1-Propyl-1-(naphthyl-(2))-aethen | 75412-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Propyl-1-(naphthyl-(2))-aethen
• 英文别名: 2-Pent-1-en-2-ylnaphthalene
• CAS: 75412-19-0
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: JLTBMDIHPINBEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-Propyl-1-(naphthyl-(2))-aethen 、 四氰基乙烯 以 1,2-二氯乙烷 为溶剂， 生成 1-Propyl-3,3,4,4-tetracyan-2,3,4,4a-tetrahydro-phenanthren
  参考文献：
  名称：

  Molecular Complexation and Kinetics for Diels−Alder Condensation of Naphthylalkenes with Tetracyanoethylene

  摘要：

  The charge-transfer spectra of 1:1 molecular complexes of seven 1-alkyl-1-(2-naphthyl)ethenes (where R = alkyl group: H, Me, Et, n-Pr, i-Pr, t-Bu, Neopent) and 1-vinylnaphthalene with TCNE were determined in ClCH2CH2Cl as solvent at 27.1 degrees C. Equilibrium constants, K, for these complexes vary with R, as based on two opposing factors, viz. (a) the polar substituent factor sigma* and (b) the angle-of-twist theta between the planes of the naphthyl and vinyl groups. For R = Neopent (sigma* dominant) K is 50 times as large as for R = t-Bu (theta dominant). Except for R = t-Bu, kinetics of reaction conform with the equation D + TCNE reversible arrow (K) D.TCNE reversible arrow (k(1)/k(-1)) P, where D is the donor alkene, P is the Diels-Alder 1,4-cycloaddition product, and k(1) and k(-1) are first-order reaction rate constants. Values of k(1) vary from 0.71 min(-1) (R = H) to 55.5 min(-1) (R = Neopent) and the corresponding relative second-order rate constants k(2) (or k(1)K) from 1 to 4000. The rate constant k(-1) was measured only for 1b (R = Me, 0.0017 min(-1)) in the solvent mixture p-xylene/ClCH2CH2Cl. Formation of 1b.TCNE complex gives Delta H = 10.0 kcal/mol and Delta S = 38.4 eu, and conversion to P shows an Arrhenius activation energy of E-a = 7.24 kcal/mol. It is proposed that the preferred conformation of a naphthylalkene for complexation has the R and vinyl groups projecting outward from opposite sides of the plane of the naphthalene ring. The TCNE molecule then aligns parallel to the naphthalene ring on the vinyl side where (except for R = t-Bu) it can slide into the geometry of the transition state to form P.

  DOI：

  10.1021/jo9804902
• 作为产物：
  描述：

  1-(2-萘基)-1-丁酮 、 甲基三苯基溴化膦 在 苯基锂 作用下， 以 乙醚 为溶剂， 生成 1-Propyl-1-(naphthyl-(2))-aethen
  参考文献：
  名称：

  Coplanarity Effects on the Spectral, Gas Chromatographic, Polarographic, and Diels-Alder Characteristics of 1-Alkyl-1-(2-naphthyl)ethenes¹

  摘要：

  DOI：

  10.1021/jo01055a017

文献信息

• CN114920652
  申请人：——

  公开号：——

  公开（公告）日：——