α-phenylsulfonyl-4-nitrocinnamonitrile

• 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: α-phenylsulfonyl-4-nitrocinnamonitrile
• 英文别名: (E)-3-(4-nitrophenyl)-2-(phenylsulfonyl)acrylonitrile；(E)-2-(benzenesulfonyl)-3-(4-nitrophenyl)prop-2-enenitrile
• 化学式: C₁₅H₁₀N₂O₄S
• 分子量: 314.321
• InChiKey: ASXONLPZYZIBLO-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-nitrobenzylidene)-5-methyl-4,5-dihydro-3H-1λ⁵-pyrazol-3-one 、 α-phenylsulfonyl-4-nitrocinnamonitrile 以 甲苯 为溶剂， 反应 12.0h， 以72%的产率得到(1R,2S,3S)-5-methyl-1,3-bis(4-nitrophenyl)-7-oxo-2-(phenylsulfonyl)hexahydropyrazolo[1,2-a]pyrazole-2-carbonitrile
  参考文献：
  名称：

  Reactions of 3-methyl-2-oxopyrazolidinium ylides with phenylsulfonylacrylonitriles

  摘要：

  A series of methyl oxopyrazolidinium ylides was reacted with (E)-3-(2-hydroxyphenyl)-2-(phenyl-sulfonyl)acrylonitrile and 2-phenylsulfonyl acrylonitrile to give rise to (1R,2S,3S)-5-methyl-7-oxo-1,3-p-substituteddiphenyl-2-(phenylsulfonyl)-hexahydropyrazolo[1,2-a]pyrazole-2-carbonitriles through a sequential reaction accompanying methyl pyrazolone and o-quinone methide releases possibly instead of an anticipated cycloaddition process and 1,3-dipolar cycloaddition route. All the new products were identified by means of spectral/physical characteristics including X-ray diffraction data and HRMS measurements. In addition, a plausible mechanism is proposed for hydroxyphenyl substituted acrylonitrile case. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.022
• 作为产物：
  描述：

  对硝基苯甲醛 、 苯磺酰乙腈 在 potassium fluoride 、 natural phosphate 、 苄基三乙基氯化铵 作用下， 以 乙醇 为溶剂， 反应 0.6h， 以97%的产率得到α-phenylsulfonyl-4-nitrocinnamonitrile
  参考文献：
  名称：

  用于生产精细化学品的固体催化剂：仅使用天然磷酸盐和掺杂的碱催化剂用于合成不饱和芳基砜

  摘要：

  廉价的天然磷酸盐，单独使用或掺有氟化钾，是合成α，β-不饱和芳基砜的一种新型碱性催化剂。还研究了用水和苄基三乙基氯化铵的活化。当使用铵盐时，掺有氟化钾的天然磷酸盐是合成α，β-不饱和芳基砜的极佳固体载体，可在数分钟内获得优异的收率。

  DOI：

  10.1016/j.tet.2003.11.086

文献信息

• Enantioselective cyclopropanation of conjugated cyanosulfones using carbohydrate-based crown ether catalysts
  作者：Tamás Nemcsok、Zsolt Rapi、Péter Bagi、Ying Hou Guan、István Orbán、György Keglevich、Péter Bakó

  DOI：10.1016/j.tet.2020.130965

  日期：2020.2

  lariat ethers have been synthesized. These macrocycles and their derivatives proved to be efficient catalysts in the cyclopropanation of (E)-3-phenyl-2-(phenylsulfonyl)acrylonitrile performed with diethyl bromomalonate under mild phase transfer conditions. Among the catalysts tested, the macrocycle having methyl α-d-galactopyranoside unit generated the highest asymmetric induction (80% ee). In the

