3-methyl-2-(2-naphthyl)-1-butene | 75458-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methyl-2-(2-naphthyl)-1-butene
• 英文别名: 2-(3-Methylbut-1-en-2-yl)naphthalene
• CAS: 75458-72-9
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: ZMUHUNSHHQXSOP-UHFFFAOYSA-N

物化性质

• 沸点：
  307.2±9.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  3-methyl-2-(2-naphthyl)-1-butene 在 C₃₇H₃₄ClIrNO₂P 、 sodium t-butanolate 作用下， 以 乙醇 为溶剂， 以98 %的产率得到(S)-2-(3-methylbutan-2-yl)naphthalene
  参考文献：
  名称：

  铱催化 1-芳基-1-烷基乙烯与乙醇的不对称转移氢化

  摘要：

  以手性(PCN)Ir配合物为预催化剂，开发了1-芳基-1-烷基乙烯与乙醇的不对称转移氢化反应，具有对映选择性高、官能团耐受性好、操作简单等特点。该方法进一步应用于无需外部氢供体的烯醇的正式分子内不对称转移氢化，同时产生叔立构中心和远程酮基。克级合成和( R )-黄根醇关键前体的合成凸显了催化系统的实用性。

  DOI：

  10.1021/acs.orglett.3c01880
• 作为产物：
  描述：

  2-甲基-1-萘-2-基丙烷-1-酮 、 甲基三苯基溴化膦 在 苯基锂 作用下， 以 乙醚 为溶剂， 生成 3-methyl-2-(2-naphthyl)-1-butene
  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

• Highly Enantioselective Hydrovinylation of α-Alkyl Vinylarenes. An Approach to the Construction of All-Carbon Quaternary Stereocenters
  作者：Wen-Jian Shi、Qi Zhang、Jian-Hua Xie、Shou-Fei Zhu、Guo-Hua Hou、Qi-Lin Zhou

  DOI：10.1021/ja057654y

  日期：2006.3.1

  The highly enantioselective hydrovinylation of alpha-alkyl vinylarenes was realized by using nickel complexes of chiral spiro phosphoramidite ligands. The method provided a new approach to the construction of chiral all-carbon quaternary centers.

  α-烷基乙烯基芳烃的高度对映选择性氢乙烯基化是通过使用手性螺亚磷酰胺配体的镍配合物实现的。该方法为构建手性全碳四元中心提供了一种新方法。
• Molecular Complexation and Kinetics for Diels−Alder Condensation of Naphthylalkenes with Tetracyanoethylene
  作者：LeRoy H. Klemm、Wayne C. Solomon、Amir P. Tamiz

  DOI：10.1021/jo9804902

  日期：1998.9.1

  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.