2-(Benzothiazol-2-ylsulfanyl)-4-methyl-1-phenyl-pent-4-en-1-one | 162707-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Benzothiazol-2-ylsulfanyl)-4-methyl-1-phenyl-pent-4-en-1-one
• CAS: 162707-90-6
• 化学式: C₁₉H₁₇NOS₂
• 分子量: 339.482
• InChiKey: OHRYEHVEZUMLKX-UHFFFAOYSA-N

物化性质

• 沸点：
  492.1±55.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(Benzothiazol-2-ylsulfanyl)-4-methyl-1-phenyl-pent-4-en-1-one 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 4-甲基-1-苯基戊-4-烯-1-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：

  2-(1,3-苯并噻唑-2-基硫烷基)-1-苯基乙酮 、 methyl 2-methylprop-2-enyl carbonate 在 palladium diacetate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到2-(Benzothiazol-2-ylsulfanyl)-4-methyl-1-phenyl-pent-4-en-1-one
  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

文献信息

• Aminium Salts Induced Desulphurization of Allyl and Diallyl Thiiranes. Synthesis of Dienes and Trienes
  作者：Vincenzo Caló、Luigi Lopez、Angelo Nacci、Giuseppe Mele

  DOI：10.1016/0040-4020(95)00502-y

  日期：1995.8

  conversion of methylene chloride in solutions of several allyl and diallyl episulphides 1–6 into the corresponding unsaturated derivatives 7–12. The desulphurization process, which occurs through a plausible chain electron-transfer mechanism, rapid and may proceed in a fashion that preserves the stereochemistry of the starting episulphide.

  催化量的铵盐AB会诱导二氯甲烷在几种烯丙基和二烯丙基环氧乙烷1–6的溶液中转化为相应的不饱和衍生物7–12。脱硫过程是通过合理的链电子转移机制而迅速进行的，并且可能以保留起始硫化物的立体化学的方式进行。
• 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。
• 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.