methyl (2E)-3-(2′-amino-5′-methoxyphenyl)prop-2-enoate | 142010-18-2

• 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 (2E)-3-(2′-amino-5′-methoxyphenyl)prop-2-enoate
• 英文别名: methyl 2-amino-5-methoxycinnamate；methyl trans-5-methoxy-2-aminocinnamate；methyl (E)-3-(2-amino-5-methoxyphenyl)prop-2-enoate
• CAS: 142010-18-2
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: DDZBRWSBJMCIDH-ZZXKWVIFSA-N

物化性质

• 沸点：
  360.6±32.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(2′-amino-5′-methoxyphenyl)prop-2-enoate 在 4-polyvinylpyridine 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3,4-Tetrahydro-6-methoxy-3-(methoxycarbonyl)-2-oxo-4-quinoline acetic acid, methyl ester
  参考文献：
  名称：

  Synthesis and carbamoylation of 1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocin-8-ol: bridged analogues of physostigmine

  摘要：

  The synthesis and carbamoylation of 2,6-methano-1,3-benzodiazocin-8-ol is described. A one pot silyl-aryl ether to carbamate transformation was developed. The compounds are analogues of the cholinesterase inhibitor physostigmine.

  DOI：

  10.1016/0040-4039(92)88151-t
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲醛 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 methyl (2E)-3-(2′-amino-5′-methoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of 2-acylindole-3-acetic acids: a novel base-mediated indole synthesis

  摘要：

  An efficient and expedient synthetic route to 2-acylindole-3-acetic acids is described. This work first demonstrates a one-pot room-temperature indole ring construction via the in situ generation of indoline intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01879-3

文献信息

• 2,3-substituted indole compounds as anti-inflammatory and analgesic agents
  申请人：——

  公开号：US06608070B1

  公开（公告）日：2003-08-19

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is OH, C1-6 alkoxy, —NR2R3 or heterocycle; Q is selected from the following: (a) an optionally substituted phenyl, (b) an optionally substituted 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), (c) an optionally substituted 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, (d) an optionally substituted C3-7 cycloalkyl and (e) an optionally substituted benzo-fuzed heterocycle; R1 is hydrogen, C1-4 alkyl or halo; R2 and R3 are independently hydrogen, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy or CN; X is independently selected from H, halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino and CN; and n is 0, 1, 2, 3 and 4. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  这项发明提供了以下式的化合物： 或其药学上可接受的盐，其中Z为OH、C1-6烷氧基、—NR2R3或杂环；Q从以下中选择：(a) 可选择取代的苯基，(b) 可选择取代的含有一个、两个、三个或四个氮原子的6-成员单环芳基，(c) 可选择取代的含有O、S和N中选择的一个杂原子的5-成员单环芳基，并且除所述杂原子外还可选择含有一个、两个或三个氮原子，(d) 可选择取代的C3-7环烷基和(e) 可选择取代的苯并噻吩杂环；R1为氢、C1-4烷基或卤素；R2和R3独立地为氢、OH、C1-4烷氧基、C1-4烷基或用卤素、OH、C1-4烷氧基或CN取代的C1-4烷基；X独立地从H、卤素、C1-4烷基、卤素取代的C1-4烷基、OH、C1-4烷氧基、卤素取代的C1-4烷氧基、C1-4烷基硫醚、NO2、NH2、二-(C1-4烷基)氨基和CN中选择；n为0、1、2、3和4。 这项发明还提供了一种用于治疗前列腺素参与的医疗状况的药物组合物。
• Synthesis of 5-Amino-2,5-dihydro-1<i>H</i>-benzo[<i>b</i>]azepines Using a One-Pot Multibond Forming Process
  作者：Salaheddin A. I. Sharif、Ewen D. D. Calder、Fábio G. Delolo、Andrew Sutherland

  DOI：10.1021/acs.joc.6b01357

  日期：2016.8.5

  to allylic trichloroacetimidates bearing a 2-allylaminoaryl group from readily available 2-iodoanilines combined with a one-pot multibond forming process has allowed the efficient synthesis of a series of 5-amino-2,5-dihydro-1H-benzo[b]azepines. The potential of these compounds as synthetic building blocks was demonstrated by the preparation of a late-stage intermediate of the hyponatremia agent, mozavaptan

  从容易获得的2-碘苯胺与一锅多键形成工艺相结合，可快速获得带有2-烯丙基氨基芳基的烯丙基三氯乙酰亚氨酸酯，从而有效地合成了一系列5-氨基-2,5-二氢-1H-苯并[ b ] ze。制备低钠血症药物莫扎伐普坦的后期中间体证明了这些化合物作为合成构件的潜力。
• Bicycliccarbonyl indole compounds as anti-inflammatory/analgesic agents
  申请人：Pfizer Inc

