(E)-1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene | 389838-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene
• 英文别名: (E)-1-(2-(methylthio)phenyl)-2-pyrrolidinyl-1-nitroethene；(E)-1-(2-(2-(methylthio)phenyl)-2-nitrovinyl)pyrrolidine；(E)-1-(1-pyrrolidinyl)-2-nitro-2-[2-(methylthio)phenyl]ethene；1-[(E)-2-(2-methylsulfanylphenyl)-2-nitroethenyl]pyrrolidine
• CAS: 389838-02-2
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: MWYBFOMYLMZRAU-ZRDIBKRKSA-N

物化性质

• 沸点：
  403.7±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-1-[2-(methylsulfonyl)phenyl]-1-nitro-2-(2-thienyl)ethylene
  参考文献：
  名称：

  到4- nitrothiochroman容易访问小号，小号经由环放大-dioxides从3-硝基苯并[ b ]噻吩

  摘要：

  （E）-2-芳基-1- [2-（甲硫基）苯基] -1-硝基乙烯5可以很容易地氧化成相关的砜6并在用双（三甲基甲硅烷基）锂金属化后通过分子内迈克尔加成反应有效地进行环化酰胺在THF中的溶液。用氯化铵淬灭后，以非对映异构体混合物的形式获得3-芳基-4-硝基硫代苯并二氢吡喃S 2，S-二氧化物2，收率良好至优异。闭环步骤的产率和立体化学似乎都受到3-芳基部分的空间效应的影响。由于硫化物5源自3-硝基苯并[ b ]噻吩（1），整个1到2的过程可以被认为是硫杂环的5到6个环的有效扩环。还完成了对分离的非对映异构体2的构象1 H NMR和分子力学研究。

  DOI：

  10.1016/j.tet.2004.04.039
• 作为产物：
  描述：

  四氢吡咯 、 3-硝基苯并噻吩 、 碘甲烷 在 silver nitrate 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene
  参考文献：
  名称：

  易于获得呋喃稠合多杂环系统

  摘要：

  以两个不同或不同取代的芳基部分为特征的硝基芪可以从3-硝基苯并[ b ]噻吩与胺的初始开环获得。这种通用结构单元将硝基乙烯基部分的公认双亲电反应性（添加到双键上，然后，例如，硝基的分子内取代）与在电环化过程中利用双键共轭系统的可能性相结合. 在此，亚硝基芪与由双（碳和氧）亲核性提供的不同芳族烯醇反应，产生新颖有趣的萘二氢呋喃。从这些中，作为一种可行的应用，芳构化和电环化反过来导致有价值的缩聚、全芳族O-杂环。

  DOI：

  10.3390/molecules27103147

文献信息

• Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates. A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams
  作者：C. Forzato、P. Nitti、G. Pitacco、E. Valentin、S. Morganti、E. Rizzato、D. Spinelli、C. Dell'Erba、G. Petrillo、C. Tavani

  DOI：10.1016/j.tet.2004.07.084

  日期：2004.11

  Michael addition of lithium enolates of gamma-butyrolactone 1 and alpha-methyl-gamma-butyrolactone 1' to (E)-1-nitropropene 2, (E)-beta-nitrostyrene 3 and (E)-2-vitro-1-phenylpropene 4 is described. Reactions of the lithium enolate of 1' with 2 and 4 occurred with high diasteroselectivity (80 and 92% d.e., respectively). Reactions of the zinc enolate of 1' with two beta-nitroenamines and two methylthiosubstituted 1-amino-2-vitro-1,3-dienes were also examined. Catalytic reduction of the nitroalkylated and nitroalkenylated products allowed the achievement of functionalized gamma-lactams and/or cyclic hydroxamic acids. (C) 2004 Elsevier Ltd. All rights reserved.
• On the reactivity of some 2-methyleneindolines with β-nitroenamines, α-nitroalkenes, and 1,2-diaza-1,3-butadienes
  作者：Orazio A. Attanasi、Gianfranco Favi、Paolino Filippone、Cristina Forzato、Gianluca Giorgi、Stefano Morganti、Patrizia Nitti、Giuliana Pitacco、Egon Rizzato、Domenico Spinelli、Ennio Valentin

