N-[bis(methylthio)methylene]benzamide | 51592-27-9

• 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-[bis(methylthio)methylene]benzamide
• 英文别名: Dithiokohlensaeure-S,S-dimethylester-(N'-benzoyl-hydrazon)；Dimethyl benzoylcarbonohydrazonodithioate；N-[bis(methylsulfanyl)methylideneamino]benzamide
• CAS: 51592-27-9
• 化学式: C₁₀H₁₂N₂OS₂
• 分子量: 240.35
• InChiKey: PDQIOZVJBLXBIN-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-4,5,6,7-四氢苯并噻酚-3-羧酸乙酯 、 N-[bis(methylthio)methylene]benzamide 在 溶剂黄146 作用下， 反应 8.0h， 以52%的产率得到5,6,7,8-tetrahydro-2-methylthio-4-oxo[1]benzothieno[2,3-d]pyrimidine-3(4H)-benzamide
  参考文献：
  名称：

  Chowdhury; Rahman; Bhuiyan, Pakistan Journal of Scientific and Industrial Research, 2000, vol. 43, # 4, p. 201 - 204

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl N'-benzoylhydrazinocarbodithioate 、 硫酸二甲酯 在 sodium hydroxide 作用下， 生成 N-[bis(methylthio)methylene]benzamide
  参考文献：
  名称：

  Alkylierung der 3-Acyl-thio- und -dithio-carbazinester-Gruppierung CONHNHCSYR

  摘要：

  Abstract3‐Benzoyl‐thiocarbazic acid O‐methyl ester 7a and 3‐benzoyl‐dithiocarbazic acid methyl ester 7b are methylated, in presence of alkali, at the SH group of 1a, the ene‐thiol tautomer of 1, to give the 3‐benzoyl‐isothiocarbazic acid O, S‐dimethyl ester 8a and the 3‐benzoyl‐isodithiocarbazic acid dimethyl ester 8b resp., which clearly differ from the N‐methylated compounds 11a and 12a or 11b and 12b prepared from the two N‐methyl benzohydrazides 9 and 10 resp. (melting points, thin‐layer chromatography and NMR. spectra).The previously reported [1] ring closure of 3‐(ω‐chloroalkanoyl)‐thiocarbazic acid O‐alkyl esters and ‐dithiocarbazic acid alkyl esters can be interpretated as an intramolecular auto‐alkylation of CONHNHCSYR: the 3‐(chloroacetyl)‐compounds 2 are S‐alkylated (enethiol form) to the six‐membered thiadiazinones 4, but the 3‐(3‐chloropropionyl)‐compounds 3 are N‐alkylated to the pyrazolidinones 6, the five‐membered ring being preferred in the latter case to the seven‐membered ring 5 which would be formed by S‐alkylation. Hence the position of alkylating attack depends on the size of the ring to be formed.As a consequence, starting from 3‐(4‐chlorobutyryl) compounds 13, an alternative between the two N‐alkylation products 14 (five‐membered ring) and 15 (six‐membered ring) would be expected. On the contrary however, a combination of 1,3,4‐thiadiazole ring closure and chlorine elimination predominates, giving the 5‐(3‐hydroxypropyl)‐1,3,4‐thiadiazoles 16. This reaction may proceed via the butyrolactone intermediates 18 and could therefore be interpreted as O‐alkylation followed by rearrangement.

  DOI：

  10.1002/hlca.19740570105

文献信息

• Synthesis, structure, and tuberculostatic activity of dimethyl benzoylcarbonohydrazonodithioates
  作者：Katarzyna Gobis、Henryk Foks、Zofia Zwolska、Ewa Augustynowicz-Kopeć、Marek L. Główka、Andrzej Olczak、Michał Sabisz

  DOI：10.1007/s00706-011-0572-9

  日期：2011.11

  ABSTRACT: New dimethyl benzoylcarbonohydrazonodithioates were obtained by CS2 addition to arylcarboxylic acid hydrazides and methylation of the formed adduct. The new derivatives were tested for their activity against Mycobacterium tuberculosis. Some compounds exhibited high activity toward sensitive and resistant strains. GRAPHICAL ABSTRACT:

  摘要：通过将CS2加到芳基羧酸酰肼中并使形成的加合物甲基化，可以得到新的二甲基苯甲酰基碳酰肼基二硫代二甲基甲酸酯。测试了新衍生物对结核分枝杆菌的活性。一些化合物对敏感和抗性菌株表现出高活性。图形概要：