methyl 2-cyano-3-(3-fluorophenyl)-2-propenoate | 62985-28-8

• 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-fluorophenyl)-2-propenoate
• 英文别名: Methyl 2-cyano-3-(3-fluorophenyl)prop-2-enoate
• CAS: 62985-28-8
• 化学式: C₁₁H₈FNO₂
• mdl: MFCD01329254
• 分子量: 205.188
• InChiKey: XNBTUEPNFFWRHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 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：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-cyano-3-(3-fluorophenyl)-2-propenoate 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 1.25h， 生成 3-(3-fluorophenyl)-3-(4-fluorophenyl)-3-cyanopropanoic acid
  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：

  氰乙酸甲酯 、 3-氟苯甲醛 生成 methyl 2-cyano-3-(3-fluorophenyl)-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

• Chemoselective phosphine-catalyzed cascade annulations between two different activated alkenes: highly diastereoselective syntheses of polysubstituted cyclohexanes and cyclopentenes
  作者：Lingchao Cai、Bo Zhang、Guiping Wu、Haibin Song、Zhengjie He

  DOI：10.1039/c0cc02817g

  日期：——

  Chemoselective phosphine-catalyzed cascade [2 + 2 + 2] and [2 + 2 + 1] annulations between two molecules of 2-arylmethylidene cyanoacetates or malononitriles and one molecule of α,β-unsaturated ketones have been developed. Under the nucleophilic catalysis of PPh3 or PBu3 (10 mol%), a highly diastereoselective synthesis of polysubstituted cyclohexanes or cyclopentenes has been successfully achieved, respectively.

  化学选择性的膦催化级联[2 + 2 + 2]和[2 + 2 + 1]环化反应已经开发出来，这些反应涉及两分子2-芳甲亚基氰乙酸酯或丙二腈与一分子的α,β-不饱和酮。在PPh3或PBu3（10 mol%）的亲核催化下，分别成功实现了高度对映选择性的多取代环己烷或环戊烯的合成。
• COPOLYMER AND OPTICAL FILM USING SAME
  申请人：Tosoh Corporation

  公开号：EP3553097A1

  公开（公告）日：2019-10-16

  Provided are a novel copolymer which is expected to form an optical film that has excellent retardation characteristics such as high retardation even in a thin film and an optical film using the same. A copolymer comprising a residue unit A represented by the general formula (1) and a residue unit B represented by the general formula (2): wherein R1 and R2 each independently represent hydrogen (provided that the case where R1 and R2 are both hydrogen is eliminated), a cyano group, an ester group (-C(=O)OX1), an amide group (-C(=O)N(X2)(X3)), or an acyl group (-C(=O)X4) (where X1 to X3 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, and X4 represents a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms); R3 to R7 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a halogen, a hydroxy group, a carboxy group, a nitro group, a cyano group, an alkoxy group (-OX5), an ester group (-C(=O)OX6), an amide group (-C(=O)N(X7)(X8)), an acyl group (-C(=O)X9), an amino group (-N(X10)(X11)), or a sulfonic acid group (-SOOX12) (where X5 to X8 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, X9 to X12 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms); and adjacent substituents among R3 to R7 may form a fused ring structure each other, wherein R8 represents an m-membered heterocyclic residue containing one or more heteroatoms or a 5-membered or 6-membered ring residue containing no heteroatom (provided that, when R8 is a 6-membered ring residue containing no heteroatom, at least one of R3 to R7 in the general formula (1) represents a hydroxy group), and m represents an integer of 5 to 10; and the m-membered heterocyclic residue, the 5-membered ring residue, and the 6-membered ring residue may form a fused ring structure.

  本发明提供了一种新型共聚物，该共聚物可望形成一种光学薄膜，该光学薄膜具有优异的延缓特性，例如即使在薄膜中也具有高延缓性，本发明还提供了使用该共聚物的光学薄膜。 由通式（1）表示的残留单元 A 和通式（2）表示的残留单元 B 组成的共聚物： 其中 R1 和 R2 各自独立地代表氢（前提是排除 R1 和 R2 都是氢的情况）、氰基、酯基（-C(＝O)OX1）、酰胺基（-C(＝O)N(X2)(X3)）或酰基（-C(＝O)X4）（其中 X1 至 X3 各自独立地代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基，而 X4 代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 14 个碳原子的环状基团）；R3 至 R7 各自独立地代表氢、具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基、具有 3 至 14 个碳原子的环基、卤素羟基、羧基、硝基、氰基、烷氧基 (-OX5)、酯基 (-C(=O)OX6)、酰胺基 (-C(=O)N(X7)(X8))、酰基 (-C(=O)X9)、氨基 (-N(X10)(X11))、或磺酸基（-SOOX12）（其中 X5 至 X8 各自独立地代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基，X9 至 X12 各自独立地代表氢、具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基）；R3 至 R7 中的相邻取代基可相互形成融合环结构、 其中 R8 代表含有一个或多个杂原子的 m 元杂环残基或不含杂原子的 5 元或 6 元环残基（条件是，当 R8 是不含杂原子的 6 元环残基时，通式（1）中 R3 至 R7 中至少有一个代表羟基），且 m 代表 5 至 10 的整数；且 m 元杂环残基、5 元环残基和 6 元环残基可形成融合环结构。
• Copolymer and optical film using same
  申请人：TOSOH CORPORATION

  公开号：US11225540B2

  公开（公告）日：2022-01-18

  A novel copolymer suitable for an optical film which is excellent in optical characteristics and has high retardation even in a thin film state, and an optical film containing the same are provided. A copolymer excellent in optical characteristics and easy to form a composite with a different polymer, and an optical film composed of the same are also provided.

  本发明提供了一种适用于光学薄膜的新型共聚物，这种共聚物具有优异的光学特性，即使在薄膜状态下也具有较高的延缓性，本发明还提供了一种含有这种共聚物的光学薄膜。此外，还提供了一种光学特性优异且易于与其他聚合物形成复合材料的共聚物，以及由其构成的光学薄膜。
• 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.