1-(环己基甲基)萘 | 64833-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(环己基甲基)萘
• 英文名称: 1-(cyclohexylmethyl)naphthalene
• CAS: 64833-56-3
• 化学式: C₁₇H₂₀
• 分子量: 224.346
• InChiKey: WNPVZWULJSPNSL-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125.3 °C
• 沸点：
  355.5±9.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  环己氯化镁 在 三乙基硅烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 19.0h， 生成 1-(环己基甲基)萘
  参考文献：
  名称：

  1-Naphthylcarbene: spectroscopy, kinetics, and mechanisms

  摘要：

  DOI：

  10.1021/ja00274a013

文献信息

• Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides
  作者：Dianhu Zhu、Leiyang Lv、Zihang Qiu、Chao-Jun Li

  DOI：10.1021/acs.joc.9b00649

  日期：2019.5.17

  nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

  开发了有效的镍催化的Umpolung羰基化合物与烷基卤化物的交叉偶联。作为经典烷基化技术的补充，该反应利用Umpolung羰基化合物作为对环境无害的烷基亲核试剂，为传统的高反应性烷基有机金属试剂的使用提供了有效和选择性的催化替代方法。
• Kinetic isotope effects as probes of the mechanism of reaction of 1-naphthylcarbene with cyclohexane and toluene
  作者：G. William Griffin、Keith A. Horn

  DOI：10.1021/ja00250a027

  日期：1987.8

  The rates of reaction of 1-naphthylcarbene (1-NC) in hydrocarbon solution have been measured with excimer laser flash photolysis of 1-naphthyldiazomethane. The kinetic data were obtained by monitoring the growth of the 1-naphthylmethyl radical (1-NCH) at 370 nm. The observed kinetic deuterium isotope effect for the reaction of 1-NC with cyclohexane (cyclohexane-d/sub 12/) in 2,2,4-trimethylpentane

  1-萘基卡宾 (1-NC) 在烃溶液中的反应速率已通过 1-萘基重氮甲烷的准分子激光闪光光解进行测量。动力学数据是通过在 370 nm 处监测 1-萘基甲基自由基 (1-NCH) 的生长获得的。观察到的 1-NC 与环己烷 (环己烷-d/sub 12/) 在 2,2,4-三甲基戊烷 (k/sub H//k/sub D/ = 1.32 +/- 0.17) 中的动力学氘同位素效应) 和高 CH 插入与 H 原子提取产物比率与 1-NC 的主要单线态反应性一致。在甲苯中，芳环的添加比氢原子提取更受青睐，测得的逆同位素效应 (k/sub H//k/sub D/ = 0.52 +/- 0.05) 也表明主要是单线态反应性和小单线态-三重态能隙。
• Ionic iron(III) complexes bearing a dialkylbenzimidazolium cation: Efficient catalysts for magnesium-mediated cross-couplings of aryl phosphates with alkyl bromides
  作者：Zhuang Li、Bing Lu、Hongmei Sun、Qi Shen、Yong Zhang

  DOI：10.1002/aoc.3671

  日期：2017.8

  A series of ionic iron(III) complexes of general formula [HLn][FeX4] (HL1 = 1,3‐dibenzylbenzimidazolium cation, X = Cl, 1; HL1, X = Br, 2; HL2 = 1,3‐dibutylbenzimidazolium cation, X = Br, 3; HL3 = 1,3‐bis(diphenylmethyl)benzimidazolium cation, X = Br, 4) were easily prepared in high yields by the direct reaction of FeX3 with 1 equiv. of [HLn]X under mild conditions. All of them were characterized using

  一系列通式为[HL n ] [FeX 4 ]的离子铁（III）配合物（HL 1  = 1,3-二苄基苯并咪唑鎓阳离子，X = Cl，1； HL 1，X = Br，2； HL 2  = 1通过将FeX 3与1当量直接反应，可以轻松地高收率制备 3,3-二丁基苯并咪唑鎓阳离子，X = Br，3 ; HL 3 = 1,3-双（二苯基甲基）苯并咪唑鎓阳离子，X = Br，4）。在温和条件下的[HL n ] X值。所有元素均使用元素分析，拉曼光谱和电喷雾电离质谱法以及X射线晶体学进行了表征1和4。在存在镁屑和LiCl的情况下，这些对空气和水分不敏感的络合物在芳基磷酸酯与伯和仲烷基溴化物的直接交叉偶联中具有较高的催化活性，其中络合物4最有效。
• 铁催化剂在还原偶联反应中的应用和芳环及杂环衍生物的制备方法
  申请人：川北医学院

  公开号：CN111302880B

  公开（公告）日：2022-09-13

  本发明提供了一种铁催化剂在酚类衍生物与烷基卤代物还原偶联反应中的应用，且铁催化剂为溴化亚铁或碘化亚铁。本发明还提供了一种芳环及杂环衍生物的制备方法，采用上述的铁催化剂催化酚类衍生物与烷基卤代物的还原偶联反应，制得芳环及杂环衍生物。本发明首次将铁催化剂应用到酚类衍生物与烷基卤代物还原偶联反应中，铁催化剂成本较低，且无毒性，酚类衍生物的使用同样降低了制备成本；并以酚类衍生物与烷基卤代物为反应物，四甲基乙二胺作配体，甲醇锂作碱，甲基叔丁基醚用作溶剂，制备了芳环及杂环衍生物，制备工艺简单易控制，成本较低，产率较高，有效解决了催化剂及反应原料成本高、毒性大和环境不友好等问题，具有广阔的应用前景。
• Photochemistry of 2,3-di(1'-naphthyl)oxiranes. Spectral and kinetic behavior of carbonyl ylides in condensed media
  作者：K. B. Clark、K. Bhattacharyya、P. K. Das、J. C. Scaiano、A. P. Schaap

  DOI：10.1021/jo00039a036

  日期：1992.6

  The photochemistry of cis- and trans-2,3-di(1'-naphthyl)oxiranes (c- and t-1) has been studied by nanosecond laser flash photolysis in fluid solution. Direct photolysis (lambda(exc) = 248, 266, 308 nm) produces carbonyl ylides which are characterized by broad, structureless absorption bands in the visible region (450-650 nm, lambda(max) approximately 545) and unusually short lifetimes (14-22 ns) in a variety of solvent systems. Triplet energy transfer to the oxiranes results in formation of naphthalene-like triplets (lambda(max) = 410-420 nm, tau(T) < 80 ns) which act as precursors to carbonyl ylides that exhibit spectra (lambda(max) approximately 540-570) similar to those formed via direct excitation but are longer lived (tau = 40-70 ns). In contrast to triplet sensitization, there is no evidence of triplet oxiranes formed via direct excitation. Direct photolysis of the oxiranes appears to result in singlet-mediated photochemistry which initially gives rise to one-bond fragmentation yielding the ultra-short-lived ground-state ylides. Direct photolysis also leads to the formation of 1-naphthaldehyde and 1-naphthylcarbene via either two-bond fragmentation of the singlet excited oxirane or fragmentation of the ground-state carbonyl ylides. A portion of the fragmentation process appears to occur adiabatically as evidenced by the observation of triplet 1-naphthaldehyde in the transient absorption phenomena. In acetonitrile, the transient absorption spectra from direct laser photolysis (308 nm) reveal evidence for photoionization of the oxiranes giving radical cations (lambda(max) approximately 620 nm).