3-甲基-2-哌啶基苯并噻唑烷 | 2899-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-甲基-2-哌啶基苯并噻唑烷
• 英文名称: 3-Methyl-2-piperidino-benzothiazolin
• 英文别名: 3-methyl-2-piperidin-1-yl-2H-1,3-benzothiazole
• CAS: 2899-00-5
• 化学式: C₁₃H₁₈N₂S
• 分子量: 234.365
• InChiKey: GHXNSMIFTWGQLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  31.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲基-2-哌啶基苯并噻唑烷 生成 3-methyl-1'-phenyl-3'-p-tolyl-5'-thioxo-3H-spiro[benzothiazole-2,4'-imidazolidin]-2'-one
  参考文献：
  名称：

  Hoffmann,R.W. et al., Chemische Berichte, 1977, vol. 110, p. 23 - 36

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 3-甲基苯并噻唑鎓硫酸甲酯盐 生成 3-甲基-2-哌啶基苯并噻唑烷
  参考文献：
  名称：

  Metzger,J. et al., Bulletin de la Societe Chimique de France, 1964, p. 2857 - 2867

  摘要：

  DOI：

文献信息

• BORDWELL, F. G.;SATISH, A. V., J. AMER. CHEM. SOC., 113,(1991) N, C. 985-990
  作者：BORDWELL, F. G.、SATISH, A. V.

  DOI：——

  日期：——
• Acidities of C2 hydrogen atoms in thiazolium cations and reactivities of their conjugate bases
  作者：Frederick G. Bordwell、A. V. Satish

  DOI：10.1021/ja00003a036

  日期：1991.1

  The equilibrium acidity for the C2-H bond in the 3,4-dimethylthiazolium cation (TZCH+), a model for thiamin, was estimated to be higher than 16 by direct titrations with indicators in DMSO solution. This result is in agreement with several earlier indirect estimates based on kinetic acidities and Bronsted plots, which place the acidity in the 16-20 pK(HA+) region in aqueous solution, but not with a direct titration in aqueous medium made under stopped-flow conditions, which placed the acidity in the region of pK(HA+) almost-equal-to 13. 3-Methylbenzothiazolium cation (BZCH+), which was found to be considerably more acidic, reacted with Et3N in DMSO to give a dimer BZC=CZB. Evidence is presented to show that this and similar dimerizations occur by addition of the conjugate base of BZCH+ to the H-C=N+ bond to the BZCH+ thiazolium cation, followed by deprotonation. The conjugate base of BZCH+ adds to BZCH+ in preference to reacting with excess of electrophiles such as t-buOH, PhCHO, or PhCH=CH2. Amines, such as piperidine, add rapidly to less acidic thiazolium cations under conditions where little or no deprotonation occurs. These observations exclude a carbene mechanism for dimerization and amine adduct formation.