(tert-Butylimino)chloromethyl methyl sulfide | 90496-26-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: (tert-Butylimino)chloromethyl methyl sulfide
• 英文别名: Methyl tert-butylcarbonochloridimidothioate；N-tert-butyl-1-methylsulfanylmethanimidoyl chloride
• CAS: 90496-26-7
• 化学式: C₆H₁₂ClNS
• 分子量: 165.687
• InChiKey: OHYSNSXSRMKWNG-UHFFFAOYSA-N

物化性质

• 沸点：
  200.9±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (tert-Butylimino)chloromethyl methyl sulfide 在 敌草腈 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 5-(tert-Butylimino)-3-(2,6-dimethylphenyl)-2-(methylthio)-4-thiazolidinone
  参考文献：
  名称：

  Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates

  摘要：

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.

  DOI：

  10.1021/jo00074a032
• 作为产物：
  描述：

  氯硫基甲烷 、 异氰酸叔丁酯 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (tert-Butylimino)chloromethyl methyl sulfide
  参考文献：
  名称：

  通过将叔丁基异氰酸酯插入活化的硫化物的CS键中来合成硫代亚氨酸酯。硫代亚氨酸酯的重排由1,3 C烷氧基羰基迁移至N

  摘要：

  叔丁基异氰化物插入α-氰基硫化物的碳-硫键中-得到硫代亚氨酸酯- 。所述thioimidates也可以通过的氯取代得到的叔-butylimino氯硫化物- ，这是一种更常用的方法。这些thioimidates重新排列到E和N-乙烯基氨基甲酸酯的Z异构体-通过烷氧基羰基的1,3-Ç到N迁移。

  DOI：

  10.1016/s0040-4020(01)91248-7

文献信息

• New imidoyl isothiocyanates. Chemical behavior in polar solvents. Reaction with sulfenyl thiocyanates: preparation of 1,2-dihydro-2-thioxo-1,3,5-triazines and 1,3,4,6,6a-triazadithia[6aS(IV)]pentalenes
  作者：Georges Morel、Evelyne Marchand、Catherine Haquin、Andre Foucaud

  DOI：10.1021/jo00371a024

  日期：1986.10
• Three-component cyclocondensations. An efficient synthesis of 4-amino-2-(methylthio)imidazolium salts via the reaction of methyl chlorothioimidates with benzaldimines and isocyanides. Autoxidation of the imidazole derivatives
  作者：Yvelise Malvaut、Evelyne Marchand、Georges Morel

  DOI：10.1021/jo00033a038

  日期：1992.3

  Treatment of imino chlorosulfides 1 with a mixture of benzaldimine and isocyanide provides 4-aminoimidazolium chlorides 5. Presumably this reaction involves the N-imidoylbenzylideniminium chlorides 4 as transient intermediates. 1- and 3-tert-Butyl imidazolium salts 5 undergo fast isobutene elimination giving the corresponding imidazole and imidazoline hydrochlorides 10 and 13. Compounds 13 autoxidize to afford 5-hydroxy derivatives 14 under atmospheric oxygen. The structural assignment of 14 has been confirmed by X-ray diffraction analysis. Under similar conditions, treatment of ketimines 17 with methyl chlorothioimidate 1 and isocyanide gives 2-thioxodiazolidines 19.
• Reactions of protonated 1,3-diaza,-4,4-diphenyl-2-(methylthio)butadienes with isocyanides: preparation of imidazole and triazine derivatives
  作者：Georges Morel、Evelyne Marchand、Andre Foucaud、Loic Toupet

  DOI：10.1021/jo00266a035

  日期：1989.3
• C-(Methoxycarbonyl)ketene N-imidoylimine synthesis and rearrangement into methyl 4,6-diazahepta-2,4,6-trienoates. Cycloaddition reactions with isocyanides: preparation of imidazolines
  作者：Georges Morel、Evelyne Marchand、Andre Foucaud

  DOI：10.1021/jo00206a009

  日期：1985.3
• Synthesis of thioimidates by insertion of TerT-butylisocyanide into the C-S bond of activated sulfides. Rearrangement of thioimidates by 1,3 C to N migration of an alkoxycarbonyl group
  作者：G Morel、E Marchand、K.H Nguyen Thi、A Foucaud

  DOI：10.1016/s0040-4020(01)91248-7

  日期：1984.1

  thioimidates can also be obtained via the chlorine substitution of the tert-butylimino chloro sulfides -, which is a more general method. These thioimidates rearrange to E and Z isomers of N-vinylcarbamates - via a 1,3 C to N migration of the alkoxycarbonyl group.

  叔丁基异氰化物插入α-氰基硫化物的碳-硫键中-得到硫代亚氨酸酯- 。所述thioimidates也可以通过的氯取代得到的叔-butylimino氯硫化物- ，这是一种更常用的方法。这些thioimidates重新排列到E和N-乙烯基氨基甲酸酯的Z异构体-通过烷氧基羰基的1,3-Ç到N迁移。