(E)-N-methoxy-3-(3-methoxyphenyl)-N-methylacrylamide | 186191-60-6

• 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: (E)-N-methoxy-3-(3-methoxyphenyl)-N-methylacrylamide
• 英文别名: N-methoxy-3-(3-methoxyphenyl)-N-methylacrylamide；(E)-N-methoxy-3-(3-methoxyphenyl)-N-methylprop-2-enamide
• CAS: 186191-60-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: IRQNVIZPSYKEFZ-BQYQJAHWSA-N

物化性质

• 沸点：
  319.7±44.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-methoxy-3-(3-methoxyphenyl)-N-methylacrylamide 在 potassium tert-butylate 、 sodium hydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 trans-[2-(3-methoxyphenyl)cyclopropane]carboxylic acid
  参考文献：
  名称：

  Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals

  摘要：

  The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25 degrees C in four cases (CF, and OMe substituents) and at 0 and 25 degrees C in the other four cases. The rate constants at 25 degrees C ranged from 1.0 x 10(11) s(-1) (p-CH3) to 4.1 x 10(11) s(-1) (p-CF,). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's Delta D substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.

  DOI：

  10.1139/cjc-77-5-6-1123
• 作为产物：
  描述：

  3-Methoxycinnamic acid 在 氯化亚砜 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 4.0h， 生成 (E)-N-methoxy-3-(3-methoxyphenyl)-N-methylacrylamide
  参考文献：
  名称：

  [EN] ANTIDIABETIC COMPOUNDS
  [FR] COMPOSÉS ANTIDIABÉTIQUES

  摘要：

  结构式（I）的新化合物及其药用盐是G蛋白偶联受体40（GPR40）的激动剂，可能在治疗、预防和抑制由G蛋白偶联受体40介导的疾病中有用。本发明的化合物可能在治疗2型糖尿病以及与该疾病常相关的病症，包括肥胖和脂质紊乱，如混合型或糖尿病性脂质代谢异常、高脂血症、高胆固醇血症和高甘油三酯血症方面有用。

  公开号：

  WO2015119899A1

文献信息

• Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
  申请人：——

  公开号：US20040092538A1

  公开（公告）日：2004-05-13

  The present invention relates to a class of compounds represented by the Formula I 1 or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the &agr; v &bgr; 3 and/or &agr; v &bgr; 5 integrin.

  本发明涉及一类由公式I代表的化合物 1 或其药用可接受的盐，包含公式I化合物的药物组合物，以及选择性地抑制或拮抗α v β 3 和/或α v β 5 整合素的方法。
• Direct and Chemoselective Synthesis of Tertiary Difluoroketones via Weinreb Amide Homologation with a CHF₂-Carbene Equivalent
  作者：Margherita Miele、Andrea Citarella、Nicola Micale、Wolfgang Holzer、Vittorio Pace

  DOI：10.1021/acs.orglett.9b03024

  日期：2019.10.18

  Weinreb amides into difluoromethylketones with a formal nucleophilic CHF2 transfer agent is reported. Activating TMSCHF2 with potassium tert-amylate enables a convenient access to the difluorinated homologation reagent, which adds to the acylating partners. The high chemoselectivity showcased in the presence of variously multifunctionalized Weinreb amides, jointly with uniformly high yields, enables the

  据报道，Weinreb酰胺与正式的亲核CHF2转移剂同化为二氟甲基酮。用叔淀粉戊酸钾激活TMSCHF2可以方便地获得二氟同系化试剂，从而增加了酰化伙伴。在各种多功能的Weinreb酰胺的存在下展现出的高化学选择性以及均一的高收率，使得该策略可普遍适用，而无需任何假定的碳负离子稳定化元素。
• Synthesis of α,β-Unsaturated α′-Haloketones through the Chemoselective Addition of Halomethyllithiums to Weinreb Amides
  作者：Vittorio Pace、Laura Castoldi、Wolfgang Holzer

  DOI：10.1021/jo401236t

  日期：2013.8.2

  A straightforward synthesis of variously functionalized α,β-unsaturated α′-haloketones has been achieved through the chemoselective addition of halomethyllithium carbenoids to Weinreb amides at −78 °C. A comparative study employing the corresponding esters under the same reaction conditions pointed out that the instability of the tetrahedral intermediate formed from the latter is responsible for the

  通过在-78°C下将卤代甲基锂类胡萝卜素化学选择性加成到Weinreb酰胺中，已经实现了各种功能化的α，β-不饱和α'-卤代酮的直接合成。在相同的反应条件下使用相应的酯进行的比较研究指出，由后者形成的四面体中间体的不稳定性是观察到的甲醇形成的原因，而不是所需的卤代酮。
• Asymmetric synthesis of the allocolchicinoid natural product N-acetylcolchinol methyl ether (suhailamine), solid state and solution phase conformational analysis
  作者：Stephen G. Davies、Ai M. Fletcher、Paul M. Roberts、James E. Thomson、Angus Yeung

  DOI：10.1016/j.tet.2019.130694

  日期：2019.12

  An asymmetric synthesis of the allocolchicinoid N-acetylcolchinol methyl ether (NCME) from 3-methoxybenzaldehyde is reported. Comparison of 1H and 13C NMR spectroscopic data obtained for this sample of NCME provide concrete evidence for the assertion that this compound is congruous with the natural product that has been dubbed suhailamine, establishing NCME as a naturally-occurring allocolchicinoid

  据报道，由3-甲氧基苯甲醛不对称合成二十碳五烯基N-乙酰胆碱甲醚（NCME）。比较从该NCME样品获得的1 H和13 C NMR光谱数据，可以为该化合物与被称为suhailamine的天然产物相匹配的断言提供具体证据，从而确立了NCME为天然存在的二十碳五烯酸类固醇。还首次报道了NCME的单晶X射线衍射结构，表明偏爱采用（7 S，R a，Z）形式（即描述固态的联芳基轴和酰胺N–CO键的方向以及立体中心的构型）。通过一系列NMR光谱技术进行分析，揭示了DMSO- d 6溶液中相同形式的偏爱，而（7 S，R a，Z），（7 S，S在CDCl 3中观察到a，Z）和（7 S，R a，E）的形式。
• Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry
  作者：Raffaele Senatore、Laura Castoldi、Laura Ielo、Wolfgang Holzer、Vittorio Pace

  DOI：10.1021/acs.orglett.8b00896

  日期：2018.5.4

  Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization

  在此发现，二硒缩醛是先前在与α-硒酮的同源化策略中被认为是副产物的副产物，在此被认为是极好的起始原料。它们易于进行硒/锂交换，从而得到硒代碳负离子，将其平稳地添加到Weinreb酰胺中，即可通过一次化学操作化学选择性地制备α-芳基-和α-烷基硒代甲基酮。在光学纯的起始原料的存在下未观察到外消旋作用。