1-naphthyl p-tolyl sulphoxide | 10375-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthyl p-tolyl sulphoxide
• 英文别名: 1-(p-tolylsulfinyl)naphthalene；α-Naphthyl-p-tolyl-sulfoxid；1-(4-methylphenyl)sulfinylnaphthalene
• CAS: 10375-69-6
• 化学式: C₁₇H₁₄OS
• 分子量: 266.364
• InChiKey: INOVBEPVVYCPRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-naphthyl p-tolyl sulphoxide 在 碘苯 、 nickel(II) chloride hexahydrate 、 silver(I) acetate 、 aluminium hydride 、 溶剂黄146 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,1,2,2-四氯乙烷 为溶剂， 反应 48.0h， 生成 10-methylbenzo[kl]thioxanthene
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j
• 作为产物：
  描述：

  naphthalen-1-yl(p-tolyl)sulfane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-naphthyl p-tolyl sulphoxide
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j

文献信息

• Use of carbohydrates in the preparation of optically active sulphoxides
  作者：Damon D. Ridley、Mary A. Smal

  DOI：10.1039/c39810000505

  日期：——

  The diastereomeric sulphinate esters formed from arenesulphinyl chlorides and 1,2:5,6-di-O-cyclo-hexylidene-D-glucofuranose afford optically active sulphoxides on treatment with Grignard reagents.

  由芳烃亚磺酰氯和1,2：5,6-二-O-环己叉基-D-葡萄糖呋喃糖形成的非对映异构亚磺酸酯在用格氏试剂处理时提供旋光性亚砜。
• Transition-Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
  作者：Hao Yu、Zhen Li、Carsten Bolm

  DOI：10.1021/acs.orglett.8b03046

  日期：2018.11.16

  A transition-metal-free arylation of sulfenate anions generated from β-sulfinyl esters with diaryliodonium salts was developed. In this process, a new C–S bond is formed under mild reaction conditions providing a wide range of S,S-diaryl and S-alkyl S-aryl sulfoxides.

  从β生成的次磺酸阴离子的过渡金属芳基化自由-与二芳基碘盐亚磺酰酯的开发。在此过程中，在温和的反应条件下形成了一个新的C–S键，提供了广泛的S，S-二芳基和S-烷基S-芳基亚砜。
• Kinetic resolution of sulphoxides by chiral poly(N-alkyliminoalanes)
  作者：Rita Annunziata、Guido Borgogno、Fernando Montanari、Silvio Quici、Salvatore Cucinella

  DOI：10.1039/p19810000113

  日期：——

  Kinetic resolution of racemic sulphoxides by chiral poly[N-(1-phenylethyl)iminoalanes](PIA-PHETs) from (+)- or (–)-1-phenylethylamine is described. For p-tolyl mesityl sulphoxide in the temperature range between –25 and +85 °C, optical yields increase with temperature to an upper limit of between 55 and 70 °C, with enantiomeric enrichments up to ca. 75%. It is shown that, among the three molecular

  描述了由（+）-或（-）-1-苯基乙胺中的手性聚[ N-（1-苯基乙基）亚氨基丙氨酸]（PIA-PHETs）消旋亚砜的动力学拆分。对于p -甲苯基三甲苯基砜在-25和85℃之间的温度范围，光学收率随着温度增加至55和70之间上限℃，用对映体富集高达CA。75％。结果表明，在PIA-PHET的三个分子种类（闭笼四聚体，闭笼六聚体和开笼四聚体）中，只有最后一个具有化学活性并能够进行手性识别。反应遵循二级动力学（在亚砜中一级，在开放式PIA-PHET四聚体中一级）。后者的特定分子结构可能解释了高温下手性的高度识别。
• Colonna,S.; Stirling,C.J.M., Journal of the Chemical Society. Perkin transactions I, 1974, p. 2120 - 2122
  作者：Colonna,S.、Stirling,C.J.M.

  DOI：——

  日期：——
• Thermal racemization of diaryl, alkyl aryl, and dialkyl sulfoxides by pyramidal inversion
  作者：Dennis R. Rayner、Arnold J. Gordon、Kurt Mislow

  DOI：10.1021/ja01020a019

  日期：1968.8