[2]naphthyl-undecyl sulfide | 47231-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2]naphthyl-undecyl sulfide
• 英文别名: 2-Undecylmercapto-naphthalin；[2]Naphthyl-undecyl-sulfid；2-(Undecylsulfanyl)naphthalene；2-undecylsulfanylnaphthalene
• CAS: 47231-80-1
• 化学式: C₂₁H₃₀S
• 分子量: 314.535
• InChiKey: HRZUGKGXYGEJRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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]naphthyl-undecyl sulfide 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以87%的产率得到萘
  参考文献：
  名称：

  Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies

  摘要：

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.

  DOI：

  10.1021/jo00061a011
• 作为产物：
  描述：

  1-溴十一烷 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [2]naphthyl-undecyl sulfide
  参考文献：
  名称：

  Jones; Reid, Journal of the American Chemical Society, 1938, vol. 60, p. 2454

  摘要：

  DOI：

文献信息

• Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies
  作者：Thomas G. Back、Denise L. Baron、Kexin Yang

  DOI：10.1021/jo00061a011

  日期：1993.4

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.
• Jones; Reid, Journal of the American Chemical Society, 1938, vol. 60, p. 2454
  作者：Jones、Reid

  DOI：——

  日期：——