(4-methoxyphenyl)(2,3,4,5-tetrapropyl-cyclopenta-2,4-dienylidene)amine | 731842-74-3

• 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: (4-methoxyphenyl)(2,3,4,5-tetrapropyl-cyclopenta-2,4-dienylidene)amine
• 英文别名: N-(4-methoxyphenyl)-2,3,4,5-tetrapropylcyclopenta-2,4-dien-1-imine
• CAS: 731842-74-3
• 化学式: C₂₄H₃₅NO
• 分子量: 353.548
• InChiKey: FZHPYHGHESCGAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基苯基 异硫氰酸酯 、 (5Z,7Z)-6,7-dibutyl-5,8-diiodododeca-5,7-diene 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以74%的产率得到(4-methoxyphenyl)(2,3,4,5-tetrapropyl-cyclopenta-2,4-dienylidene)amine
  参考文献：
  名称：

  Reactions of 1,4-dilithiobutadienes with isothiocyanates: preparation of iminocyclopentadiene derivatives via cleavage of the CS double bond of a RNCS molecule

  摘要：

  Reaction patterns of 1,4-dilithio-butadiene derivatives with isothiocyanates RN=C=S and isocyanates RN=C=O were investigated and synthetically useful preparative methods were developed. Isothiocyanates reacted with 1,4-dilithio-butadienes to afford iminocyclopentadiene derivatives in excellent isolated yields and high selectivity. When aromatic isothiocyanates were used, cleavage of the C=S double bond of a RN C=S molecule took place via a successive inter-intramolecular carbophilic addition. A number of products were obtained from the reaction of isocyanates with 1,4-dilithio-butadienes, probably due to the high reactivity of isocyanates towards 1,4-dilithio-butadienes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.045

文献信息

• Lewis acid-controlled reactions of zirconacyclopentadienes with isocyanates and isothiocyanates. One-pot three- or four-component synthesis of multiply substituted iminocyclopentadienes and butadiene-tethered 1,6-bisamides and electrophilic cyclization
  作者：Qiaoshu Hu、Jiang Lu、Congyang Wang、Chao Wang、Zhenfeng Xi

  DOI：10.1016/j.tet.2007.02.015

  日期：2007.7

  products in high isolated yields from the reactions of zirconacyclopentadienes with isocyanates, depending on the substituents of isocyanates. The reaction path and products could be controlled by Lewis acids. As a demonstration of the usefulness of thus obtained unsaturated bisamides, electrophilic cyclization using acids, NBS, and I2 was carried out. Electrophilic cyclization of multisubstituted conjugated

  取决于路易斯酸，异氰酸酯和异硫氰酸酯的性质，在路易斯酸存在下，多取代的氧化锆环戊二烯（包括双环氧化锆环戊二烯和氧化锆茚）与异氰酸酯和异硫氰酸酯反应，生成亚氨基环戊二烯和共轭1,6-双酰胺。当用异氰酸酯处理氧化锆环戊二烯时，只有在BF 3存在下才能以高分离产率获得亚氨基环戊二烯。相反，BF 3不能介导氧化锆环戊二烯与异硫氰酸酯的反应。对于氧化锆环戊二烯与异硫氰酸酯，EtAlCl 2的反应被发现有效地产生亚氨基环戊二烯作为产物。然而，有趣的是，对于氧化锆环戊二烯与异氰酸酯的反应，发现EtAlCl 2的作用与BF 3完全不同。取代异亚氨基环戊二烯，根据异氰酸酯的取代基，从氧化锆环戊二烯与异氰酸酯的反应以高分离的产率获得了共轭的1，6-双酰胺和共轭的单酰胺。反应路径和产物可以通过路易斯酸来控制。为了证明由此获得的不饱和双酰胺的有用性，使用酸，NBS和I 2进行亲电环化进行了。多取代的共轭1，6-双
• Reactions of 1,4-dilithiobutadienes with isothiocyanates: preparation of iminocyclopentadiene derivatives via cleavage of the CS double bond of a RNCS molecule
  作者：Congyang Wang、Qiuling Song、Zhenfeng Xi

  DOI：10.1016/j.tet.2004.04.045

  日期：2004.6

  Reaction patterns of 1,4-dilithio-butadiene derivatives with isothiocyanates RN=C=S and isocyanates RN=C=O were investigated and synthetically useful preparative methods were developed. Isothiocyanates reacted with 1,4-dilithio-butadienes to afford iminocyclopentadiene derivatives in excellent isolated yields and high selectivity. When aromatic isothiocyanates were used, cleavage of the C=S double bond of a RN C=S molecule took place via a successive inter-intramolecular carbophilic addition. A number of products were obtained from the reaction of isocyanates with 1,4-dilithio-butadienes, probably due to the high reactivity of isocyanates towards 1,4-dilithio-butadienes. (C) 2004 Elsevier Ltd. All rights reserved.