3-benzylthio-3-methyl-1-butyl p-toluenesulfonate | 74253-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzylthio-3-methyl-1-butyl p-toluenesulfonate
• 英文别名: (3-Benzylsulfanyl-3-methylbutyl) 4-methylbenzenesulfonate
• CAS: 74253-01-3
• 化学式: C₁₉H₂₄O₃S₂
• 分子量: 364.53
• InChiKey: LOZWMEAZZJWZHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzylthio-3-methyl-1-butyl p-toluenesulfonate 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氨 、 sodium 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-(dimethylamino)-N-(4-methyl-4-nitrososulfanylpentyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 哌啶 、 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 11.5h， 生成 3-benzylthio-3-methyl-1-butyl p-toluenesulfonate
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p

文献信息

• Sulfur participation in solvolysis involving four-membered ring intermediates
  作者：Ernest L. Eliel、William H. Pearson、Linda M. Jewell、Anthony G. Abatjoglou、William R. Kenan

  DOI：10.1016/s0040-4039(01)85465-4

  日期：1980.1

  Neighboring group participation via four-membered ring intermediates resulting in complete rearrangement occurs in the methanolysis of R1R2C(SCH2C6H5)CH2CH(R3)OTs when R1=R2=R3=Me and when R1=R2=Me, R3=H. No rearrangement is found for R1=R2=R3=H or R1=R2=H, R3=Me. The case of R1=Me, R2=R3=H is intermediate.

  当R 1 = R 2 = R 3 = Me时，在R 1 R 2 C（SCH 2 C 6 H 5）CH 2 CH（R 3）OTs的甲醇分解中，经由四元环中间体的相邻基团参与导致完全重排。当R 1＝ R 2＝ Me时，R 3＝ H。对于R 1＝ R 2＝ R 3＝ H或R 1＝ R 2＝ H，R 3＝ Me ，没有发现重排。R 1 = Me，R 2的情况= R 3 = H是中间的。
• Neighboring group participation by sulfur involving four-membered-ring intermediates (RS-4)
  作者：Ernest L. Eliel、David E. Knox

  DOI：10.1021/ja00296a019

  日期：1985.5

  On etudie les produits de methanolyse et de trifluoroethanolyse ainsi que les vitesses de methanolyse d'un certain nombre de p-toluenesulfonates d'alkylthio-3 et d'arylthio-3 propyle substitues sur la chaine

  On etudi les produits demethylyse et de trifluoroethanolyse ainsi que les vitesses demethylyse d'un some nombre de p-甲苯磺酸 d'alkylthio-3 et de d'arylthio-3 propyle substitues
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.