N.N-Dimethyl-2-hydroxy-2.2-diphenylthioacetamid | 52417-36-4

• 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: N.N-Dimethyl-2-hydroxy-2.2-diphenylthioacetamid
• 英文别名: 2-hydroxy-N,N-dimethyl-2,2-diphenylethanethioamide
• CAS: 52417-36-4
• 化学式: C₁₆H₁₇NOS
• 分子量: 271.383
• InChiKey: ZTNBRMXQVQEAAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N.N-Dimethyl-2-hydroxy-2.2-diphenylthioacetamid 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2-dimethylamino-3-phenylbenzothiophene
  参考文献：
  名称：

  Ablenas, F. J.; George, B. E.; Maleki, M., Canadian Journal of Chemistry, 1987, vol. 65, p. 1800 - 1803

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯甲酮 、 2-Hydroxy-2,N,N-trimethylthiopropionamid 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 N.N-Dimethyl-2-hydroxy-2.2-diphenylthioacetamid
  参考文献：
  名称：

  亲核试剂Aminoalkylierung麻省理工学院Thiopivalamiden †

  摘要：

  硫代戊酰胺的亲核氨基烷基化1

  DOI：

  10.1002/hlca.19800630111

文献信息

• Seebach,D. et al., Chemische Berichte, 1976, vol. 109, p. 1309 - 1323
  作者：Seebach,D. et al.

  DOI：——

  日期：——
• Reaction of Benzylic α-Hydroxythioamides with Thionyl Chloride
  作者：Xavier Creary、Jennifer Tricker

  DOI：10.1021/jo971590v

  日期：1998.7.1

  9-Hydroxy-9-(N,N-dimethylthiocarbamyl)fluorene,4, reacts very rapidly with 1 equiv of thionyl chloride to give the corresponding alpha-chlorothioamide derivative, 2. However reaction of 4 with 2 equiv of thionyl chloride gives the desulfurized product 9-chloro-9-(N,N-dimethylcarbamyl)fluorene 6. This unusual desulfurization reaction, which is neither completely general nor completely understood at the present time, occurs less readily than initial formation of the alpha-chlorothioamide. The a-chlorothioamide 2 is highly reactive in hydroxylic solvents. The substantially less reactive alpha-chloroamide 6 undergoes reaction in hydroxylic solvents via the intermediacy of the 9-(N,N-dimethylcarbamyl)-9-fluorenyl cation, 15, at rates comparable to those of the or-H analogue, 9-chlorofluorene, 14. Computational studies indicate that the cl-carbonyl cation 15 prefers a conformation in which the carbonyl group is rotated 90 degrees with respect to the fluorenyl system. The relatively rapid rate of solvolysis of 6 is attributed to relief of ground-state strain as the cation 15 forms, as well as delocalization involving the fluorene system. Carbonyl conjugation as a cation-stabilizing feature does not appear to operate in the alpha-carbonyl cation 15.
• Kalinowski,H.-O. et al., Chemische Berichte, 1977, vol. 110, p. 3733 - 3744
  作者：Kalinowski,H.-O. et al.

  DOI：——

  日期：——
• LUBOSCH W.; SEEBACH D., HELV. CHIM. ACTA, 1980, 63, NO 1, 102-116
  作者：LUBOSCH W.、 SEEBACH D.

  DOI：——

  日期：——
• SEEBACH D.; LUBOSCH W.; ENDERS D., CHEM. BER. <CHBE-AM>, 1976, 109, NO 4, 1309-1323
  作者：SEEBACH D.、 LUBOSCH W.、 ENDERS D.

  DOI：——

  日期：——