2-hydroxyimino-3-oxo-dithiobutyric acid methyl ester | 1609182-76-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: 2-hydroxyimino-3-oxo-dithiobutyric acid methyl ester
• 英文别名: Methyl 2-hydroxyimino-3-oxobutanedithioate
• CAS: 1609182-76-4
• 化学式: C₅H₇NO₂S₂
• 分子量: 177.248
• InChiKey: CMJOMELESASLCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxyimino-3-oxo-dithiobutyric acid methyl ester 、 丁炔二酸二乙酯 以60%的产率得到5-acetyl-2-carboethoxy methylene-6-methylsulfanyl-3-oxo-1,4-thiazine
  参考文献：
  名称：

  Easy access to α-hydroxyimino-β-oxodithioesters and application towards the synthesis of diverse 1,4-thiazine-3-ones via reduction/annulation cascade

  摘要：

  An operationally simple and facile synthesis of alpha-hydroxyimino-beta-oxodithioesters has been achieved by nitrosation of alpha-enolicdithioesters. They were further treated with internal alkynes to afford diverse 1,4-thiazin-3-ones via domino reduction/annulation strategy under mild reaction conditions. Importantly, this is the first straightforward entry to highly functionalized 1,4-thiazin-3-one derivatives from simple starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.097
• 作为产物：
  描述：

  3-Hydroxydithiobuten-(2)-saeuremethylester 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以75%的产率得到2-hydroxyimino-3-oxo-dithiobutyric acid methyl ester
  参考文献：
  名称：

  Easy access to α-hydroxyimino-β-oxodithioesters and application towards the synthesis of diverse 1,4-thiazine-3-ones via reduction/annulation cascade

  摘要：

  An operationally simple and facile synthesis of alpha-hydroxyimino-beta-oxodithioesters has been achieved by nitrosation of alpha-enolicdithioesters. They were further treated with internal alkynes to afford diverse 1,4-thiazin-3-ones via domino reduction/annulation strategy under mild reaction conditions. Importantly, this is the first straightforward entry to highly functionalized 1,4-thiazin-3-one derivatives from simple starting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.097

文献信息

• Access to Fully Substituted Thiazoles and 2,3-Dihydrothiazoles via Copper-Catalyzed [4 + 1] Heterocyclization of α-(<i>N</i>-Hydroxy/aryl)imino-β-oxodithioesters with α-Diazocarbonyls
  作者：Abhijeet Srivastava、Gaurav Shukla、Dhananjay Yadav、Maya Shankar Singh

  DOI：10.1021/acs.joc.7b01601

  日期：2017.10.20

  An efficient chemoselective practical route to fully substituted thiazoles and 2,3-dihydrothiazoles has been devised by [4 + 1] heterocyclization of α-(N-hydroxy/aryl)imino-β-oxodithioesters with in situ generated Cu-carbenoids of diazocarbonyls. The α-(N-hydroxy/aryl)imino-β-oxodithioesters are readily accessible by the reaction of β-oxodithioesters with nitrous acid/nitrosoarenes. The overall transformation

  通过将α-（N-羟基/芳基）亚氨基-β-氧代二硫酯与原位生成的重氮羰基Cu-类胡萝卜素进行[4 +1]杂环化，已设计出一种有效的化学选择性实用途径，可完全取代噻唑和2,3-二氢噻唑。通过β-氧代二硫代酯与亚硝酸/亚硝基芳烃的反应可容易地获得α-（N-羟基/芳基）亚氨基-β-氧代二硫代酯。整个转化过程包括依次进行N–O / C–N键断裂，然后在一个反应​​池中形成级联的C–N / C–S键。这种新策略可以完全控制噻唑环不同位置上各种敏感官能团的引入，从而拓宽了获得此类支架的合成方法的范围。