2,4-hexadienoic acid | 161814-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,4-hexadienoic acid
• 英文别名: sorbic acid；(2E)-2,4-Hexadienoic acid；(2E)-hexa-2,4-dienoic acid
• CAS: 161814-42-2
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: WSWCOQWTEOXDQX-FCEBADDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-hexadienoic acid 在 氯化亚砜 、 1,8-双二甲氨基萘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 hexa-1,3,5-trienal
  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

• Simple Synthetic Transformations of Highly Enantio-Enriched 4-Alkyl-2,5,7-cyclooctatrienols into Functionalized Bicyclo[4.2.0]octa-2,4-dienes and 2,6-Cyclooctadienones
  作者：Mauro Pineschi、Federica Del Moro、Paolo Crotti、Franco Macchia

  DOI：10.1002/ejoc.200400355

  日期：2004.11

  4-Alkyl-2,5,7-cyclooctatrienols with high enantiomeric purities (93−96% ee), obtained by an improved copper-phosphoramidite-catalyzed addition of dialkylzinc reagents to cyclooctatetraene monoepoxide, have been subjected to simple and practical manipulations. Simple esterification reactions are able to deliver new functionalized isomeric 8-alkyl-7-acyloxybicyclo[4.2.0]octa-2,4-dienes through a domino

  具有高对映体纯度（93-96% ee）的 4-烷基-2,5,7-环辛三烯醇，通过改进的铜-亚磷酰胺催化将二烷基锌试剂加成到环辛四烯单环氧化物中获得，已经进行了简单实用的操作。简单的酯化反应能够通过重排反应的多米诺序列以良好的产率提供新的官能化异构 8-烷基-7-酰氧基双环 [4.2.0]octa-2,4-二烯。此外，通过简单的热处理，可以从克级反应中有效地获得具有高光学纯度的新型 4-烷基取代-2,6-环辛二烯酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)