1-Isocyano-2-methyl-1-tosyl-1-propen | 71333-63-6

• 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: 1-Isocyano-2-methyl-1-tosyl-1-propen
• 英文别名: 1-(1-Isocyano-2-methylprop-1-enyl)sulfonyl-4-methylbenzene
• CAS: 71333-63-6
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: ICKVNDPOSADNTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Isocyano-2-methyl-1-tosyl-1-propen 在 苄基三乙基氯化铵 氢氧化钾 、 potassium tert-butylate 作用下， 以 苯 为溶剂， 反应 2.17h， 生成 4-benzoyl-1-methyl-3-<(E)-2'-phenylethenyl>-2-prop-2'-enylpyrrole
  参考文献：
  名称：

  Chemistry of sulfonylmethyl isocyanides. 30. A new synthesis of indoles by electrocyclic ring closure of dialkenylpyrroles. Synthesis of alkenylpyrroles from 1-tosylalkenyl isocyanides and Michael acceptors

  摘要：

  DOI：

  10.1021/jo00372a006
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 丙酮 生成 1-Isocyano-2-methyl-1-tosyl-1-propen
  参考文献：
  名称：

  α，β-不饱和酮的新合成。1-异氰基-1-甲苯基烯烃的烯丙基烷基化

  摘要：

  通过将缩合产物4（衍生自1和甲苯磺酰基甲基异氰化物）烷基化（引入R 3），将酮（1）同化为烯酮2 ，然后进行酸催化水解。

  DOI：

  10.1016/s0040-4039(01)81237-5

文献信息

• A new synthetic approach to the benzazole ring system. Synthesis and electrocyclic ring closure of dialkenyl and alkenyl-aryl substituted pyrroles, imidazoles and oxazoles
  作者：Janusz Moskal、Pens van Stralen、Djurre Postma、Albert M. van Leusen

  DOI：10.1016/s0040-4039(00)84479-2

  日期：1986.1

  An efficient synthesis is described of the substituted azoles referred to in the title, which are precursors of an equally successful new synthetic approach to indoles, benzimidazoles and benzoxazoles.

  描述了标题中所述的取代的吡咯的有效合成，它们是同等成功的吲哚，苯并咪唑和苯并恶唑的新合成方法的前体。
• An Efficient Synthesis of Substituted 3(4)-Nitropyrroles from Nitroalkenes and Tosylmethyl Isocyanides
  作者：Ronald ten Have、Frederik R. Leusink、Albert M. van Leusen

  DOI：10.1055/s-1996-4306

  日期：1996.7

  A series of 3(4)-nitropyrroles with alkenyl substituents in the 2- and 3-positions (or 3-position only) is synthesized efficiently in one operation by a base-induced addition of tosylmethyl isocyanide (TosMIC), or unsaturated homologs of TosMIC, to nitroalkenes.

  通过甲苯磺酰甲基异氰化物 (TosMIC) 或不饱和同系物的碱诱导加成，可在一次操作中有效合成一系列 2-位和 3-位（或仅 3-位）具有烯基取代基的 3(4)-硝基吡咯。 TosMIC，硝基烯烃。
• Isocyanoalkenes, process and useful intermediates for their preparation, pharmaceutical and fungicidal preparations containing those isocyanoalkenes and the use of the fungicidal preparations in agriculture
  申请人：GIST-BROCADES N.V.

  公开号：EP0007672A1

  公开（公告）日：1980-02-06

  Isocysnoalksnes, process and useful intermediates for their preparation, pharmaceutical and fungicidal preparations containing those isocyanoalkenes and the use of the fungicidal preparations in agriculture, the isocyanoalkenes having the general formula: wherein Rx and Ry are the same or different and each is a hydrogen atom or an alkyl, aryl or heterocyclic group and Rx and Ry together with the carbon atom to which they are attached represent a homo- or heterogeneous cydoal- kylidene, adamantylidene or cholestamtlidene group, Rw is an alkylidene group or Rw together with Rx and the carbon atom to which they are attached represent a homo- or heterogeneous cycloalkenyl group and Rz is an aryl group.

  异氰基烯烃、制备它们的工艺和有用中间体、含有这些异氰基烯烃的药物和杀菌制剂以及这些杀菌制剂在农业中的用途，这些异氰基烯烃具有通式： 其中 Rx 和 Ry 相同或不同，且各自为氢原子或烷基、芳基或杂环基团，Rx 和 Ry 与它们所连接的碳原子一起代表同族或异族的亚烷基、亚金刚烷基或亚胆烷基，Rw 为亚烷基或 Rw 与 Rx 和它们所连接的碳原子一起代表同族或异族的环烯基，Rz 为芳基。
• van Leusen,A.M. et al., Recueil des Travaux Chimiques des Pays-Bas, 1979, vol. 98, p. 258 - 262
  作者：van Leusen,A.M. et al.

  DOI：——

  日期：——
• Chemoselective synthesis of 3H-pyrrolo[2,3-c]quinolin-4(5H)-one derivatives from 3-phenacylideneoxindoles and substituted tosylmethyl isocyanide (TosMIC)
  作者：Rong Wang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2013.10.084

  日期：2013.12

  A simple and convenient synthetic approach to access of 3H-pyrrolo[2,3-c]quinolin-4(5H)-one derivatives by the reaction of (Z)-3-(2-oxo-2-ethylidene)indolin-2-one derivatives 1 with functionalized TosMICs under basic conditions has been reported. The desired products were obtained in good to excellent yields (82-94%). The easy accessibility of the starting materials, simple and mild reaction conditions, short reaction time, and good to excellent chemical yields make this methodology highly efficient. (C) 2013 Elsevier Ltd. All rights reserved.