cis,trans-cyclonona-1,3-diene | 3776-88-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: cis,trans-cyclonona-1,3-diene
• 英文别名: cis,trans-1,3-cyclononadiene；cis,trans-1,3-Cyclononadien；Cyclonona-1,2-dien；(1E,3Z)-cyclonona-1,3-diene
• CAS: 3776-88-3
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: HVSYSQGJZITGQV-HSFFGMMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  cis,trans-cyclonona-1,3-diene 在 palladium on activated charcoal 氢气 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (1R,7R)-4-Phenyl-2,4,6-triaza-tricyclo[5.5.2.02,6]tetradecane-3,5-dione
  参考文献：
  名称：

  Synthesis, structure, and reactivity of the (i,o)-diazabicyclo[n.2.2]alkene skeleton. Extremely facile cleavage of a carbon-nitrogen bond

  摘要：

  DOI：

  10.1021/ja00399a096
• 作为产物：
  描述：

  环庚烯 在 lead(IV) acetate 、 氧气 、 苯乙酮 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 17.0h， 生成 cis,trans-cyclonona-1,3-diene
  参考文献：
  名称：

  Cyclobutene photochemistry. 4. The photochemistry of cis- and trans-bicyclo[5.2.0]non-8-ene

  摘要：

  Direct photolysis of cis- and trans-bicyclo[5.2.0]non-8-ene in hydrocarbon solution with monochromatic far-UV (185-214 nm) light sources affords cis,cis- and cis,trans-1,3-cyclononadiene via formal electrocyclic ring opening, cycloheptene (and acetylene) via formal (sigma-2s + sigma-2s) cycloreversion, and minor amounts of molecular rearrangement products. Product quantum yields have been determined for the 185-nm photolyses. The two isomers lead to similar distributions of the isomeric 1,3-cyclononadienes, with similar quantum yields at 185 nm; the diene mixtures are in both cases weighted in favor of the less thermodynamically stable cis,trans isomer. The product distributions vary only slightly with excitation wavelength over the 185-214-nm range. Quantum yields for direct photoisomerization of cis,cis- and cis,trans-1,3-cyclononadiene have also been determined. Two mechanisms are considered to explain the nonstereospecificity associated with the ring-opening process: a nonconcerted pathway involving initial cyclobutene bond homolysis and subsequent relaxation of common biradical intermediates, and a pericyclic pathway involving adiabatic, disrotatory ring opening to yield dienes in the first excited singlet state. While the results do not allow a definitive distinction between the two mechanisms, the nonconcerted pathway is suggested to be the more reasonable on the basis of the photobehavior of other cyclobutene derivatives that have been studied. The quantum yield of cycloreversion product is ca. 4 times higher from the cis isomer compared to that from the trans isomer, due to the stereochemical requirements of the process.

  DOI：

  10.1021/jo00004a043

文献信息

• The 2π + 2π cycloaddition of an allyl cation to (1Z,3E)-cycloalkadienes. Evidence for a stepwise process in the lonic Diels-Alder reaction.
  作者：Paul G. Gassman、Subhash P. Chavan、Lawrence B. Fertel

  DOI：10.1016/s0040-4039(00)97098-9

  日期：1990.1

  Treatment of (1Z,3E)-cycloalkadienes with 2-vinyl-1,3-dioxolane under acidic conditions produced 1:1 cycloadducts in which an intermediate allyl cation added to the dienes to give trans-fused cyclobutanes as the major products.

  在酸性条件下用2-乙烯基-1,3-二氧戊环处理（1 Z，3 E）-环链二烯可产生1：1的环加合物，其中将中间烯丙基阳离子添加到二烯中，得到反式稠合的环丁烷为主要产物。