N-(p-chlorophenyl)-N'-[4-methyl-2-(phenylethynyl)phenyl]carbodiimide | 1019842-19-3

• 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: N-(p-chlorophenyl)-N'-[4-methyl-2-(phenylethynyl)phenyl]carbodiimide
• CAS: 1019842-19-3
• 化学式: C₂₂H₁₅ClN₂
• 分子量: 342.827
• InChiKey: FGSZZHZPWLBSIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(p-chlorophenyl)-N'-[4-methyl-2-(phenylethynyl)phenyl]carbodiimide 在 碘 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 ethyl N-(4-chlorophenyl)-3-iodo-5-methyl-2-phenyl-1Hindole-1-carbimidate
  参考文献：
  名称：

  连续的Aza-Wittig /碘诱导的环化反应有效合成3-碘吲哚N-羧酰亚胺和N-羧酰亚胺

  摘要：

  3-碘代吲哚N-碳亚氨基酰亚胺和N-碳亚氨基磺酸盐4是通过连续的氮杂-Wittig /碘诱导的环化反应选择性地制备的，从容易获得的2-炔基苯基亚氨基正膦，异氰酸酯，各种亲核试剂和碘开始。

  DOI：

  10.1002/cjoc.201200281
• 作为产物：
  描述：

  4-methyl-2-(phenylethynyl)-(N-triphenylphosphoranylidene)phenylamine 、 对氯苯异氰酸酯 以 二氯甲烷 为溶剂， 生成 N-(p-chlorophenyl)-N'-[4-methyl-2-(phenylethynyl)phenyl]carbodiimide
  参考文献：
  名称：

  连续的Aza-Wittig /碘诱导的环化反应有效合成3-碘吲哚N-羧酰亚胺和N-羧酰亚胺

  摘要：

  3-碘代吲哚N-碳亚氨基酰亚胺和N-碳亚氨基磺酸盐4是通过连续的氮杂-Wittig /碘诱导的环化反应选择性地制备的，从容易获得的2-炔基苯基亚氨基正膦，异氰酸酯，各种亲核试剂和碘开始。

  DOI：

  10.1002/cjoc.201200281

文献信息

• Efficient Regioselective Synthesis of Indole <i>N</i>-Carboximidamides and <i>N</i>-Carboximidoates by a Sequential Aza-Wittig/Ag(I)-Catalyzed Cyclization
  作者：Nian-Yu Huang、Ming-Guo Liu、Ming-Wu Ding

  DOI：10.1021/jo901362c

  日期：2009.9.4

  An efficient Ag(I)-catalyzed regioselective cyclization of (2-alkynylphenyl)guanidine or (2-alkynylphenyl)isourea to indole N-carboximidamides or N-carboximidoates has been developed. The approach has the advantages of high regioselectivity, mild reaction conditions, easily accessible starting materials, and good yields.

  已经开发了有效的Ag（I）催化的（2-炔基苯基）胍或（2-炔基苯基）异脲的吲哚区域化成吲哚N-羧酰亚胺或N-羧酰亚胺基。该方法具有区域选择性高，反应条件温和，起始原料容易获得和产率高的优点。
• Thermal C²−C⁶ Cyclization of Enyne−Carbodiimides:  Experimental Evidence Contradicts a Diradical and Suggests a Carbene Intermediate
  作者：Michael Schmittel、Jens-Peter Steffen、David Rodríguez、Bernward Engelen、Elmar Neumann、Mehmet Emin Cinar

  DOI：10.1021/jo701966h

  日期：2008.4.1

  Mechanistic details of the thermal C(2)-C(6) cyclization of enyne-carbodiimides are investigated. A variety of product and kinetic studies on solvent and substituent effects open the way for a deeper mechanistic understanding. Nonlinear Hammett correlations suggest that a change of mechanism takes place: the thermal C(2)-C(6) cyclization of enyne-carbodiimides with electron-withdrawing substituents may be best described as a coarctate cyclization to a carbene and with electron-donating substituents as a polar cyclization to a carbene with strong zwitterionic character. Theoretical investigations had originally suggested a diradical intermediate. DFT computations and NBO analysis for the parent diazafulvenediyl are in agreement with a carbene intermediate. While any intermolecular trapping of the intermediate failed, the formation of the C-H insertion product 19 strongly supports the carbene hypothesis.
• Efficient Regioselective Synthesis of 3-Iodoindole N-Carboximidamides and N-Carboximidoates by a Sequential Aza-Wittig/Iodine Induced Cyclization
  作者：Yibo Nie、Zhuan Duan、Mingwu Ding

  DOI：10.1002/cjoc.201200281

  日期：2012.8

  3‐Iodoindole N‐carboximidamides and N‐carboximidoates 4 were prepared regioselectively via a sequential aza‐Wittig/iodine induced cyclization, starting from easily accessible 2‐alkynylphenyl iminophosphorane, isocyanates, various nucleophiles and iodine.

  3-碘代吲哚N-碳亚氨基酰亚胺和N-碳亚氨基磺酸盐4是通过连续的氮杂-Wittig /碘诱导的环化反应选择性地制备的，从容易获得的2-炔基苯基亚氨基正膦，异氰酸酯，各种亲核试剂和碘开始。