ethyl 2-nitro-3-(3-nitrophenyl)acrylate | 21646-75-3

• 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: ethyl 2-nitro-3-(3-nitrophenyl)acrylate
• 英文别名: α,m-Dinitro-zimtsaeureaethylester；3,α-dinitro-cinnamic acid ethyl ester；3,α-Dinitro-zimtsaeure-aethylester；Ethyl 2-nitro-3-(3-nitrophenyl)prop-2-enoate
• CAS: 21646-75-3
• 化学式: C₁₁H₁₀N₂O₆
• 分子量: 266.21
• InChiKey: BQVYGIMSZWCAAU-UHFFFAOYSA-N

物化性质

• 熔点：
  105.5-106 °C
• 沸点：
  411.7±40.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitro-3-(3-nitrophenyl)acrylate 、 苯 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  van der Lee, Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 1139

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 苯 作用下， 生成 ethyl 2-nitro-3-(3-nitrophenyl)acrylate
  参考文献：
  名称：

  van der Lee, Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 1139

  摘要：

  DOI：

文献信息

• Monofluorinated 5-membered rings <i>via</i> fluoromethylene transfer: synthesis of monofluorinated isoxazoline <i>N</i>-oxides
  作者：Arturs Sperga、Armands Kazia、Janis Veliks

  DOI：10.1039/d1ob00270h

  日期：——

  The synthesis of five-membered rings using fluoromethylene transfer chemistry is an attractive method for building fluorinated products of high value. This work demonstrates for the first time that one-fluorine-one-carbon modification of a substrate could be a viable strategy to access monofluorinated five-membered rings. The synthetic methodology was developed to access monofluorinated isoxazoline-N-oxides

  使用氟代亚甲基转移化学方法合成五元环是构建高价值氟化产物的一种有吸引力的方法。这项工作首次证明，对基材进行单氟单碳修饰可能是访问单氟化五元环的可行策略。开发了一种合成方法，可使用氟甲基s试剂从取代的2-硝基丙烯酸酯开始，一步获得单氟化异恶唑啉-N-氧化物。
• P(NMe₂)₃-Mediated Reductive (1 + 4) Annulation Reaction of Isatins with Nitroalkenes: An Access to Spirooxindolyl Isoxazoline <i>N</i>-Oxides and Their Corresponding Isoxazolines
  作者：Yiyi Liu、Hengyu Li、Xun Zhou、Zhengjie He

  DOI：10.1021/acs.joc.7b01962

  日期：2017.10.20

  The reductive (1 + 4) annulation reaction of isatins and substituted nitroalkenes mediated by a trivalent phosphorus reagent has been realized for the first time, providing easy access to spirooxindolyl isoxazoline N-oxides in moderate to excellent yields with a flexible substrate scope. This reaction presumably proceeds through a Michael addition–intramolecular substitution sequence via active in

  首次实现了由三价磷试剂介导的靛红和取代的硝基烯烃的还原（1 + 4）环化反应，可轻松获得具有中等范围至优异收率的spirooxindolyl异恶唑啉N-氧化物，并具有灵活的底物范围。该反应大概是通过从加成素和P（NMe 2）3原位产生的活性Kukhtin-Ramirez两性离子通过迈克尔加成-分子内取代序列进行的。还证明了螺氧新吲哚基异恶唑啉N-氧化物可以容易地以良好的产率转化成相应的异恶唑啉。
• Rapid Assembly of Spiroisoxazolidines by [4 + 1] Dearomative Spiroannulation of α-Bromo-β-naphthol and Nitroolefin
  作者：Mian Qi、Mengyao Li、Lu Bai、Jingjing Liu、Xinjun Luan

  DOI：10.1021/acs.joc.3c00335

  日期：2023.5.5

  A novel [4 + 1] dearomative spiroannulation of α-halo-β-naphthol and nitroolefin has been developed for the direct construction of various spiroisoxazolidines in high chemo- and diastereoselectivity. Notably, halophenols (X = Cl and I) were also tolerated by this reaction. This transformation was realized through a sequence of electrophilic dearomatization/dehalogenation, and mechanistic studies revealed

  开发了一种新型的 α-卤代-β-萘酚和硝基烯烃的 [4 + 1] 脱芳环化螺环化反应，用于以高化学选择性和非对映选择性直接构建各种螺异恶唑烷。值得注意的是，该反应也可以耐受卤酚（X = Cl 和 I）。这种转化是通过一系列亲电脱芳构化/脱卤化作用实现的，机理研究表明 C(sp 3 )–X 键断裂发生了不同的路径。此外，该方法的潜在应用通过几个进一步的转换得到了例证。
• Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism
  作者：Riccardo Rossi、L. Tauchmanovà、A. Luciano、R. Valentino、S. Savastano、C. Battista、M. Di Martino、G. Lombardi

  DOI：10.1007/bf03343881

  日期：2001.7

  The etiologic diagnosis of hirsutism is often difficult. Previous studies have reported normal basal androgen and SHBG concentrations in 33-50% of hirsute women, suggesting the presence of an "idiopathic" form of hirsutism as the most frequent cause of this problem. The recent use of GnRH-analogues together with the corticotropin stimulation test allows better understanding of whether the cause of hirsutism is androgen excess and, if so, whether the origin of the latter is ovarian, adrenal or both. The present study evaluated adrenal and ovarian function in 48 young hirsute women as well as in 78 normal women matched for body mass index and age, who acted as control group. To determine ovarian function, a single 100-mug dose of GnRH analogue triptorelin was injected sc; thereafter, gonadotropins, 17-hydroxyprogesterone (17-OHP), Delta4-androstenedione (Delta4), total testosterone (T) and estradiol were determined. To better understand the adrenal function, 250 mug of 1,24 ACTH were administrated as iv infusion for 5 h, and plasma cortisol (F), 17-OHP, Delta4, DHEAS, T, 11-desossicortisol were measured. The combined use of these two stimulation tests was able to detect mild to moderate abnormalities in the steroidogenesis of ovaries alone (23%), adrenals alone (16.6%), or both (35.4%) in most hirsute women (75%) with otherwise normal baseline androgen concentrations. In particular, patients showed significantly increased responses of 17-OHP, Delta4, total T, 11-desossicortisol, and F to 1,24-ACTH administration. Moreover, they also had significantly higher 17-OHP and T responses to triptorelin. In conclusion, milder forms of functional ovarian and/or adrenal hyperandrogenism, similar to those found in clearly hyperandrogenic women, were observed and could be an underlying mechanism of idiopathic hirsutism. (J. Endocrinol. Invest. 24: 491-498, 2001) (C) 2001, Editrice Kurtis.
• Efficient synthesis of β-nitro amides by aminocarbonylation of ethoxycarbonyl-containing nitroalkenes with carbamoylsilane
  作者：Yanhong Liu、Yuling Han、Jianxin Chen

  DOI：10.1016/j.mencom.2021.01.041

  日期：2021.1