3-(1,3-Benzothiazol-2-ylsulfanyl)-5-methylhex-5-en-2-one | 162707-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(1,3-Benzothiazol-2-ylsulfanyl)-5-methylhex-5-en-2-one
• CAS: 162707-89-3
• 化学式: C₁₄H₁₅NOS₂
• 分子量: 277.411
• InChiKey: LUJIWYYCOLKUJT-UHFFFAOYSA-N

物化性质

• 沸点：
  397.7±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-Benzothiazol-2-ylsulfanyl)-5-methylhex-5-en-2-one 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 5-甲基-5-己烯-2-酮
  参考文献：
  名称：

  Palladium-catalysed synthesis of α-diallylated ketosulphides of benzothiazole and their transformation into diallyl thiiranes and trienes

  摘要：

  alpha-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording alpha,alpha-diallylated ketosulphides 2 in high yields. Reduction of 2 with sodium borohydride in isopropanol gives episulphides which in turn can be transformed almost quantitatively into trienes.

  DOI：

  10.1016/0040-4039(94)02204-o
• 作为产物：
  描述：

  1-(2-苯并噻唑基硫代)-2-丙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium diacetate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到3-(1,3-Benzothiazol-2-ylsulfanyl)-5-methylhex-5-en-2-one
  参考文献：
  名称：

  苯并噻唑的烯丙基化酮硫化物作为烯丙基酮，烯丙基硫烷和二烯的立体选择性合成的中间体

  摘要：

  在乙酸钯存在下于二氯甲烷中，在温和条件下，苯并噻唑1的α-酮硫化物与碳酸烯丙酯反应，以高收率得到α-和α，α-二烯丙基化的酮硫化物2。用氢化三丁基锡对2a-d进行还原性脱硫得到二烯丙基化的酮3a-d，而在异丙醇中用硼氢化钠还原单烯丙基化2e-k则得到烯丙基环氧乙烷4e-k，主要是（Z）-异构体，可以将其立体选择性地转化为二烯。

  DOI：

  10.1016/0040-4020(95)01030-0

文献信息

• Stereoselective synthesis of 1,4-dienes by chelation-controlled reduction of benzothiazole β-oxosulfides
  作者：Vincenzo Caló、Angelo Nacci

  DOI：10.1016/s0040-4039(98)00622-4

  日期：1998.5

  Allylated beta-oxosulfides of benzothiazole can replace beta-oxophosphane oxides to provide a stereospecific alkene synthesis. These sulfides, by reduction with sodium borohydride afford predominantly syn beta-hydroxy sulfides. DIBAL reduction in the presence of magnesium bromide improves the syn stereomer formation. Base treatment of these beta-hydroxy sulfides affords (Z)-allyl thiiranes which are converted into (E, Z)-dienes. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Palladium-catalysed synthesis of α-diallylated ketosulphides of benzothiazole and their transformation into diallyl thiiranes and trienes
  作者：Vincenzo Caló、Vito Fiandanese、Angelo Nacci、Antonio Scilimati

  DOI：10.1016/0040-4039(94)02204-o

  日期：1995.1

  alpha-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording alpha,alpha-diallylated ketosulphides 2 in high yields. Reduction of 2 with sodium borohydride in isopropanol gives episulphides which in turn can be transformed almost quantitatively into trienes.
• Allylated ketosulphides of benzothiazole as intermediates for stereoselective synthesis of allyl ketones, allyl thiiranes and dienes
  作者：Vincenzo Caló、Vito Fiandanese、Angelo Nacci、Angela Volpe

  DOI：10.1016/0040-4020(95)01030-0

  日期：1996.2

  dichloromethane under mild conditions affording α- and α,α-diallylated ketosulphides 2 in high yields. Reductive desulphurization of 2a–d with tributyltin hydride gives diallylated ketones 3a–d, whereas reduction of mono-allylated 2e–k with sodium borohydride in isopropanol affords allyl episulphides 4e–k prevalently as (Z)-isomers which can be transformed stereoselectively into dienes.

  在乙酸钯存在下于二氯甲烷中，在温和条件下，苯并噻唑1的α-酮硫化物与碳酸烯丙酯反应，以高收率得到α-和α，α-二烯丙基化的酮硫化物2。用氢化三丁基锡对2a-d进行还原性脱硫得到二烯丙基化的酮3a-d，而在异丙醇中用硼氢化钠还原单烯丙基化2e-k则得到烯丙基环氧乙烷4e-k，主要是（Z）-异构体，可以将其立体选择性地转化为二烯。