6-Phenylhex-3-en-2-amine | 212387-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Phenylhex-3-en-2-amine
• 英文别名: (E)-6-phenylhex-3-en-2-amine
• CAS: 212387-88-7
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: ZEBKQJDTEFCBOH-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-Phenylhex-3-en-2-amine 、 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005
• 作为产物：
  描述：

  (E)-1-phenylhex-4-en-3-ol 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 6-Phenylhex-3-en-2-amine
  参考文献：
  名称：

  Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

  摘要：

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.

  DOI：

  10.1021/jm00080a005

文献信息

• An Efficient Synthesis ofN-Phosphorylated Azadienes, Primary (E)-Allylamines, and β-Amino-Phosphane Oxides and -Phosphonates from β-Functionalized Oxime Derivatives
  作者：Francisco Palacios、Domitila Aparicio、Jesús García、Encina Rodríguez

  DOI：10.1002/(sici)1099-0690(199807)1998:7<1413::aid-ejoc1413>3.0.co;2-e

  日期：1998.7

  chlorides 3 to unsaturated oximes 2, while azadienes 24 are prepared by olefination reactions of functionalized enamines 20/21. Reduction of azadienes 5, 7, 24 and derivatives 13/14 and 20/21 with hydrides, followed by deprotection of the resulting amines leads to the formation of primary allylamines 1 and β-aminophosphane oxides 17, phosphonates 18, and phosphonic acid derivatives 19.

  报道了伯 (E)-烯丙胺 1 和 1-氮杂二烯 5、7 的简单立体选择性合成。N-磷酸化氮杂二烯 5 和 7 是通过将氯化磷 3 添加到不饱和肟 2 中获得的，而氮杂二烯 24 是通过官能化烯胺 20/21 的烯化反应制备的。用氢化物还原氮杂二烯 5、7、24 和衍生物 13/14 和 20/21，然后对所得胺进行脱保护，形成伯烯丙胺 1 和 β-氨基膦氧化物 17、膦酸酯 18 和膦酸衍生物 19 .