  已经合成了一些新的基于d-半乳糖和d-葡萄糖的monoaza-15-crown-5型套索状醚。这些大环及其衍生物被证明是在温和的相转移条件下用溴代丙二酸二乙酯对（E）-3-苯基-2-（苯磺酰基）丙烯腈进行环丙烷化反应的有效催化剂。在所测试的催化剂中，具有甲基α- d-吡喃半乳糖苷单元的大环化合物产生最高的不对称诱导（80％ee）。在芳基取代的苯磺酰基-丙烯腈衍生物的反应中，间位和对位的环丙烷化发生了高ee值（75-84％ee）的替代原料。由具有萘基，吡啶基，呋喃基和噻吩基的类似的α，β-不饱和氰砜合成的环丙烷衍生物的对映选择性高达85％，收率很高。
• Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ³-amino acids
  作者：Lewis S. Aitken、Lisa E. Hammond、Rajkumar Sundaram、Kenneth Shankland、Geoffrey D. Brown、Alexander J. A. Cobb

  DOI：10.1039/c5cc05158d

  日期：——

  A novel hydroquinine derived organocatalyst has been used to make cyclopropanes useful in the construction of δ³-amino acids.

  一种新型的羟基喹啉衍生有机催化剂已被用于制备环丙烷，用于构建δ³-氨基酸。
• Na2CaP2O7, a new catalyst for the synthesis of unsaturated arylsulfones
  作者：Mohamed Zahouily、Mohamed Salah、Jamal Bennazha、Ahmed Rayadh、Saı̈d Sebti

  DOI：10.1016/s0040-4039(03)00630-0

  日期：2003.4

  The synthetic diphosphate Na2CaP2O7 is a new basic catalyst for the synthesis of unsaturated arylsulfones. The condensation was carried out under mild conditions at room temperature in methanol or ethanol. The optimum of the catalyst's activity is reached when water is added, leading to good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Solid catalysts for the production of fine chemicals: the use of natural phosphate alone and doped base catalysts for the synthesis of unsaturated arylsulfones
  作者：Mohamed Zahouily、Mohamed Salah、Bouchaib Bahlaouane、Ahmed Rayadh、Abdelaziz Houmam、Emad A Hamed、Saı̈d Sebti

  DOI：10.1016/j.tet.2003.11.086

  日期：2004.2

  The inexpensive natural phosphate, both alone and doped with potassium fluoride, is a new basic catalyst for the synthesis of α,β-unsaturated arylsulfones. Activation by water and benzyltriethylammonium chloride has also been investigated. When using an ammonium salt, natural phosphate doped with potassium fluoride is an excellent solid support for the synthesis of α,β-unsaturated arylsulfones, leading

  廉价的天然磷酸盐，单独使用或掺有氟化钾，是合成α，β-不饱和芳基砜的一种新型碱性催化剂。还研究了用水和苄基三乙基氯化铵的活化。当使用铵盐时，掺有氟化钾的天然磷酸盐是合成α，β-不饱和芳基砜的极佳固体载体，可在数分钟内获得优异的收率。
• Reactions of 3-methyl-2-oxopyrazolidinium ylides with phenylsulfonylacrylonitriles
  作者：Yaşar Dürüst、Eda Sağırlı、Akın Sağırlı

  DOI：10.1016/j.tet.2015.10.022

  日期：2015.12

  A series of methyl oxopyrazolidinium ylides was reacted with (E)-3-(2-hydroxyphenyl)-2-(phenyl-sulfonyl)acrylonitrile and 2-phenylsulfonyl acrylonitrile to give rise to (1R,2S,3S)-5-methyl-7-oxo-1,3-p-substituteddiphenyl-2-(phenylsulfonyl)-hexahydropyrazolo[1,2-a]pyrazole-2-carbonitriles through a sequential reaction accompanying methyl pyrazolone and o-quinone methide releases possibly instead of an anticipated cycloaddition process and 1,3-dipolar cycloaddition route. All the new products were identified by means of spectral/physical characteristics including X-ray diffraction data and HRMS measurements. In addition, a plausible mechanism is proposed for hydroxyphenyl substituted acrylonitrile case. (C) 2015 Elsevier Ltd. All rights reserved.