O-Butyl-(2)-S-(4-brom-phenacyl)-dithiocarbonat | 1861-51-4

• 英文名称: O-Butyl-(2)-S-(4-brom-phenacyl)-dithiocarbonat
• CAS: 1861-51-4
• 化学式: C₁₃H₁₅BrO₂S₂
• 分子量: 347.297
• InChiKey: GAIWEMHAFDEPLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O-Butyl-(2)-S-(4-brom-phenacyl)-dithiocarbonat 在 过氧化双月桂酰 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  An Expedient Route to Dihydrothiazines, a Virtually Unknown Class of Heterocycles

  摘要：

  Upon heating at 180-200 degrees C in diphenyl ether, S-(4-oximinoalkyl)xanthates with a secondary isopropyl or isobutyl group on the oxygen undergo a Chugaev elimination followed by ring closure onto the oxime to give dihydrothiazines, a virtually unknown class of heterocycles.

  DOI：

  10.1021/ol402973q
• 作为产物：
  描述：

  O-仲-丁基二硫代碳酸钾 、 2,4'-二溴苯乙酮 以 丙酮 为溶剂， 以86%的产率得到O-Butyl-(2)-S-(4-brom-phenacyl)-dithiocarbonat
  参考文献：
  名称：

  An Expedient Route to Dihydrothiazines, a Virtually Unknown Class of Heterocycles

  摘要：

  Upon heating at 180-200 degrees C in diphenyl ether, S-(4-oximinoalkyl)xanthates with a secondary isopropyl or isobutyl group on the oxygen undergo a Chugaev elimination followed by ring closure onto the oxime to give dihydrothiazines, a virtually unknown class of heterocycles.

  DOI：

  10.1021/ol402973q

文献信息

• A Synthesis of (1<i>E</i>,3<i>E</i>)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination
  作者：Kelvin Kau Kiat Goh、Sunggak Kim、Samir Z. Zard

  DOI：10.1021/jo402169v

  日期：2013.12.6

  An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.