4-chlorocinnamyl isocyanate | 132606-72-5

• 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-chlorocinnamyl isocyanate
• 英文别名: 1-chloro-4-[(E)-2-isocyanatoethenyl]benzene
• CAS: 132606-72-5
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: LFRSQZAIHWLRQL-AATRIKPKSA-N

物化性质

• 沸点：
  273.0±32.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chlorocinnamyl isocyanate 以68%的产率得到
  参考文献：
  名称：

  ARYA V. P.; DAVID J.; GREWAL R. S., INDIAN J. CHEM. , 1977, B 15, NO 7, 635-640

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-3-(4-氯苯基)丙烯酰氯 在 sodium azide 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 生成 4-chlorocinnamyl isocyanate
  参考文献：
  名称：

  Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production

  摘要：

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.

  DOI：

  10.1021/jm00142a024

文献信息

• Cycloaddition reactions of carbodiimides. The first example of an intramolecular Diels–Alder reaction of CC-conjugated carbodiimides
  作者：Pedro Molina、Mateo Alajarín、Angel Vidal

  DOI：10.1039/c39900001277

  日期：——

  An one-pot preparation of α-carbolines and quinindolines from conjugated carbodiimides based on a tandem Intramolecular Diels–Alder cycloaddition/oxidative aromatization is described.

  描述了一种基于串联的分子内Diels-Alder环加成/氧化芳构化反应的共轭碳二亚胺单罐制备α-咔啉和喹啉的方法。
• Thermal-Induced Dimerization Cyclization of Ethyl N-(Styrylcarbamoyl)acetates: Formation of 4-Hydroxy-2(1<i>H</i>)-pyridone-3- carboxamide Derivatives
  作者：Sheng-Yin Zhao、Bao-Shuo Liu、Jing Huang、Shao-Hua Cheng、Yun-xia Deng、Zhi-Yu Shao

  DOI：10.1080/00397911.2013.878360

  日期：2014.7.18

  Abstract Thermal-induced dimerization cyclization of ethyl N-(styrylcarbamoyl)acetate derivatives has been investigated, leading to 4-hydroxy-2(1H)-pyridone-3-carboxamide derivatives with good yields in diphenyl ether on 200–210 °C. Ethyl N-(styrylcarbamoyl)acetate derivatives readily provided the intermolecular cyclization products 4-hydroxy-2(1H)-pyridone-3-carboxylates on reflux in xylene. In addition

  摘要 已经研究了 N-（苯乙烯基氨基甲酰基）乙酸乙酯衍生物的热诱导二聚环化，导致 4-羟基-2（1H）-吡啶酮-3-甲酰胺衍生物在二苯醚中在 200-210 °C 下具有良好的产率。N-(苯乙烯基氨基甲酰基)乙酸乙酯衍生物在二甲苯中回流时容易提供分子间环化产物4-羟基-2(1H)-吡啶酮-3-羧酸酯。此外，还制备了几种相关的 3-acetyl-4-hydroxy-5-phenylpyridin-2(1H)-ones。它提供了 4-羟基-2(1H)-吡啶酮-3-甲酰胺衍生物的有效制备方法。图形概要
• C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal、Pilar Sanchez-Andrada

  DOI：10.1021/jo00029a026

  日期：1992.1

  Iminophosphoranes 2 derived from o-aminostyrenes react with aryl isocyanates to give the corresponding carbodiimides 13 which by thermal treatment at 160-degrees-C undergo 6-pi-electrocyclization to give quinoline derivatives 14. However, the reaction with styryl isocyanates leads to alpha-carbolines 19 through the intermediate carbodiimides 15 which undergo a tandem intramolecular hetero-Diels-Alder cycloaddition/aromatization process to give 19. Similarly, related alpha-carbolines 20-22 can be obtained from the reaction of iminophosphoranes derived from ortho-substituted anilines containing an unsaturated side chain with styryl isocyanates. Iminophosphorane 6a, derived from o-butadienylaniline, and related 10 and 12 react with aryl isocyanates under the same reaction conditions to give quinindoline derivatives 25-27, respectively. Finally, iminophosphoranes 2 and 6 by reaction with ketenes lead directly to quinolines 32 and benzo[b]carbazoles 33, respectively.