(346/5)-1,3,4,5,6-pentachlorocyclohexene | 54083-25-9

• 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: (346/5)-1,3,4,5,6-pentachlorocyclohexene
• 英文别名: β-1,3,4,5,6-pentachlorocyclohexene；beta-Pentachlorocyclohexene；(3R,4R,5S,6R)-1,3,4,5,6-pentachlorocyclohexene
• CAS: 54083-25-9
• 化学式: C₆H₅Cl₅
• 分子量: 254.371
• InChiKey: MQYAVRUCONBHOR-FNFSYTQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (346/5)-1,3,4,5,6-pentachlorocyclohexene 在 lithium aluminium tetrahydride 、 lithium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以38.6%的产率得到(3/45)-1,3,4,5-tetrachlorocyclohexene
  参考文献：
  名称：

  Kurihara, Norio; Kohsaka, Hideo; Nakajima, Minoru, Agricultural and Biological Chemistry, 1981, vol. 45, # l2, p. 2883 - 2886

  摘要：

  DOI：
• 作为产物：
  描述：

  (36/45)-hexachlorocyclohexene 在 lithium aluminium tetrahydride 、 lithium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.75h， 以24%的产率得到(3/45)-1,3,4,5-tetrachlorocyclohexene
  参考文献：
  名称：

  Kurihara, Norio; Kohsaka, Hideo; Nakajima, Minoru, Agricultural and Biological Chemistry, 1981, vol. 45, # l2, p. 2883 - 2886

  摘要：

  DOI：

文献信息

• New Metabolites in the Degradation of α- and γ-Hexachlorocyclohexane (HCH): Pentachlorocyclohexenes Are Hydroxylated to Cyclohexenols and Cyclohexenediols by the Haloalkane Dehalogenase LinB from Sphingobium indicum B90A
  作者：Vishakha Raina、Daniel Rentsch、Thomas Geiger、Poonam Sharma、Hans Rudolf Buser、Christof Holliger、Rup Lal、Hans-Peter E. Kohler

  DOI：10.1021/jf800465q

  日期：2008.8.1

  Technical hexachlorocyclohexane (HCH) and lindane are obsolete pesticides whose former production and use led to widespread contaminations posing serious and lasting health and environmental risks. Out of nine possible stereoisomers, alpha-, beta-, gamma-, and delta-HCH are usually present at contaminated sites, and research for a better understanding of their biodegradation has become essential for the development of appropriate remediation technologies. Because haloalkane dehalogenase LinB was recently found responsible for the hydroxylation of beta-HCH, delta-HCH, and delta-pentachlorocyclohexene (delta-PCCH), we decided to examine whether beta- and gamma-PCCH, which can be formed by LinA from alpha- and gamma-HCH, respectively, were also converted by LinB. Incubation of such substrates with Escherichia coli BL21 expressing functional LinB originating from Sphingobium indicum B90A showed that both beta-PCCH and gamma-PCCH were direct substrates of LinB. Furthermore, we identified the main metabolites as 3,4,5,6-tetrachloro-2-cyclohexene-1-ols and 2,5,6-trichloro-2-cyclohexene-1,4-diols by nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry. In contrast to alpha-HCH, gamma-HCH was not a substrate for LinB. On the basis of our data, we propose a modified gamma-HCH degradation pathway in which gamma-PCCH is converted to 2,5-cyclohexadiene-1,4-diol via 3,4,5,6-tetrachloro-2-cyclohexene-1-ol and 2,5,6-trichloro-2-cyclohexene-1,4-diol.
• Kurihara, Norio; Kohsaka, Hideo; Nakajima, Minoru, Agricultural and Biological Chemistry, 1981, vol. 45, # l2, p. 2883 - 2886
  作者：Kurihara, Norio、Kohsaka, Hideo、Nakajima, Minoru

  DOI：——

  日期：——