrazoles were synthesized under solvent- and catalyst-free conditions and required no work-up or column chromatography.

  通过多米诺反应的应用，开发了一种高效、多组分的方案，用于构建具有高立体选择性的功能化喹啉并吡唑支架。所有喹啉并吡唑均在无溶剂和无催化剂条件下合成，无需后处理或柱层析。
• A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction
  作者：Manickam Bakthadoss、Varathan Vinayagam

  DOI：10.1039/c5ob01060h

  日期：——

  An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis–Hillman derivatives in good yields has been described for the first time. A highly functionalized tricyclic framework was created by forming two rings and two adjacent stereocentres through the formation of two N–C bonds, one

  首次描述了一种有效的方法，该方法利用Baylis-Hillman衍生物以高收率合成涉及分子内1,3-偶极腈氧化环加成反应的喹啉稠合三环化合物。通过以高度区域和非对映选择性的方式形成两个N–C键，一个C–C键和一个O–C键，形成两个环和两个相邻的立体中心，从而创建了高度功能化的三环骨架。
• Applications of Baylis–Hillman chemistry: enantioselective synthesis of (−)-methyl 3-aryl-2-methylene-3-(prop-2-yn-1-yloxy)propanoates via chiral leaving group strategy
  作者：Deevi Basavaiah、Nagaswamy Kumaragurubaran、Duddu S Sharada、Ravi Mallikarjuna Reddy

  DOI：10.1016/s0040-4020(01)00786-4

  日期：2001.9

  Asymmetric synthesis of (−)-methyl 3-aryl-2-methylene-3-(prop-2-yn-1-yloxy)propanoates in 25–40% enantiomeric purities via the reaction of methyl (2Z)-3-aryl-2-(bromomethyl)prop-2-enoates with prop-2-yn-1-ol in the presence of quinidine is described.

  通过（2 Z）-3-芳基甲基的反应，以25-40％对映体纯度不对称合成（-）-甲基3-芳基-2-亚甲基-3-（prop-2-yn-1-基氧基）丙酸酯描述了在奎尼丁存在下用丙-2-炔-1-醇与-2-（溴甲基）丙-2-烯酸酯。
• Intramolecular 1,3-Dipolar Nitrile Oxide Cycloaddition Using Baylis-Hillman Derivatives: Stereoselective Synthesis of Tricyclic Chromenoisoxazolines
  作者：Manickam Bakthadoss、Jayakumar Srinivasan、Raman Selvakumar

  DOI：10.1055/s-0031-1289707

  日期：2012.3

  A novel protocol for the construction of tricyclic chromenoisoxazoline frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition (INOC) reaction using Baylis-Hillman derivatives is described for the first time. The INOC reaction leads to a novel class of angularly substituted fused tricyclic chromenoisoxazolines, with the creation of two rings and two adjacent stereocenters, one of them

  首次描述了通过使用Baylis-Hillman衍生物的分子内1,3-偶极腈氧化环加成（INOC）反应构建三环苯并异恶唑啉骨架的新方案。INOC反应导致一类新的有角度取代的稠合三环铬异异唑啉，以独特的方式产生了两个环和两个相邻的立体中心，其中一个是全碳四元中心。以高度立体选择性的方式以良好的收率获得三环色异恶唑啉。 1,3-偶极一氧化氮环加成-铬异恶唑啉-立体选择性合成-三环骨架