  公开号：US06303628B1

  公开（公告）日：2001-10-16

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein A is C 1-6 alkylene or —NR1—; Z is C(═L)R2, or SO2R3; U is CH or N; W and Y are independently selected from —CH2—, O, S and —N—R1; m is 1, 2 or 3; q and r are independently 0, 1 or 2; X is independently selected from halogen, C1-4 alkyl, halo-substituted C1-4 alkyl, hydroxy, C1-4 alkoxy, halo-substituted C1-4 alkoxy or the like; n is 1 or 2; L is oxygen or sulfur; R1 is hydrogen or C1-4 alkyl; R2 is hydroxy, C1-6alkyl, halo-substituted C1-6 alkyl, C1-6 alkoxy, halo-substituted C1-6 alkoxy, C3-7 cycloalkoxy, C1-4 alkyl(C3-7 cycloalkoxy), —NR4R5 or the like; R3 is C1-6 alkyl or halo-substituted C1-6 alkyl; and R4 and R5 are independently selected from hydrogen, C1-6 alkyl and halo-substituted C1-6alkyl. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  该发明提供了以下公式的化合物：或其药学上可接受的盐，其中A是C1-6烷基或—NR1—；Z是C(═L)R2，或SO2R3；U是CH或N；W和Y分别选择自—CH2—，O，S和—N—R1；m为1、2或3；q和r独立地为0、1或2；X独立地选择自卤素，C1-4烷基，卤代C1-4烷基，羟基，C1-4烷氧基，卤代C1-4烷氧基或类似物；n为1或2；L为氧或硫；R1为氢或C1-4烷基；R2为羟基，C1-6烷基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C3-7环烷氧基，C1-4烷基(C3-7环烷氧基)，—NR4R5或类似物；R3为C1-6烷基或卤代C1-6烷基；R4和R5独立地选择自氢，C1-6烷基和卤代C1-6烷基。该发明还提供了一种药物组合物，用于治疗前列腺素作为病原体参与的医疗状况。
• Transition metal complexes in organic synthesis, part 36. Cyclization of tricarbonyliron complexes by oxygen to 4a,9a-dihydro-9H-carbazoles: Application to the synthesis of mukonine, mukonidine, and pyrido[3,2,1-jk]carbazoles
  作者：Hans-Joachim Knölker、Marcus Wolpert

  DOI：10.1016/s0040-4039(96)02364-7

  日期：1997.1

  Aryl-substituted tricarbonyl-(η4-cyclohexa-1,3-diene)iron complexes are oxidatively cyclized in protic medium in the air to tricarbonyliron-complexed 4a,9a-dihydro-9H-carbazoles. The method is applied to the total synthesis of mukonine and mukonidine.

  芳基取代的tricarbonyl-（η 4 -环己-1,3-二烯）合铁络合物在质子介质氧化环化在空中tricarbonyliron络合4a中，9A二氢-9- ħ -carbazoles。该方法适用于粘康宁和粘康定的全合成。
• Synthesis of 2-Vinylindole-3-Acetic Acid Derivatives via Cyanide-Catalyzed Imino-Stetter Reaction
  作者：Hong-Ahn Seo、Cheol-Hong Cheon

  DOI：10.1021/acs.joc.6b01621

  日期：2016.9.2

  for the synthesis of 2-vinylindole-3-acetic acid derivatives from aldimines, which are derived from 2-aminocinnamic acid derivatives and α,β-unsaturated aldehydes, via a cyanide-catalyzed imino-Stetter reaction is described. Various types of 2-aminocinnamic acid derivatives and α,β-unsaturated aldehydes could be used in this protocol, and the desired 2-vinyl substituted indole-3-acetic acid derivatives

  描述了一种新的方法，该方法通过氰化物催化的亚氨基-Stetter反应从醛亚胺合成2-乙烯基吲哚-3-乙酸衍生物，该衍生物衍生自2-氨基肉桂酸衍生物和α，β-不饱和醛。在该方案中可以使用各种类型的2-氨基肉桂酸衍生物和α，β-不饱和醛，并以高收率获得了所需的2-乙烯基取代的吲哚-3-乙酸衍生物。使用从乙醛酸酯和2-氨基肉桂酸衍生物获得的亚胺，该氰化物催化的亚氨基-Stetter反应进一步扩展到制备在2-位带有羧酸官能团的吲哚-3-乙酸衍生物。