1-iodo-1-hexen-3-ol | 162406-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-iodo-1-hexen-3-ol
• 英文别名: 3-hydroxy-1-iodo-1-trans-hexene；(E)-1-iodohex-1-en-3-ol
• CAS: 162406-09-9
• 化学式: C₆H₁₁IO
• 分子量: 226.057
• InChiKey: CPZXMHHQFPHMKW-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-iodo-1-hexen-3-ol 在 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 22.0h， 生成 methyl 8-tert-butyldimethylsiloxy-2,4,6-undecatrienoate
  参考文献：
  名称：

  通过钯催化乙烯基卤化物，乙烯基锡化合物和降冰片二烯之间的三元偶联合成5,12-DiHETE衍生物

  摘要：

  外消旋的5,12-DiHETE-8,9-环戊二烯Diels-Alder加合物是通过钯催化乙烯基卤化物，乙烯基锡化合物和降冰片二烯之间的三元偶联制备的，收率很高。卤化物和锡链均分别通过三个和四个步骤以优异的产率合成。

  DOI：

  10.1016/0040-4020(94)00973-x
• 作为产物：
  描述：

  1-tributylstannyl-1-hexen-3-ol 在 碘 作用下， 以75%的产率得到1-iodo-1-hexen-3-ol
  参考文献：
  名称：

  通过钯催化乙烯基卤化物，乙烯基锡化合物和降冰片二烯之间的三元偶联合成5,12-DiHETE衍生物

  摘要：

  外消旋的5,12-DiHETE-8,9-环戊二烯Diels-Alder加合物是通过钯催化乙烯基卤化物，乙烯基锡化合物和降冰片二烯之间的三元偶联制备的，收率很高。卤化物和锡链均分别通过三个和四个步骤以优异的产率合成。

  DOI：

  10.1016/0040-4020(94)00973-x

文献信息

• Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogs
  作者：Fortuna Haviv、James D. Ratajczyk、Robert W. DeNet、Yvonne C. Martin、Richard D. Dyer、George W. Carter

  DOI：10.1021/jm00385a005

  日期：1987.2

  The structural requirements for inhibition of RBL-1 (rat basophilic leukemia) 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15-HETE, 1) were studied by systematic chemical modifications of the molecule at the hydroxyl and carboxyl groups, the double bonds, and the carboxylate and omega side chains. The most potent inhibitors were analogues that contained a 5,8-cis,cis-diene system and acted as alternate substrates for the enzyme. However, several analogues in which the 5,8-diene had been reduced were also found to inhibit the enzyme. Inhibition of 5-lipoxygenase by 15-hydroxyeicosa-11,13-dienoic acid (15-HEDE) analogues was optimal in compounds that generally contained a free carboxyl group, a carboxylate side chain of nine carbons, an omega side chain of five or six carbons, a cis,trans- or trans,cis-11,13-diene or 11,13-diyne system, and a 15-hydroxyl group. Conversion of 15-HEDE to its 16-membered lactone reduced but did not eliminate 5-lipoxygenase inhibitory activity. In contrast, a 3- to 10-fold enhancement of activity occurred when 5,15-diHETE (58) or 5-HETE (56) were cyclized to their respective delta-lactones. Molecular modeling of 15-HEDE analogues, modified in the C11-C15 region, showed that inactive analogues protrude into regions in space not occupied by active analogues. These structural studies indicate that multiple regions are important for 5-lipoxygenase inhibition by both 15-HETE and 15-HEDE analogues and that no single region plays a predominant role in inhibition.
• HAVIV F.; RATAJCZYK J. D.; DENET R. W.; MARTIN Y. C.; DYER R. D.; CARTER +, J. MED. CHEM., 30,(1987) N 2, 254-263
  作者：HAVIV F.、 RATAJCZYK J. D.、 DENET R. W.、 MARTIN Y. C.、 DYER R. D.、 CARTER +

  DOI：——

  日期：——
• US3962351A
  申请人：——

  公开号：US3962351A

  公开（公告）日：1976-06-08
• US3962352A
  申请人：——

  公开号：US3962352A

  公开（公告）日：1976-06-08
• US3962353A
  申请人：——

  公开号：US3962353A

  公开（公告）日：1976-06-08