isobutyl α-naphthyl sulfide | 25752-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: isobutyl α-naphthyl sulfide
• 英文别名: tert-butyl(naphthalen-1-yl)sulfane；tert-Butyl-1-naphthylsulfid；(Tert-butylthio)naphthalene；1-tert-butylsulfanylnaphthalene
• CAS: 25752-97-0
• 化学式: C₁₄H₁₆S
• 分子量: 216.347
• InChiKey: KDEVZAOYVIVZQK-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±11.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  isobutyl α-naphthyl sulfide 在 双氧水 、 溶剂黄146 作用下， 生成 tert-Butyl-(1-naphthyl)-sulfon
  参考文献：
  名称：

  Karpenko,R.G. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1945 - 1949

  摘要：

  DOI：
• 作为产物：
  描述：

  1-奈硫酚 、 异丁烯 生成 isobutyl α-naphthyl sulfide
  参考文献：
  名称：

  Karpenko,R.G. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1945 - 1949

  摘要：

  DOI：

文献信息

• Mild Ti-mediated transformation of t-butyl thio-ethers into thio-acetates
  作者：Thomas C. Pijper、Jort Robertus、Wesley R. Browne、Ben L. Feringa

  DOI：10.1039/c4ob02120g

  日期：——

  Rapid conversion of thio-ethers to thio-acetates using TiCl₄that tolerates a wide variety of functionalities, in good to excellent yields.

  硫醚快速转化为硫代醋酸酯，使用TiCl₄催化剂，能容忍多种官能团，收率良好至优异。
• Node, Manabu; Nishide, Kiyoharu; Ohta, Keiichiro, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 2, p. 545 - 551
  作者：Node, Manabu、Nishide, Kiyoharu、Ohta, Keiichiro、Fuji, Kaoru、Fujita, Eiichi、et al.

  DOI：——

  日期：——
• 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.
• Photostimulated reactions of alkanethiolate ions with haloarenes. Electron transfer vs. fragmentation of the radical anion intermediate
  作者：Roberto A. Rossi、Sara M. Palacios

  DOI：10.1021/jo00339a008

  日期：1981.12
• NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS
  申请人：Bristol-Myers Squibb Company

  公开号：US20190322694A1

  公开（公告）日：2019-10-24

  The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.