2-methyl-1-phenylsulfanylnaphthalene | 93322-81-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-1-phenylsulfanylnaphthalene
• 英文别名: 2-methyl-1-phenylsulfonylnaphthalene；(2-Methyl-naphthyl-(1))-phenylsulfid；2-Methyl-1-(phenylsulfanyl)naphthalene
• CAS: 93322-81-7
• 化学式: C₁₇H₁₄S
• 分子量: 250.364
• InChiKey: BULNGAGWWLWVKB-UHFFFAOYSA-N

物化性质

• 沸点：
  387.2±11.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-1-phenylsulfanylnaphthalene 在 双氧水 、 溶剂黄146 作用下， 生成 1-(苯磺酰基)-2-甲基萘
  参考文献：
  名称：

  Butyllithium-Induced Rearrangement of Methylnaphthyl Phenyl Sulfones^1,2

  摘要：

  DOI：

  10.1021/jo01044a029
• 作为产物：
  描述：

  1-溴-2-甲基萘 、 苯硫酚铜(I) 在 吡啶 、 喹啉 作用下， 生成 2-methyl-1-phenylsulfanylnaphthalene
  参考文献：
  名称：

  Butyllithium-Induced Rearrangement of Methylnaphthyl Phenyl Sulfones^1,2

  摘要：

  DOI：

  10.1021/jo01044a029

文献信息

• Carbon–Sulfur Bond Formation Catalyzed by [Pd(IPr*^OMe)(cin)Cl] (cin = cinnamyl)
  作者：Gulluzar Bastug、Steven P. Nolan

  DOI：10.1021/jo401492n

  日期：2013.9.20

  The newly prepared complex [Pd(IPr*OMe)(cin)(Cl)] provides high catalytic activity for carbon–sulfur cross-coupling reactions. Nonactivated and deactivated aryl halides were successfully coupled with a large variety of aryl- and alkylthiols using this well-defined palladium N-heterocyclic carbene (NHC) complex.

  新制备的配合物[Pd（IPr * OMe）（cin）（Cl）]为碳-硫交叉偶联反应提供了高催化活性。使用这种定义明确的钯N-杂环卡宾（NHC）配合物，可以将未活化和失活的芳基卤化物与各种芳基和烷基硫醇成功偶联。
• Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution
  作者：D. Casarini、E. Foresti、F. Gasparrini、L. Lunazzi、D. Misiti、D. Macciantelli、C. Villani

  DOI：10.1021/jo00073a028

  日期：1993.10

  Barriers for the EZ interconversion of atropisomers of 1-naphthyl sulfoxides (ArSOR) having a methyl group at position 2 of the naphthalene moiety were measured by variable-temperature NMR. Their values were found to cover the range 10.6-18.4 kcal mol-1, the extreme values corresponding to derivatives 1 (R = Me) and 4 (R = Bu(t)), respectively. NOE and LIS measurements indicated that the Z atropisomer is more stable than the E but that the absence of the methyl group at position 2 of the naphthalene moiety reverses this trend, rendering E more stable than Z. Solid-state NMR and X-ray diffraction of 4 established that only the more stable atropisomer (Z) is present in the crystalline state. Molecular mechanics calculations suggest that the Z,E interconversion process might occur by a rotation pathway having an opposite direction in the case of the more hindered derivatives 3 and 4 (R = Pr(i) and Bu(t), respectively) with respect to the less hindered 1 and 2 (R = Me and Et, respectively). The enantiomers, which are due to the presence of the asymmetric sulfur atom, were resolved on a chiral stationary phase (DACH-DNB) having an SS configuration. Asymmetric oxidation reactions were employed to assign the absolute R configuration to the more retained enantiomers of alkyl aryl sulfoxides. The opposite trend (S being retained longer) was observed for diaryl sulfoxides such as 5 (R = Ph). In the case of the derivative with the largest interconversion barrier, sulfoxide 4, it was also possible to resolve (at -35-degrees-C) the two enantiomeric forms and their associated atropisomers. The use of on-line CD detection and the knowledge of the NMR assignments allowed us to unambiguously assign the elution order of the four species as ES, ER, ZS, ZR.
• ——
  作者：A. S. Dneprovskii、I. V. Fedosov

  DOI：10.1023/a:1013456112725

  日期：——

  4-Vinylbenzyl phenyl ether, 4-phenylbenzyl phenyl ether, 1- and 2-naphtllylmethyl phenyl ethers react with sodium thiophenolate under photochemical stimulation with replacement of the phenoxy group. The composition of reaction products and relation of reactivity to the structure of substrates is consistent with anion-radical mechanism. The corresponding methoxy and cyano derivatives do not undergo the reaction.