3,4-Pentadienoyl chloride | 251911-48-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 3,4-Pentadienoyl chloride
• CAS: 251911-48-5
• 化学式: C₅H₅ClO
• 分子量: 116.547
• InChiKey: BDJIIMSOGNIZJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-Pentadienoyl chloride 在 1,8-双二甲氨基萘 作用下， 生成 Allenylketen
  参考文献：
  名称：

  Heptafulvenone, Vinylketene, Butadienylketene, and Allenylketene − Facile Generation, Observation, and Radical Reaction with TEMPO

  摘要：

  Heptafulvenone (1), vinylketene (11), 1,3-butadienylketene [(E)-15], and allenylketene (21) have been prepared by reaction of the corresponding acyl chlorides with 1,8-bis(dimethylamino)naphthalene as long-lived species in solution at room temperature, and their ketenyl IR bands observed under these conditions for the first time, at 2101, 2118, 2111, 2117 cm(-1), respectively. These unsaturated ketenes react with tetramethylpiperidinyloxyl (TEMPO, TO.) with initial attack at the carbonyl carbon giving delocalized radicals which give from 1 a mixture of the ring contracted o-, m-, and p-formylbenzoates O=CHC6H4CO2T (6) and the bis(cycloheptatrienyl) dimer 7. The products from 11, (E)-15, and 21 are the bis(TEMPO) adducts. (E,Z)-TOCH2CH= CHCO2T (12), (E,E)-TOCH2CH=CHCH=CHCO2T (17), and (E,Z)-CH2=C(OT)CH=CHCO2T (22), respectively.

  DOI：

  10.1002/1099-0690(200109)2001:18<3415::aid-ejoc3415>3.0.co;2-w
• 作为产物：
  描述：

  penta-3,4-dienoic acid 在 氯化亚砜 作用下， 生成 3,4-Pentadienoyl chloride
  参考文献：
  名称：

  Heptafulvenone, Vinylketene, Butadienylketene, and Allenylketene − Facile Generation, Observation, and Radical Reaction with TEMPO

  摘要：

  Heptafulvenone (1), vinylketene (11), 1,3-butadienylketene [(E)-15], and allenylketene (21) have been prepared by reaction of the corresponding acyl chlorides with 1,8-bis(dimethylamino)naphthalene as long-lived species in solution at room temperature, and their ketenyl IR bands observed under these conditions for the first time, at 2101, 2118, 2111, 2117 cm(-1), respectively. These unsaturated ketenes react with tetramethylpiperidinyloxyl (TEMPO, TO.) with initial attack at the carbonyl carbon giving delocalized radicals which give from 1 a mixture of the ring contracted o-, m-, and p-formylbenzoates O=CHC6H4CO2T (6) and the bis(cycloheptatrienyl) dimer 7. The products from 11, (E)-15, and 21 are the bis(TEMPO) adducts. (E,Z)-TOCH2CH= CHCO2T (12), (E,E)-TOCH2CH=CHCH=CHCO2T (17), and (E,Z)-CH2=C(OT)CH=CHCO2T (22), respectively.

  DOI：

  10.1002/1099-0690(200109)2001:18<3415::aid-ejoc3415>3.0.co;2-w

文献信息

• Heptafulvenone, Vinylketene, Butadienylketene, and Allenylketene − Facile Generation, Observation, and Radical Reaction with TEMPO
  作者：Thomas T. Tidwell、Michael H. Fenwick

  DOI：10.1002/1099-0690(200109)2001:18<3415::aid-ejoc3415>3.0.co;2-w

  日期：2001.9

  Heptafulvenone (1), vinylketene (11), 1,3-butadienylketene [(E)-15], and allenylketene (21) have been prepared by reaction of the corresponding acyl chlorides with 1,8-bis(dimethylamino)naphthalene as long-lived species in solution at room temperature, and their ketenyl IR bands observed under these conditions for the first time, at 2101, 2118, 2111, 2117 cm(-1), respectively. These unsaturated ketenes react with tetramethylpiperidinyloxyl (TEMPO, TO.) with initial attack at the carbonyl carbon giving delocalized radicals which give from 1 a mixture of the ring contracted o-, m-, and p-formylbenzoates O=CHC6H4CO2T (6) and the bis(cycloheptatrienyl) dimer 7. The products from 11, (E)-15, and 21 are the bis(TEMPO) adducts. (E,Z)-TOCH2CH= CHCO2T (12), (E,E)-TOCH2CH=CHCH=CHCO2T (17), and (E,Z)-CH2=C(OT)CH=CHCO2T (22), respectively.