1,2,3,4,4-pentachloro-1-(2-hydroxyethylthio)-1,3-butadiene | 14204-54-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,2,3,4,4-pentachloro-1-(2-hydroxyethylthio)-1,3-butadiene
• 英文别名: 2-(1,2,3,4,4-pentachloro-buta-1,3-dienylsulfanyl)-ethanol；2-(1,2,3,4,4-Pentachlorobuta-1,3-dienylsulfanyl)ethanol；2-(1,2,3,4,4-pentachlorobuta-1,3-dienylsulfanyl)ethanol
• CAS: 14204-54-7
• 化学式: C₆H₅Cl₅OS
• 分子量: 302.436
• InChiKey: DWFIVUUIHPZPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4,4-pentachloro-1-(2-hydroxyethylthio)-1,3-butadiene 在 硫酸 、 间氯过氧苯甲酸 、 potassium bromide 作用下， 以 氯仿 为溶剂， 反应 25.5h， 生成 (Z)-1-(2-Bromo-ethanesulfinyl)-1,2,3,4,4-pentachloro-buta-1,3-diene
  参考文献：
  名称：

  N,S-, S-, S,S-, <S═O-, and < SO₂-Substituted Dienes from Halo-1,3-Butadienes

  摘要：

  Mono(thio) substituted dienes 1 gave 3a-g, 5, and 7 with piperazine derivatives in dichloromethane. Hexachlorobutadiene 14 in a water-ethanol mixture in the presence of sodium hydroxide reacted with thiol 15 to give the mono(thio) substituted thioether 16 and di(thio) substituted thioether 17. 18 was obtained from the reaction of 16 with m-CPBA in chloroform. 9 was obtained from the reaction of l,2,3,4,4-pentachloro-(1-2-hydroxyethylthio)-1,3- butadiene 8 with 47% HI, and 11 was synthesized from the reaction of 8 with concentrated H2SO4 and KBr. Compounds 9 and 11 gave in the reaction with m-CPBA in chloroform 10, 12, and 13, respectively.

  DOI：

  10.1080/10426500500272194
• 作为产物：
  描述：

  六氯-1,3-丁二烯 、 2-巯基乙醇 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以76%的产率得到1,2,3,4,4-pentachloro-1-(2-hydroxyethylthio)-1,3-butadiene
  参考文献：
  名称：

  N,S-Substituted Dienes from Mono(arylthio)substituted- and S-, S,S-Substituted Dienes

  摘要：

  Mono(thio)substituted dienes 1a-1b gave compounds 3a-c and 5d-g with piperazine and piperidine derivatives in dichloromethane. Compounds 8, 9, and 10 were obtained from the reactions of perchlorobutadiene (6) with 1,4-butanedithiol (7) in ethanol in the presence of sodium hydroxide. Compounds 12a-b, 13a-b were obtained from the reactions of perchlorobutadiene (6) with allylmercaptan (CH2=CH-CH2-SH) and mercaptoethanol (HO-CH2-CH2-SH).

  DOI：

  10.1080/10426500214874

文献信息

• New Heterocyclic Compounds From Butadienyl Sulfanes and Thiols
  作者：Zeliha Gökmen

  DOI：10.14233/ajchem.2014.15720

  日期：——

  2-Chloroethyl-pentachlorobutadienyl-sulphide reacts with some heterocyclic thiols (7-mercapto-4-methylcoumarin, 2-mercaptobenzimidazole derivatives etc.) in water-ethanol mixture in the presence of sodium hydroxide to give the new heterocyclic thioethers. New 2-(4-(2-chloro-ethylthio)-1,2,3,4-tetrachlorobuta-1,3-dienylthio)ethanol compound was obtained from the reaction of 1,4-bis(2-hydroxyethylthio)-1,2,3,4-tetrachloro-1,3-butadiene with SOCl2 in pyridine. The structures of the new compounds were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, MS and fluorescence spectrophotometry.

