3-(3,4-二甲氧基苯基)-2-硝基-2-烯酸乙酯 | 53969-89-4

• 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
• 中文名称: 3-(3,4-二甲氧基苯基)-2-硝基-2-烯酸乙酯
• 英文名称: ethyl 3-(3',4'-dimethoxyphenyl)-2-nitroacetate
• 英文别名: ethyl 3-(3,4-dimethoxyphenyl)-2-nitroacrylate；(Z/E)-ethyl 3,4-dimethoxy-α-nitrocinnamate；3.4-Dimethoxy-α-nitrozimtsaeure-ethylester；Ethyl 3-(3,4-dimethoxyphenyl)-2-nitroprop-2-enoate；ethyl 3-(3,4-dimethoxyphenyl)-2-nitroprop-2-enoate
• CAS: 53969-89-4
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: WVXCKUSHRDENDP-UHFFFAOYSA-N

物化性质

• 沸点：
  413.8±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4-二甲氧基苯基)-2-硝基-2-烯酸乙酯 、 3,4-二氢罂粟碱 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以20%的产率得到ethyl 1,2-bis(3,4-dimethoxyphenyl)-8,9-dimethoxypyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h
• 作为产物：
  描述：

  硝基乙酸乙酯 、 3,4-二甲氧基苯甲醛 在 二乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以66%的产率得到3-(3,4-二甲氧基苯基)-2-硝基-2-烯酸乙酯
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h

文献信息

• Synthesis of Lamellarin U and Lamellarin G Trimethyl Ether by Alkylation of a Deprotonated α-Aminonitrile
  作者：Johannes C. Liermann、Till Opatz

  DOI：10.1021/jo800467e

  日期：2008.6.1

  1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions

  1,2,3,4-四氢异喹啉-1-腈可以用作起始的一锅合成5,6-二氢吡咯并[2,1的材料一]异喹啉和1-苄基-3,4-二氢异喹啉。后面的化合物以短的反应顺序被转化为薄片蛋白G三甲醚和薄片蛋白U。这种方法允许引入用于酚羟基官能团的酸敏感保护基，该保护基在经典的Bischler-Napieralski反应的苛刻条件下会裂解。
• Enantioselective total synthesis of furofuran lignans <i>via</i> Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates
  作者：Can Zhao、Ijaz Khan、Yong Jian Zhang

  DOI：10.1039/d0cc05640e

  日期：——

  Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates (VECs) with 2-nitroacrylates under mild conditions. By using this asymmetric catalytic reaction as a key step, several furofuran lignans with stereodivergency have been effectively synthesized through 5- or 6-step sequences from readily available starting materials.

  本文中，已经开发了在温和条件下通过碳酸乙烯乙烯酯（VEC）与2-硝基丙烯酸酯的钯催化不对称烯丙基环加成反应，开发出具有三个立体中心的四氢呋喃的实用有效方法。通过使用该不对称催化反应作为关键步骤，已通过易于使用的起始原料通过5步或6步序列有效合成了几种具有立体分歧性的呋喃呋喃木脂素。
• A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride
  作者：Seiko Hirotani、Eisuke Kaji

  DOI：10.1016/s0040-4020(99)00119-2

  日期：1999.4

  Titanium tetrachloride-induced cyclization of 3-(o- or m-substituted p-methoxyphenyl)-2-nitro acrylates (1) provided stereoselectively (4 alpha,5 beta)-1-oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p-methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4 alpha,5 beta)-4'-oxospiro[isoxazole-(4H)5,1'(4'H)-naphthalene]. 3-(10'-methoxy-9'-anthryl)-2-nitroacrylate was converted to 10-oxospiro-[anthracene-(10H)9,5'(4'H)-isoxazole]. (C) 1999 Elsevier Science Ltd. All rights reserved.