  DOI：10.1016/j.tet.2006.04.027

  日期：2006.6

  A study of the behaviour of some electron-rich 2-methyleneindolines (1-3) with different electron-poor reagents (formation of new carbon-carbon and nitrogen-carbon bonds) has furnished interesting results from both synthetic and the mechanistic viewpoints. Enamines 1-3 have been reacted with the beta-nitroenamines 4-7 (reaction CeCl3 center dot 7H(2)O promoted), giving the polymethine dyes 14-23. The same bases 1-3 have been nitroalkylated with the nitroolefins 8-10, furnishing the indolines 24-32, and the diastereoselectivity of the reaction has been thoroughly investigated. The most unexpected results derived from the first example of reaction of Fischer's bases with 1,2-diaza-1,3-butadienes. In fact, with 11-13, the 'unknown' indoline spirodihydropyrroles 33-40 were formed. Their structures were unambiguously assigned, and we determined, as an example, that of 33 by X-ray analysis. (c) 2006 Elsevier Ltd. All rights reserved.
• Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks
  作者：Carlo Dell'Erba、Antonella Gabellini、Marino Novi、Giovanni Petrillo、Cinzia Tavani、Barbara Cosimelli、Domenico Spinelli

  DOI：10.1016/s0040-4020(01)00765-7

  日期：2001.9

  The reaction conditions of the ring-opening processes of 3-nitrothiophene 7a and of 3-nitrobenzo[b]thiophene 7b with pyrrolidine and silver nitrate were optimized as well as those of the subsequent S-methylation of the ensuing silver enethiolates 8a and 8b to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene 9a and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene 9b. Under such conditions 2-X-substituted 4-nitrothiophenes 7c-i consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-X-1,3-butadienes 9c-i. The nitroenamine derivatives 9a-i were then reacted with p-tolylmagnesium bromide to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-X-1,3-butadienes 10a,c-i and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene 10b. Stereochemistry of the interesting building blocks 9a-i and 10a-i was assigned on the grounds of H-1 NMR data and NOE experiments. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Condensed 2-pyrrolidinone-1,2-oxazines from lithium enolate of 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid and β-aryl, β-nitroenamines
  作者：Fulvia Felluga、Valentina Gombac、Giuliana Pitacco、Ennio Valentin、Ennio Zangrando、Stefano Morganti、Egon Rizzato、Domenico Spinelli、Giovanni Petrillo

  DOI：10.1016/j.tet.2006.06.106

  日期：2006.9

  The reaction of the lithium enolate of 1-benzyl-5-oxo-3-pyffolidinecarboxylic acid 3 with a series of beta-aryl, beta-nitroenamines unexpectedly afforded 6-aryl-2-benzyl-4-oxa-l-oxo-3a-methoxycarbonyl-2,5-diazaindenes 9a-d, whose structure was determined by analytical and NMR spectroscopical analysis. The structure of 9b was further confirmed by X-ray analysis. A reasonable mechanism for their formation is given. (c) 2006 Elsevier Ltd. All rights reserved.
• Easy access to 4-nitrothiochroman S,S-dioxides via ring-enlargement from 3-nitrobenzo[b]thiophene
  作者：Lara Bianchi、Carlo Dell'Erba、Massimo Maccagno、Stefano Morganti、Marino Novi、Giovanni Petrillo、Egon Rizzato、Fernando Sancassan、Elda Severi、Domenico Spinelli、Cinzia Tavani

  DOI：10.1016/j.tet.2004.04.039

  日期：2004.5

  easily be oxidized to the relevant sulfones 6 and effectively subjected to cyclization via an intramolecular Michael addition after metallation with lithium bis(trimethylsilyl)amide in THF. After quenching with ammonium chloride the 3-aryl-4-nitrothiochroman S,S-dioxides 2 are obtained as diastereomeric mixtures in good to excellent yields. Both yields and stereochemistry of the ring-closure step appear

  （E）-2-芳基-1- [2-（甲硫基）苯基] -1-硝基乙烯5可以很容易地氧化成相关的砜6并在用双（三甲基甲硅烷基）锂金属化后通过分子内迈克尔加成反应有效地进行环化酰胺在THF中的溶液。用氯化铵淬灭后，以非对映异构体混合物的形式获得3-芳基-4-硝基硫代苯并二氢吡喃S 2，S-二氧化物2，收率良好至优异。闭环步骤的产率和立体化学似乎都受到3-芳基部分的空间效应的影响。由于硫化物5源自3-硝基苯并[ b ]噻吩（1），整个1到2的过程可以被认为是硫杂环的5到6个环的有效扩环。还完成了对分离的非对映异构体2的构象1 H NMR和分子力学研究。