methyl 2,4-dichlorocinnamate | 42174-01-6

• 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 2,4-dichlorocinnamate
• 英文别名: 2,4-Dichlorzimtsaeure-methylester；3-(2,4-Dichloro-phenyl)-acrylic acid methyl ester；methyl 3-(2,4-dichlorophenyl)prop-2-enoate
• CAS: 42174-01-6
• 化学式: C₁₀H₈Cl₂O₂
• mdl: MFCD18432218
• 分子量: 231.078
• InChiKey: RVBQSTISRBKZTG-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  326.6±27.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 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：

  methyl 2,4-dichlorocinnamate 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 21.09h， 生成 Methyl 4-[3-(2,4-dichlorophenyl)propylsulfanyl]-3-oxobutanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 dimsyl sodium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.5h， 生成 methyl 2,4-dichlorocinnamate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• Hydrogen Peroxide Promoted Mizoroki–Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes
  作者：Roman Lasch、Stefanie K. Fehler、Markus R. Heinrich

  DOI：10.1021/acs.orglett.6b00449

  日期：2016.4.1

  generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium–silver(I) system.

  Mizoroki-Heck反应，对于芳基重氮盐是众所周知的，最近已针对芳基肼进行了描述，现已扩展到苯基二氮烯。由偶氮羧酸盐原位生成苯基二氮杂苯，允许在乙酸银（I）或过氧化氢作为氧化剂的情况下，使用乙酸钯（II）与苯乙烯，丙烯酸酯和丙烯酰胺进行清洁，选择性的反应。因此，过氧化氢被证明是已建立的钯-银（I）系统的廉价且广泛适用的替代品。
• Synthesis and antibacterial evaluation of novel 11- O -aralkylcarbamoyl-3- O -descladinosylclarithromycin derivatives
  作者：Li Jia、Yinhu Wang、Yanxia Wang、Yinhui Qin、Chaoyu Hu、Juzheng Sheng、Shutao Ma

  DOI：10.1016/j.bmcl.2018.06.006

  日期：2018.8

  A series of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed potent activity against erythromycin-susceptible S. pyogenes, erythromycin-resistant S. pneumoniae A22072 expressing the mef gene and S. pneumoniae AB11 expressing

  设计，合成并评价了一系列新颖的11 - O-芳烷基氨基甲酰基-3 - O-去cladinosylclarithromycin衍生物的体外抗菌活性。结果表明，大多数目标化合物对易感红霉素的化脓性链球菌，表达mef基因的抗红霉素的肺炎链球菌A22072和表达mef和erm基因的肺炎链球菌AB11均显示出有效的活性。此外，大多数目标化合物对易受红霉素影响的金黄色葡萄球菌ATCC25923和枯草芽孢杆菌均显示中等活性。ATCC9372。尤其是，发现化合物11a，11b，11c，11e，11f和11h对易感红霉素的化脓性链球菌具有有利的抗菌活性，MIC值为0.015-0.125μg/ mL。此外，化合物10e，11a，11b和11c对于抗红霉素的肺炎链球菌A22072表现出优异的活性，MIC值为0.25-0.5μg/ mL。此外，化合物11c对所有抗红霉素的肺炎链球菌最有效 菌株（A22072，B1
• DMF-Catalyzed Direct and Regioselective C-H Functionalization: Electrophilic/Nucleophilic 4-Halogenation of 3-Oxypyr­azoles
  作者：Yuanyuan Liu、Guangke He、Kai Chen、Yin Jin、Yufeng Li、Hongjun Zhu

  DOI：10.1002/ejoc.201100571

  日期：2011.9

  A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl– as the key

  在催化 N,N-二甲基甲酰胺 (DMF) 存在下，在沸腾的亚硫酰氯 (SOCl2) 中开发了一种新颖、直接且高度区域选择性的 3-羟基吡唑衍生物 4-氯化。该反应可能通过 DMF 催化的亲电/亲核氯化机制进行，并涉及 SOCl2 的亲电攻击和 Cl- 的亲核取代作为关键步骤。基于这种机理，通过分别向反应体系中加入 Br- 和 I-， 3-羟基吡唑类的相应 4-溴化和 4-碘化也得到了很好的收率。这种卤化方法可以快速访问许多原始的 4-halo-3-oxypyrazole 系列。
• Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives
  作者：Xian-Qing Deng、Li-Na Quan、Ming-Xia Song、Cheng-Xi Wei、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2011.04.020

  日期：2011.7

  Herein, we described the syntheses and anticonvulsant activities of 7-(substituted-phenyl)-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones (1a–1o) and their derivatives. Most of the synthesized compounds exhibited potent anticonvulsant activities in the maximal electroshock test (MES). The most promising compound 1i showed significant anticonvulsant activity in MES test with ED50 value of 19

  在这里，我们描述了7-（取代的苯基）-6,7-二氢-[1,2,4]三唑[1,5 - a ]嘧啶-5（4 H）-ones（1a – 1o）及其派生词。大多数合成的化合物在最大电击试验（MES）中均显示出强大的抗惊厥活性。最有希望的化合物1i在MES测试中显示出显着的抗惊厥活性，ED 50值为19.7 mg / kg。它显示出很大的安全性，保护指数远高于标准药物。此外，化合物1i的效力在化学诱导的癫痫发作试验中，针对由戊四唑，异烟肼，硫代氨基脲，3-巯基丙酸和Bi​​cuculline引起的癫痫发作表明，化合物1i在几种模型中均具有广谱活性，并且可能具有多种作用机制，包括抑制电压-门控离子通道和调节GABA能活性。
• Well-Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β-Borylation and One-Pot Metathesis-Asymmetric β-Borylation Reactions
  作者：Anupam Jana、Damian Trzybiński、Krzysztof Woźniak、Karol Grela

  DOI：10.1002/chem.201704335

  日期：2018.1.19

  Highly stereoselective conjugate β‐borylation, using a new chiral NHC‐based copper catalyst, has been achieved. The chiral NHC copper complex was prepared in gram scale and showed high enantioselectivity and activity (up to 10 000 turnovers at 100 ppm of catalyst loading). This method was employed in the synthesis of a chiral β‐borylated ester from simple unconjugated alkenes though an unprecedented

  使用一种新的基于NHC的手性铜催化剂，已经实现了高度立体选择性的共轭β-硼化。手性NHC铜络合物以克为单位制备，并显示出高的对映选择性和活性（在100 ppm的催化剂负载量下，达到了1万次转换）。通过空前的一锅通复分解-不对称硼化序列，该方法被用于由简单的非共轭烯烃合成手性β-硼化酯。