N.N-Dimethyl-2-hydroxy-2-phenylthioacetamid | 52417-38-6

• 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-phenylthioacetamid
• 英文别名: 2-hydroxy-N,N-dimethyl-2-phenylethanethioamide
• CAS: 52417-38-6
• 化学式: C₁₀H₁₃NOS
• 分子量: 195.285
• InChiKey: BDPQSYOSFNUMQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-phenylthioacetamid 在 甲烷磺酸 作用下， 以 氯苯 为溶剂， 反应 2.0h， 以31%的产率得到2-dimethylaminobenzothiophene
  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：

  苯甲醛 以65%的产率得到
  参考文献：
  名称：

  SEEBACH D.; LUBOSCH W.; ENDERS D., CHEM. BER. , 1976, 109, NO 4, 1309-1323

  摘要：

  DOI：

文献信息

• Naphthalene-catalysed lithiation of carbamoyl and thiocarbamoyl chlorides under Barbier-type reaction conditions
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/0040-4020(96)00827-7

  日期：1996.10

  The reaction of different carbamoyl or thiocarbamoyl chlorides 1 with carbonyl compounds or imines 2 in the presence of an excess of lithium powder and a catalytic amount of naphthalene (3 mol %) in THF at −78°C leads, after hydrolysis with water, to the expected α-hydroxy or α-amino amides 3, respectively. In the case of allylic or benzylic derivatives 1a,c, when longer reaction times are used, the

  不同的氨基甲酰基或硫代氨基甲酰氯的反应1与羰基化合物或亚胺2在THF过量锂粉末和萘的催化量（3摩尔％）的在-78℃下引线的存在下，用水水解后，以预期的α-羟基或α-氨基酰胺3。在烯丙基或苄基衍生物1a，c的情况下，当使用更长的反应时间时，获得了由脱酰作用或脱​​苄基作用产生的相应产物4。使用DMF或异氰酸苯酯作为亲电试剂可得到取代的乙酰胺5。最后，当预先进行水解时，将过量的烷基氯加入到反应混合物中，形成1，2-二醇6，这是由于将原位生成的烷基锂最后两次加成至最初形成的α-羟基酰胺而产生的。
• Seebach,D. et al., Chemische Berichte, 1976, vol. 109, p. 1309 - 1323
  作者：Seebach,D. et al.

  DOI：——

  日期：——
• Carbamoyl and thiocarbamoyl lithium: A new route by naphthalene-catalysed chlorine-lithium exchange
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(00)61613-1

  日期：1993.10

  The reaction of N,N-diisopropylcarbamoyl or N,N-dimethylthiocarbamoyl chloride (1a or 1b) with an excess of lithium powder and a catalytic amount of naphthalene (3 mol %) in the presence of a carbonyl compound 2 at temperatures ranging between -78 and 20-degrees-C, under Barbier-type conditions leads, after hydrolysis with water, to the corresponding alpha-hydroxy amides or thioamides 3, respectively.
• 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.
• ABLENAS, F. J.;GEORGE, B. E.;MALEKI, M.;JAIN, R.;HOPKINSON, A. C.;LEE-RUF+, CAN. J. CHEM., 65,(1987) N 8, 1800-1803
  作者：ABLENAS, F. J.、GEORGE, B. E.、MALEKI, M.、JAIN, R.、HOPKINSON, A. C.、LEE-RUF+

  DOI：——

  日期：——