2-[(2Z,4E)-6-chlorohexa-2,4-dienoxy]oxane | 130999-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[(2Z,4E)-6-chlorohexa-2,4-dienoxy]oxane
• CAS: 130999-59-6
• 化学式: C₁₁H₁₇ClO₂
• 分子量: 216.708
• InChiKey: RBSNQJVEJBGSFK-IKENXXAYSA-N

物化性质

• 沸点：
  327.2±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2Z,4E)-6-chlorohexa-2,4-dienoxy]oxane 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-2,9-Bis-methoxycarbonyl-5-methyl-2-[(2E,4Z)-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-dec-5-enedioic acid dimethyl ester
  参考文献：
  名称：

  Transannular Diels-Alder reaction of 14-membered macrocyclic trienes. Part II: Experimental results and synthetic potential

  摘要：

  DOI：

  10.1016/s0040-4039(00)82006-7
• 作为产物：
  描述：

  顺-4-(四氢吡喃-2-氧)-2-丁烯-1-醇 在 2,4,6-三甲基吡啶 、 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 甲基磺酰氯 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成 2-[(2Z,4E)-6-chlorohexa-2,4-dienoxy]oxane
  参考文献：
  名称：

  Ndibwami, Alexis; Lamothe, Serge; Guay, Daniel, Canadian Journal of Chemistry, 1993, vol. 71, # 5, p. 695 - 713

  摘要：

  DOI：

文献信息

• Comparative Effects of Conjugated and Deconjugated Isomeric Enones on the Transannular Diels−Alder Reaction
  作者：Franck Caussanel、Pierre Deslongchamps、Yves L. Dory

  DOI：10.1021/ol035791z

  日期：2003.12.1

  [GRAPHICS]Two isomeric cyclic trienones 2 and 3 (with four methyl esters at positions 3 and 10) underwent transannular Diels-Alder (TADA) reaction at very different temperatures. This drastic difference could be traced to the capacity of the enone dienophile to be conjugated or unconjugated at the transition state. Molecular modeling could confirm this explanation. The calculated enone proved to be very distorted in transition state ts2, and the TADA reaction temperature was accordingly much higher than the one corresponding to ts3 in which the enone was flat.
• Cantin, Michel; Xu, Yao-Chang; Deslongchamps, Pierre, Canadian Journal of Chemistry, 1990, vol. 68, # 12, p. 2144 - 2152
  作者：Cantin, Michel、Xu, Yao-Chang、Deslongchamps, Pierre

  DOI：——

  日期：——
• Transannular Diels–Alder Studies of 14-Membered cis – trans – trans Macrocyclic Trienes Having Allylic Ether or Enone Dienophile
  作者：Rico Lavoie、Stéphane G Ouellet、Carol Dallaire、Yves L Dory、András Toró、Pierre Deslongchamps

  DOI：10.1016/s0040-4020(00)00455-5

  日期：2000.7

  Highly convergent, malonate alkylation based syntheses of the model macrocycles and their title investigations are reported. In the allylic ether dienophile case, a preference for tricycles with equatorial ether position was found at the transition state level. Ab initio calculations also show that the origin of this preference is not only steric but stereoelectronic as well. The enone dienophile case indicates that when the enone system is not totally twisted out of planarity by the macrocyclic environment, the Diels-Alder reaction follows the usual trend in terms of dienophile activation. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Xu, Yao-Chang; Cantin, Michel; Deslongchamps, Pierre, Canadian Journal of Chemistry, 1990, vol. 68, # 12, p. 2137 - 2143
  作者：Xu, Yao-Chang、Cantin, Michel、Deslongchamps, Pierre

  DOI：——

  日期：——
• Transannular Diels-Alder reaction of 14-membered macrocyclic trienes. Part II: Experimental results and synthetic potential
  作者：Serge Lamothe、Alexis Ndibwami、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)82006-7

  日期：1988.1