  在氢氧化钠存在下，2-氯乙基五氯丁二烯硫醚与一些杂环硫醇（7-巯基-4-甲基香豆素、2-巯基苯并咪唑衍生物等）在水-乙醇混合物中发生反应，生成新的杂环硫醚。在吡啶中，1,4-双（2-羟乙基硫代）-1,2,3,4-四氯-1,3-丁二烯与 SOCl2 反应，得到了新的 2-（4-（2-氯-乙硫基）-1,2,3,4-四氯-1,3-丁二硫基）乙醇化合物。新化合物的结构通过元素分析、傅立叶变换红外光谱、1H NMR、13C NMR、质谱和荧光分光光度法进行了表征。
• New Perchlorobutadienyl Sulfanes
  作者：Zeliha Gökmen、Cemil İbiş

  DOI：10.1080/10426500802073175

  日期：2008.12.23

  Hexachlorobutadiene 1 reacts with 3-mercapto-1-hexanol in water-ethanol mixture in the presence of sodium hydroxide to give the new monosubstituted thioether 3-(perchlorobuta-1,3-dienyl-thio)-hexan-1-ol 3a and the disubstituted thioether 3,3' -(perchlorobuta-1,3-diene-1,4-diyl) bis(sulfane-diyl)-dihexan-1-ol 4a. 1-Chlorohexan-3-yl-pentachlorobutadienyl-sulfide 5a, 2-chloroethyl-penta-chlorobutadienyl-sulfide 5b, 2-chloropropyl-pentachlorobutadienyl-sulfide 5c and 1,2,3,4-tetra-chlorobuta-1,4-bis(2-chloroethylsulfanyl)-buta-1,3-diene 6b were obtained from the reaction of 3a-c and 4b with SOCl2 in pyridine. The derivatives 8b-k and 9a were synthesized from the reaction of componds 5b and 5c in water-ethanol mixture in the presence of sodium hydroxide with the corresponding thiol, respectively.
• The Sulphides, Sulfoxides, and Sulfones of New Dienyl Groups
  作者：Cemil İbiş、Zeliha Gökmen

  DOI：10.1080/713744558

  日期：2003.10.1

  Mono(thio)substituted dienes la-c gave compounds 3a-i with piperazine 2 in dichloromethane. Compounds 5a-c were synthesized from the reaction of mono(thio)substituted la-c with 4-piperidinol 4. Compounds 7a-b were obtained from the reaction of mono(thio)substituted dienes la-b with 2-aminoethylmorpholino 6. N,N-Bis(mono(thio)substituted)-2-nitro-1,3-butadienyl 9a-b were synthesized from the reactions of mono(thio)substituted dienes la-b with 2,5-dimethyl-piperazine 8. Compound 10a was obtained from the reaction of perchlorobutadiene with 2-napthylthiol in ethanol in the presence of sodium hydroxide. Compounds 11a-b were obtained from the reactions of mono(thio)substituted dienes 10a-b with m-chloroperbenzoic acid in CHCl3. Di(thio)substituted diene 12b gave compound mono(sulfnyl)dienes 13b with m-chloroperbenzoic acid in CHCl3, Compound 15 was synthesized from the reaction of tris(thio)substituted nitrodiene 14 with m-chloroperbenzoic acid in CHCl3.
• Maahs,G.; Hegenberg,P., Angewandte Chemie, 1966, vol. 78, p. 939
  作者：Maahs,G.、Hegenberg,P.

  DOI：——

  日期：——
• N,S-, S-, S,S-, &lt;S═O-, and &lt; SO₂-Substituted Dienes from Halo-1,3-Butadienes
  作者：Cemil İbiş、Zeliha Gökmen

  DOI：10.1080/10426500500272194

  日期：2006.4.1

  Mono(thio) substituted dienes 1 gave 3a-g, 5, and 7 with piperazine derivatives in dichloromethane. Hexachlorobutadiene 14 in a water-ethanol mixture in the presence of sodium hydroxide reacted with thiol 15 to give the mono(thio) substituted thioether 16 and di(thio) substituted thioether 17. 18 was obtained from the reaction of 16 with m-CPBA in chloroform. 9 was obtained from the reaction of l,2,3,4,4-pentachloro-(1-2-hydroxyethylthio)-1,3- butadiene 8 with 47% HI, and 11 was synthesized from the reaction of 8 with concentrated H2SO4 and KBr. Compounds 9 and 11 gave in the reaction with m-CPBA in chloroform 10, 12, and 13, respectively.