4-chloro-benzaldehyde S-methylisothiosemicarbazone | 59394-85-3

• 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: 4-chloro-benzaldehyde S-methylisothiosemicarbazone
• 英文别名: BTB05196；Isothiosemicarbazon；methyl N'-[(4-chlorophenyl)methylideneamino]carbamimidothioate
• CAS: 59394-85-3
• 化学式: C₉H₁₀ClN₃S
• 分子量: 227.718
• InChiKey: KHROHJUJMJZLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-benzaldehyde S-methylisothiosemicarbazone 以 二苯醚 、 苯 为溶剂， 反应 3.17h， 生成 1-(N-4-chlorophenylmethylideneamino)-1,6-dihydro-2-methylthio-6-oxopyrimidine
  参考文献：
  名称：

  从 Meldrum 酸衍生物合成 1-(N-Alkylidene or Benzylideneamino)-1,6-dihydro-2-methylthio-6-oxo-pyrimidine

  摘要：

  摘要 5-Ethoxymethylene-1,3-dioxane-4,6-dione 与isothiosemicarbazone 反应得到5-isothiosemicarbazone 亚甲基1,3-dioxane-4,6-dione (3)。3 的热解提供了一种新的 1-(N-亚烷基或亚苄基氨基)-1,6-二氢-2-甲硫基-6-嘧啶的合成方法，收率很高。

  DOI：

  10.1081/scc-120016351
• 作为产物：
  描述：

  4-氯苯甲醛 、 S-甲基异硫氨基脲盐酸盐 在 乙醇 、 sodium acetate 作用下， 生成 4-chloro-benzaldehyde S-methylisothiosemicarbazone
  参考文献：
  名称：

  Fenech; Monforte, Annali di Chimica, 1958, vol. 48, p. 1093,1099, 1102

  摘要：

  DOI：

文献信息

• Substituted aminobenzylideneamino guanidine compounds
  申请人：American Cyanamid Company

  公开号：US03941825A1

  公开（公告）日：1976-03-02

  The preparation of 1-amino-3-(4- and 3,4-substituted benzylideneamino)guanidine and the acid addition salts thereof, and their use as intermediates in the preparation of 1,3-bis(4- and 3,4-substituted benzylideneamino)guanidines and their acid addition salts. The final compounds prepared from the present intermediates have antiprotozoal activity particularly against coccidiosis and malaria.

  制备1-氨基-3-(4-和3,4-取代苯基亚胺)胍和其酸加盐，以及它们作为1,3-双(4-和3,4-取代苯基亚胺)胍和其酸加盐制备中间体的用途。从目前的中间体制备的最终化合物具有抗原虫活性，特别针对球虫病和疟疾。
• Cyclization of Isothiosemicarbazones. IV. Synthesis of the [1,2,4]Triazolo[1,5-<i>c</i>]pyrimidine Ring System
  作者：Chiji Yamazaki

  DOI：10.1246/bcsj.54.1767

  日期：1981.6

  Condensation of isothiosemicarbazones with ethoxymethylenemalononitrile gave 2,3-dihydro[1,2,4] triazolo[1,5-c]pyrimidines in moderate to high yields. The 2,3-dihydro compounds were readily oxidized in dimethyl sulfoxide to give the corresponding [1,2,4]triazolo[1,5-c]pyrimidines.

  异缩氨基硫脲与乙氧基亚甲基丙二腈的缩合以中等至高产率得到2,3-二氢[1,2,4]三唑并[1,5-c]嘧啶。2,3-二氢化合物在二甲亚砜中很容易氧化得到相应的[1,2,4]三唑并[1,5-c]嘧啶。
• A novel route to 1-benzyl-1,2,4-triazole derivatives through disproportionation of isothiosemicarbazones
  作者：Chiji Yamazaki、Mariko Ohno

  DOI：10.1002/jhet.5570340305

  日期：1997.5

  Aromatic isothiosemicarbazones 1–4 underwent disproportionation at elevated temperature in the presence of a thiol or a thiol-releasing substance to give 1-arylmethylene-3-alkylthio-5-aryl-1H-1,2,4-triazole derivatives 6–9 in moderate yields. An isothiosemicarbazone of aliphatic aldehyde with no α-hydrogen did not give rise to the corresponding disproportionation under the similar conditions. Cross reaction

  在高温下，在有硫醇或释放硫醇的物质下，芳族异硫代半碳杂唑烷1-4歧化，得到1-芳基亚甲基-3-烷基硫基-5-芳基-1 H -1,2,4-三唑衍生物6-9产量中等。在类似条件下，没有α-氢的脂族醛的异亚氨基脲也不会引起相应的歧化。在两个不同的异硫代咪唑酮之间发生了交叉反应，但只能以较低的收率分离出交叉化合物。任何惰性溶剂都可以显着抑制歧化反应，即使仅将其稀释即可。提出了一个初步的反应机理，其中可能涉及潜在的氮烯-ulf离子对作为关键步骤。
• Cocco; Congiu; Maccioni, Il Farmaco, 1989, vol. 44, # 10, p. 974 - 985
  作者：Cocco、Congiu、Maccioni、Plumitallo、Schivo、De Logu

  DOI：——

  日期：——
• Synthesis of Nitrogen-Containing Heterocycles 11. 1,2,4-Triazole Formation through Disproportionation of Polyazapolyenes
  作者：Yoshiko Miyamoto

  DOI：10.3987/com-07-11268

  日期：——

  Aromatic diaminomethylenehydrazones 1-4 were reacted with bis(methylthio)methylenemalononitrile (BMM) to give 5-aryl-1-benzyl-3dimethylamino-1H-1,2,4-triazoles(5-8) via disproportionation in ftised condition in moderate to high yields (44-78 %). Little or no effect was observed on disproportionation products in connection with substituents on the benzene ring. When used an equimolar amount of two different diaminomethylenehydrazones 3 and 4, four types of 5-aryl-1-benzyl-3-dimethylamino-1H-1,2,4-triazoles were obtained. In the reaction using two (different) benzaldehyde S-methylisothiosemicarbazones 22 and 23, four types of 5-aryl-1-benzyl-3methylthio-1H-1,2,4-triazoles were formed in 14-26 % yield. The structural assignment of products and reaction mechanism are discussed.