S-ethyl 2-bromopropanethioate | 209597-98-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-ethyl 2-bromopropanethioate
• CAS: 209597-98-8
• 化学式: C₅H₉BrOS
• 分子量: 197.096
• InChiKey: WWKLDHMLHHWLKP-UHFFFAOYSA-N

物化性质

• 沸点：
  195.8±23.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-ethyl 2-bromopropanethioate 在 氘代甲醇 、 三乙胺 作用下， 以 氘代甲苯 为溶剂， 生成
  参考文献：
  名称：

  Dynamic Enzymatic Resolution of Thioesters

  摘要：

  A detailed investigation of several issues related to the enzymatic resolution of thioesters under conditions of continuous racemization of substrate was conducted. The kinetic acidity of the alpha-protons of a series of alpha-substituted propionate thioesters was studied. It was found that the rate of alpha-proton exchange could be enhanced as much as 20-fold by variation of the thiol moiety, increasing the range of compounds to which enzymatic dynamic resolution may be applied. The relative rates of hydrolysis of ethyl butyrate and ethyl thiobutyrate by several enzymes commonly used in enzymatic resolution were determined. All of the enzymes studied exhibited similar rates of thioester and oxoester hydrolysis except for the esterase from pig liver, which showed very low activity in thioester hydrolysis. Dynamic resolution of the propargyl and trifluoroethyl thioesters of alpha-phenylpropionate was conducted using subtilisin Carlsberg as a catalyst. These examples demonstrated that enzymatic dynamic resolution can be applied even when the rate of alpha-proton exchange and the enantioselectivity of the enzyme are fairly low. A dynamic enzymatic transesterification procedure was demonstrated in the resolution of the trifluoroethyl thioester of alpha-(2,4-dichlorophenoxy)propionate, and product was obtained in 93% ee. This work helps expand and define the scope of enzymatic dynamic resolution of thioesters.

  DOI：

  10.1021/ja980445b
• 作为产物：
  描述：

  2-溴丙酰溴 、 乙硫醇 以 乙醚 为溶剂， 以9.85 g的产率得到S-ethyl 2-bromopropanethioate
  参考文献：
  名称：

  [3+2] 可见光催化芳基环丙基酮环加成反应

  摘要：

  我们报告了一种新的芳基环丙基酮与烯烃的 [3+2] 反应生成高度取代的环戊烷环系统的新方法。该过程中的关键引发步骤是将酮单电子还原为相应的自由基阴离子，这是使用包含 Ru(bpy)(3)(2+)、La(OTf)(3)、和 TMEDA。

  DOI：

  10.1021/ja107849y

文献信息

• Diastereoselective Aldol and Reformatsky Reactions of<b><i>α</i></b>-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride
  作者：Akifumi Kagayama、Koji Igarashi、Isamu Shiina、Teruaki Mukaiyama

  DOI：10.1246/bcsj.73.2579

  日期：2000.11

  Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.

  通过在低温下在二氯甲烷-新戊腈中使用氯化钛 (II) 和碘化铜或碘化钠的组合，成功地进行了 α-溴酮与几种醛的高度非对映选择性羟醛反应。类似地，α-溴硫酯与脂肪醛的 Reformatsky 反应在温和条件下以良好的产率得到 β-羟基硫酯。
• Metal-Free Transfer Hydroiodination of C–C Multiple Bonds
  作者：Weiqiang Chen、Johannes C. L. Walker、Martin Oestreich

  DOI：10.1021/jacs.8b12318

  日期：2019.1.16

  The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Brønsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove

  描述了基于环己-1,4-二烯的气态碘化氢替代品的设计和克级合成。通过用中等强度的布朗斯台德酸引发，碘化氢从替代物转移到 CC 多重键上，例如炔烃和丙二烯，而没有游离碘化氢的参与。代用品碎片化为甲苯和乙烯，易挥发废物。这种氢碘化反应避免了对碘化氢或氢碘酸的不稳定处理。通过这种方式，可以以立体控制的方式访问范围广泛的以前未知或难以制备的乙烯基碘。
• Reductive Mannich-type reaction using the composite reagents of phosphine and Lewis acid
  作者：Satoshi Kikuchi、Takayuki Kobayashi、Yukihiko Hashimoto

  DOI：10.1016/j.tetlet.2006.01.106

  日期：2006.3

  We found that the combination of Ph3P and TiCl4 was the excellent promoter for reductive Mannich-type reaction of S-2,4,6-triisopropylphenyl 2-bromopropanethioate with several imines and that the corresponding products were obtained in good yields with high anti-selectivity.

  我们发现，Ph 3 P和TiCl 4的组合是S -2,4,6-三异丙基苯基2-溴丙烷硫酸酯与几种亚胺的还原曼尼希型反应的极好促进剂，并以高收率和高收率获得了相应的产物。反选择性。
• Diastereoselective Aldol Reaction of<i>α</i>-Bromo Ketones with Aliphatic Aldehydes by Using Titanium(II) Chloride and Copper
  作者：Teruaki Mukaiyama、Akifumi Kagayama、Koji Igarashi、Isamu Shiina

  DOI：10.1246/cl.1999.1157

  日期：1999.11

  Highly diastereoselective aldol reaction of α-bromo ketones with aliphatic aldehydes was successfully carried out by using titanium(II) chloride and copper in dichloromethane at low temperature. Similarly, Reformatsky-type reaction of α-bromo thioester with aliphatic aldehydes was promoted under mild conditions to afford β-hydroxy thioesters in good to moderate yields.

  通过在二氯甲烷中使用氯化钛（II）和铜，在低温下成功地进行了α-溴酮与脂肪醛的高度非对映选择性羟醛反应。类似地，α-溴硫酯与脂肪醛的 Reformatsky 型反应在温和条件下得到促进，以良好到中等的产率得到 β-羟基硫酯。
• 吡啶氧基硫酯衍生物及其制备方法、除草组合 物和应用
  申请人：青岛清原化合物有限公司

  公开号：CN109400526B

  公开（公告）日：2020-10-16

  本发明属于农药技术领域，具体涉及一种吡啶氧基硫酯衍生物及其制备方法、除草组合物和应用。所述吡啶氧基硫酯衍生物如式Ⅰ所示，其中，A、B分别独立地代表卤素，含有或不含有卤素的烷基或环烷基；C代表氢、卤素、烷基、卤代烷基；Q代表卤素，氰基，氰基烷基，羟基烷基，氨基，硝基，甲酰基，不含或含有卤素的烷基等；M代表不含或含有卤素的烷基、烯基等；X代表硝基或NR1R2。所述化合物的除草活性优异，且具有更高的作物安全性，尤其是对于水稻等关键农作物建立了良好的选择性。