1-(dimethylaminothiocarbonylthio)propan-2-one | 19204-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: 1-(dimethylaminothiocarbonylthio)propan-2-one
• 英文别名: α-(dimethylthiocarbamoylthio)acetone；dimethyl-dithiocarbamic acid acetonyl ester；Dimethyl-dithiocarbamidsaeure-acetonylester；(Dimethyl-thiocarbamoylmercapto)-aceton；acetonyl dimethyldithiocarbamate；N,N-Dimethyl-dithiocarbaminsaeure-<2-oxo-propylester>；Carbamic acid, dimethyldithio-, acetonyl ester；2-oxopropyl N,N-dimethylcarbamodithioate
• CAS: 19204-12-7
• 化学式: C₆H₁₁NOS₂
• mdl: MFCD01738142
• 分子量: 177.291
• InChiKey: OYUFLGHVVZZHLL-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  236.6±42.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(dimethylaminothiocarbonylthio)propan-2-one 在 羟胺 作用下， 生成 dimethyl-dithiocarbamic acid-(2-benzoyloxyimino-propyl ester)
  参考文献：
  名称：

  Nachmias, Annales de Chimie (Cachan, France), 1952, vol. <12> 7, p. 584,599

  摘要：

  DOI：
• 作为产物：
  描述：

  福美双 、 丙酮 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 反应 24.0h， 以84%的产率得到1-(dimethylaminothiocarbonylthio)propan-2-one
  参考文献：
  名称：

  TBD-catalyzed α-sulfenylation of cyclic ketones: desymmetrization of 4-substituted cyclohexanones

  摘要：

  A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the alpha-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.124

文献信息

• THE REACTION OF TETRAMETHYLTHIURAMDISULPHIDE WITH ACETONE: I. REACTION PRODUCTS
  作者：J. R. Robinson、David Craig、Ray B. Fowler

  DOI：10.1139/v56-209

  日期：1956.11.1

  Tetramethylthiuramdisulphide reacts with acetone to form various dithiocarbamate derivatives of acetone, dimethylamine, and carbon disulphide. The reaction has an induction period which is markedly influenced by various additives. The reaction products, their properties and synthesis, are described.

  四甲基硫代二硫代甲酸酯与丙酮反应，形成丙酮、二甲胺和二硫化碳的各种二硫代氨基甲酸酯衍生物。该反应具有明显受各种添加剂影响的诱导期。描述了反应产物、其性质和合成方法。
• Asymmetric Reduction of α-(Dimethylthiocarbamoylthio) Carbonyl Compounds with Bakers’ Yeast
  作者：Sadao Tsuboi、Noriyuki Kohara、Katsumi Doi、Masanori Utaka、Akira Takeda

  DOI：10.1246/bcsj.61.3205

  日期：1988.9

  Treatment of α-(dimethylthiocarbamoylthio) ketones with bakers’ yeast afforded the corresponding chiral alcohols in high yields with high enantiomeric excess (in most cases, more than 96% ee). α-(Dimethylthiocarbamoylthio) aldehydes were reduced to give chiral α-(dimethylthiocarbamoylthio) alcohols in 69–92% yields with 32–63% ee, which were converted to chiral 1,2-epithio derivatives.

  用面包酵母处理 α-（二甲基硫代氨基甲酰硫基）酮以高产率和高对映体过量（在大多数情况下，超过 96% ee）提供相应的手性醇。α-（二甲基硫代氨基甲酰硫基）醛被还原为手性 α-（二甲基硫代氨基甲酰硫基）醇，收率 69-92%，ee 为 32-63%，转化为手性 1,2-epithio 衍生物。
• Dithiocarbamate ester bactericides and fungicides
  申请人：American Cyanamid Company

  公开号：US04011230A1

  公开（公告）日：1977-03-08

  The present invention relates to certain novel dithiocarbamate esters, methods for their synthesis and their use as bactericidal and fungicidal agents.

  本发明涉及某些新型二硫代氨基甲酸酯，其合成方法及其作为杀菌和杀真菌剂的用途。
• 4-Thiazoline-2-thiones. I. The Structure of Intermediate 4-Hydoxythiazolidine-2-thiones
  作者：W. J. Humphlett、R. W. Lamon

  DOI：10.1021/jo01031a008

  日期：1964.8
• Chanon,M.; Metzger,J., Bulletin de la Societe Chimique de France, 1968, p. 2842 - 2846
  作者：Chanon,M.、Metzger,J.

  DOI：——

  日期：——