methyl 2-cyano-3-(3,4-dichlorophenyl)-2-propenoate | 88704-79-4

• 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-cyano-3-(3,4-dichlorophenyl)-2-propenoate
• 英文别名: Methyl 2-cyano-3-(3,4-dichlorophenyl)prop-2-enoate
• CAS: 88704-79-4
• 化学式: C₁₁H₇Cl₂NO₂
• mdl: MFCD08776648
• 分子量: 256.088
• InChiKey: HWDDHMYLNYOSJI-UHFFFAOYSA-N

物化性质

• 沸点：
  393.522±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.392±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-cyano-3-(3,4-dichlorophenyl)-2-propenoate 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.5h， 生成 3-(3,4-dichlorophenyl)-3-(4-fluorophenyl)-propanamine
  参考文献：
  名称：

  Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups

  摘要：

  Analogues of the potent histamine H-2 agonist arpromidine, characterized by non-heterocyclic groups (phenyl, cyclo-hexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H-2 agonistic and H-1 antagonistic activity in the isolated guinea pig right atrium and ileum, respectively. In the diphenylpropylguanidine series an increase in H-2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 less-than-or-equal-to 7.75 vs pD2 = 7.15 for the unsubstituted parent compound). Compounds chlorinated at both phenyl rings were considerably less potent. Highest combined H-2 agonistic/H-1 antagonistic potency was found in the 4-fluorophenyl series. The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium. The H-1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series. Thus, aromatic rings appear not to be required for high H-2 agonistic potency but are useful for combined H-2 agonistic/H-1 antagonistic activity.

  DOI：

  10.1016/0223-5234(92)90145-q
• 作为产物：
  描述：

  3,4-二氯苯甲醛 、 氰乙酸甲酯 生成 methyl 2-cyano-3-(3,4-dichlorophenyl)-2-propenoate
  参考文献：
  名称：

  带有1,4-二氢吡啶的顺式-硝苯并吡喃类似物的合成，杀虫活性评估和晶体分析

  摘要：

  摘要X射线衍射证实，通过引入1,4-二氢吡啶将药效团（–C = C–NO 2）固定为顺式构型，设计了一系列新的乙炔吡喃类似物。晶体结构分析表明，对这些顺式-硝苯并吡喃类似物具有均共轭作用，巨大的共轭体系由1,4-二氢吡啶骨架和3位的酯基组成。初步生物测定表明，大部分目标化合物中的100毫克/分米显示出良好的杀虫活性（> 80％）3对棉蚜medicagini，而4-氟苯顺以20mg -nitenpyram模拟得到最好的活性，> 90％的死亡率/ dm 3。这些出色的杀虫活性表明，这种巨大的共轭体系导致分子与受体中氨基酸残基之间增强的π-π相互作用。对这些顺式-硝苯并吡喃类似物之一的作用方式和结构修饰的进一步研究正在进行中。 图形概要 。

  DOI：

  10.1007/s00706-012-0872-8

文献信息

• Catalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for the enantioselective synthesis of cyclopenta [b]indoles and pyrrolo[1,2-a]indoles
  作者：Fei Tian、Wu-Lin Yang、Tao Ni、Jian Zhang、Wei-Ping Deng

  DOI：10.1007/s11426-020-9854-3

  日期：2021.1

  synthons and efficient methods to synthesize chiral polycyclic indoles has been a hot topic in organic synthesis and medicinal chemistry owing to their broad applications in medicines, pesticides, and other functional molecules. Here, we disclosed novel indolyl substituted metal-allyl zwitterionic intermediates through the decarboxylation of conveniently available vinyl indoloxazolidones, which could be

  由于其在药物，农药和其他功能分子中的广泛应用，新型合成子和合成手性多环吲哚的有效方法的开发一直是有机合成和药物化学领域的热门话题。在这里，我们公开了通过方便地获得的乙烯基吲哚恶唑烷酮的脱羧作用而得到的新颖的吲哚基取代的金属-烯丙基两性离子中间体，通过阴离子离域化可以将其视为两种偶极种类。钯-π-烯丙基物种倾向于在不对称的[3 + 2]与缺电子的烯烃的加成中用作全碳的1,3-偶极子，从而提供了多取代的环戊烯[ b具有高区域选择性和立体选择性的吲哚。同时，在原位生成的C1烯醇铵不对称[3 + 2]环加成反应中，铱-π-烯丙基物种被认为是aza-1,3-偶极子，提供了具有高非对映异构体的吡咯并[1,2- a ]吲哚。和对映选择性。另外，偶极环加成可以容易地按比例放大，并且环加合物的几种合成转化被证明用于快速合成各种手性多环吲哚。
• Synthesis, evaluation of insecticidal activity, and crystal analysis of cis-nitenpyram analogs bearing 1,4-dihydropyridine
  作者：Chuanwen Sun、Tianyan Liu、Li Ding、Yanxia Chen、Wanggeng Zhang

  DOI：10.1007/s00706-012-0872-8

  日期：2013.7

  AbstractA new series of nitenpyram analogs were designed by introducing 1,4-dihydropyridine to fix the pharmacophore (–C=C–NO2) into the cis-configuration, as confirmed by X-ray diffraction. Crystal structure analysis showed that there was a homoconjugation effect on these cis-nitenpyram analogs, and a huge conjugated system comprising the 1,4-dihydropyridine scaffold and the ester group at the 3 position

  摘要X射线衍射证实，通过引入1,4-二氢吡啶将药效团（–C = C–NO 2）固定为顺式构型，设计了一系列新的乙炔吡喃类似物。晶体结构分析表明，对这些顺式-硝苯并吡喃类似物具有均共轭作用，巨大的共轭体系由1,4-二氢吡啶骨架和3位的酯基组成。初步生物测定表明，大部分目标化合物中的100毫克/分米显示出良好的杀虫活性（> 80％）3对棉蚜medicagini，而4-氟苯顺以20mg -nitenpyram模拟得到最好的活性，> 90％的死亡率/ dm 3。这些出色的杀虫活性表明，这种巨大的共轭体系导致分子与受体中氨基酸残基之间增强的π-π相互作用。对这些顺式-硝苯并吡喃类似物之一的作用方式和结构修饰的进一步研究正在进行中。 图形概要 。
• Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups
  作者：A Buschauer、A Friese-Kimmel、G Baumann、W Schunack

  DOI：10.1016/0223-5234(92)90145-q

  日期：1992.6

  Analogues of the potent histamine H-2 agonist arpromidine, characterized by non-heterocyclic groups (phenyl, cyclo-hexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H-2 agonistic and H-1 antagonistic activity in the isolated guinea pig right atrium and ileum, respectively. In the diphenylpropylguanidine series an increase in H-2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 less-than-or-equal-to 7.75 vs pD2 = 7.15 for the unsubstituted parent compound). Compounds chlorinated at both phenyl rings were considerably less potent. Highest combined H-2 agonistic/H-1 antagonistic potency was found in the 4-fluorophenyl series. The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium. The H-1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series. Thus, aromatic rings appear not to be required for high H-2 agonistic potency but are useful for combined H-2 agonistic/H-1 antagonistic activity.