5-nitro-2-hydroxy-(E)-cinnamic acid methyl ester | 197314-77-5

• 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: 5-nitro-2-hydroxy-(E)-cinnamic acid methyl ester
• 英文别名: methyl (E)-3-(2-hydroxy-5-nitrophenyl)acrylate；(E)-methyl 2’-hydroxy-5’-nitrocinnamate；5-nitro-2-hydroxy-trans-cinnamic acid methyl ester；2-hydroxy-5-nitro-cinnamic acid methyl ester；5-Nitro-2-hydroxy-trans-zimtsaeure-methylester；2-Hydroxy-5-nitro-zimtsaeure-methylester；5-Nitro-cumarsaeure-methylester；methyl (E)-3-(2-hydroxy-5-nitrophenyl)prop-2-enoate
• CAS: 197314-77-5
• 化学式: C₁₀H₉NO₅
• 分子量: 223.185
• InChiKey: BNTJUGZEVVRLGY-GORDUTHDSA-N

物化性质

• 沸点：
  403.4±40.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-2-hydroxy-(E)-cinnamic acid methyl ester 750.0 ℃ 、0.67 Pa 条件下， 反应 0.08h， 以75%的产率得到6-硝基香豆素
  参考文献：
  名称：

  通过 3-（2-羟基芳基）丙烯酸酯的快速真空热解合成香豆素，1

  摘要：

  3-(2-羟基芳基)丙烯酸酯的快速真空热解以高产率得到香豆素(和其他融合的α-吡喃酮)。

  DOI：

  10.1039/a702405c
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 甲醇 作用下， 生成 5-nitro-2-hydroxy-(E)-cinnamic acid methyl ester
  参考文献：
  名称：

  A simple technique of using novel thread-holding and knot-pushing forceps for extracorporeal knot-tying

  摘要：

  We designed some novel knot-pushing forceps for extracorporeal knot-tying and describe herein our simple technique of utilizing them. These forceps are modified only by a single l-mm hole between their jaws, which hold a thread and push the knot toward the ligating tissue. The application of this simple device was handled well by surgeons beginning to perform advanced endoscopic surgery. The simple modification explained in this report seems applicable to most of the forceps currently used.

  DOI：

  10.1007/s005950070132

文献信息

• One-Pot Allylation–Intramolecular Vinylogous Michael Addition–Isomerization Cascade of <i>o</i>-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives
  作者：Battu Harish、Manyam Subbireddy、Owk Obulesu、Surisetti Suresh

  DOI：10.1021/acs.orglett.9b00414

  日期：2019.3.15

  intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular

  已经公开了导致杂环的合成的独特的分子内乙烯基乙烯基迈克尔加成。碱促进的邻位羟基肉桂酸酯或-肉桂腈或-邻苯二甲酸酯与γ-溴丁酸的一锅顺序O-烯丙基化反应，然后在分子内共轭添加乙烯基Michael供体导致高取代度的高取代苯并呋喃衍生物形成。分子内事件继之以两个[1,3] -H转变导致芳构化，似乎是这种前所未有的转化成功的关键。
• Cyclization of <i>ortho</i>-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
  作者：Florian Boeck、Max Blazejak、Markus R Anneser、Lukas Hintermann

  DOI：10.3762/bjoc.8.186

  日期：——

  (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140–250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60–70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph₃P=CHCO₂Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

  (E)-烷基ortho-羟基肉桂酸酯在140–250°C的高温下环化为香豆素。我们发现，在MeOH溶液中使用三-n-丁基膦（20 mol％）作为亲核有机催化剂，可以在更温和的条件下（60–70°C）进行环化。通过Wittig反应将ortho-羟基芳基醛与Ph₃P=CHCO₂Me反应，制备了几种香豆素，得到(E)-甲基ortho-羟基肉桂酸酯，随后进行膦催化的环化。
• Post-mao new poetry and “Occidentalism”
  作者：Xianlin Song

  DOI：10.1007/s12140-000-0005-6

  日期：2000.3

  In their attempts to come to grips with the accelerated process of reform and globalization, Chinese intellectuals, poets, and critics have employed a discursive pracetied which could be called Occidentalism, the reverse of Said's well-known Orientalism. The purpose of this essay is to examine the manifestation of this change through the discursive practices employed by post-Mao new poets of the mid-1980s in relation to their projection of Western modern and postmodern thinking. In particular, I wish to focus on the Chinese poetic transformation of certain aspects of existentialism, Structuralist linguistics and the post-structural critique of language as implemented by these poets.

  中国的知识分子、诗人和评论家在试图应对加速的改革和全球化进程时，采用了一种可称为西方主义的话语方式，这与萨义德著名的东方主义正好相反。这篇文章的目的是通过 20 世纪 80 年代中期毛泽东之后的新诗人对西方现代和后现代思想的投射所采用的话语实践来研究这种变化的表现形式。尤其是，我希望重点探讨这些诗人对存在主义、结构主义语言学和后结构语言批判的某些方面进行的中国诗学转换。
• Dey; Row, Journal of the Chemical Society, 1924, vol. 125, p. 561
  作者：Dey、Row

  DOI：——

  日期：——
• Harikrishna, G.; Hariprasad, K. Siva; Raju, B. China, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 1, p. 111 - 116
  作者：Harikrishna, G.、Hariprasad, K. Siva、Raju, B. China、Tiwari, A. K.、Zehra, A.

  DOI：——

  日期：——