(+/-)-cis-1,2,3,4,4a,5,6,8a-octahydro-naphthalene | 1123-79-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: (+/-)-cis-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
• 英文别名: (+/-)-cis-1,2,3,4,4a,5,6,8a-Octahydro-naphthalin；(+/-)-cis-Δ¹-Octalin；1,2,3,4,4a,5,6,8a-Octahydro-naphthalin；(4As,8aS)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
• CAS: 1123-79-1；2001-49-2；4276-46-4
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: FYHNWJNOEQBNGO-VHSXEESVSA-N

物化性质

• 沸点：
  188.9±7.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 生成 萘烷
  参考文献：
  名称：

  LIN, YI-TSONG;HOUK, K. N., TETRAHEDRON LETT., 1985, 26, N 19, 2269-2272

  摘要：

  DOI：
• 作为产物：
  描述：

  5-己烯-1-醇 在 四(三苯基膦)钯 吡啶 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 gas 为溶剂， 生成 (+/-)-cis-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
  参考文献：
  名称：

  Experimental Determination of the Activation Parameters and Stereoselectivities of the Intramolecular Diels−Alder Reactions of 1,3,8-Nonatriene, 1,3,9-Decatriene, and 1,3,10-Undecatriene and Transition State Modeling with the Monte Carlo-Jumping Between Wells/Molecular Dynamics Method

  摘要：

  Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.

  DOI：

  10.1021/ja9643331

文献信息

• Convenient syntheses of hydroindans and hydronaphthalenes
  作者：Ta-Shue Chou、Hsi-Hwa Tso、Lee-Jean Chang

  DOI：10.1039/c39850000236

  日期：——

  enes, prepared by direct deprotonation and alkylation of 3-sulpholenes, led to cheletropic extrusion of SO2 followed by intramolecular Diels–Alder reaction to yield the corresponding hydroindans and hydronaphthalenes.

  通过直接对3-亚砜进行去质子化和烷基化反应制备的几种新的2-（ω-烯基）-3-亚砜的热解导致SO 2的亲压挤出，然后通过分子内Diels-Alder反应生成相应的氢化茚和氢化萘。
• Synthesis of the Pyrrolo[2,3-i]isoquinoline Substructure of the Manzamine Family of Alkaloids
  作者：David J. Hart、Jeffrey A. McKinney

  DOI：10.1016/s0040-4039(00)99077-4

  日期：1989.1

  synthesis of the tricyclic pyrrolo[2,3-i]isoquinoline substructure of manzamines A, B ,E and F is described. Reductive alkylation of benzoic acid followed by a 3-aza-6-heptenyl radical cyclization gave octahydro-isoquinoline 9. An electrophile initiated cyclization was used to complete construction of the title ring system.

  描述了manzamines A，B，E和F的三环吡咯并[2,3- i ]异喹啉亚结构的首次合成。苯甲酸的还原烷基化，然后进行3-氮杂-6-庚烯基的环化反应，得到八氢异喹啉9。亲电试剂引发的环化反应用于完成标题环系统的构建。
• Singlet and triplet excited-state formation in high-energy electron tracks in liquid cis- and trans-decalin as studied by product formation in radiolysis and photolysis
  作者：A. Hummel、H. C. de Leng、L. H. Luthjens、L. Wojnárovits

  DOI：10.1039/ft9949002459

  日期：——

  The yields of products formed as a result of irradiation of liquid cis- and trans-decalin with γ-rays and 3 MeV electrons as well as with 7.6 eV photons have been determined by means of gas–liquid chromatography (GLC). The major products for both cis- and trans-decalin are hydrogen, unsaturated C10 products and dimers; in the case of cis-decalin, cis–trans isomerization takes place via a chain reaction

  通过气相-液相色谱法（GLC）确定了用γ射线和3 MeV电子以及7.6 eV光子辐照液体顺式和反式十氢萘所形成的产物的产率。顺式和反式十氢萘的主要产物是氢，不饱和C 10产物和二聚体。如果是顺式-萘烷，则顺式-反式异构化通过连锁反应。单重态和三重态激发态是通过直接激发和高能电子轨道中的电荷复合形成的。由单重态引起的产物形成是通过光解确定的。根据对辐射分解产生的单重态的总产率的了解，可以计算出辐射分解过程中单重态激发态对产物形成的贡献，并将剩余的产物分配给三联体。
• Thermal rearrangements of cyclic allenes retro-ene reactions
  作者：John D. Price、Richard P. Johnson

  DOI：10.1016/s0040-4039(00)98820-8

  日期：1985.1

  Flow vacuum thermolysis (500–650°) of 1,2-cyclonona- and 1,2-cyclodecadienes yields, as primary products, terminal enynes and enedienes. Secondary intramolecular Diels-Alder reactions of the enedienes afford cis and trans bicyclics.

  1，2-环壬二烯和1，2-环癸二烯的流式真空热解（500-650°）作为主要产物终端烯和烯二烯。烯二烯的二次分子内Diels-Alder反应产生顺式和反式双环。
• Why a Proximity-Induced Diels–Alder Reaction Is So Fast
  作者：Elizabeth H. Krenske、Emma W. Perry、Steven V. Jerome、Thomas J. Maimone、Phil S. Baran、K. N. Houk

  DOI：10.1021/ol301083q

  日期：2012.6.15

  Unlike normal Diels–Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo[2.2.2]octene employed in the Baran total synthesis of vinigrol undergoes a quantitative Diels–Alder reaction with a tethered alkene at room temperature. Density functional theory calculations reveal that this unprecedented reactivity originates from a combination of preorganization, diene strain, and tether stabilization

  与无环链二烯与烯烃的正常狄尔斯-阿尔德反应不同，在长春醇的巴兰全合成中使用的乙烯基双环[2.2.2]辛烯在室温下与束缚烯烃进行定量狄尔斯-阿尔德反应。密度泛函理论计算表明，这种前所未有的反应性源于预组织、二烯应变和系链稳定的结合。