(S)-(+)-1-Phenylhexan-2-ylamine | 87982-85-2

• 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: (S)-(+)-1-Phenylhexan-2-ylamine
• 英文别名: (2S)-1-phenylhexan-2-amine
• CAS: 87982-85-2
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: UNVLUPRQPLQYGW-LBPRGKRZSA-N

物化性质

• 沸点：
  266.2±9.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-(+)-1-Phenylhexan-2-ylamine 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (S)-(+)-1-Phenylhexan-2-ylamine hydrochloride
  参考文献：
  名称：

  Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes

  摘要：

  将有机锂或格氏试剂添加到（R）或（S）-O-(1-苯基丁基)醛肟1，在三氟化硼–二乙醚的存在下，形成具有良好到优异的二烯选择性的羟胺2。随后使用锌–醋酸–超声波 cleavage N–O 键，并形成氨基甲酸酯，得到N保护的胺3，具有良好的对映体纯度（77–100% ee）。当使用烯丙基溴化镁作为有机金属试剂时，得到的羟胺被转化为β-氨基酸衍生物4和γ-氨基醇5。

  DOI：

  10.1039/a907186e
• 作为产物：
  描述：

  N-Boc-D-苯丙氨醇 在 palladium on activated charcoal 盐酸 、 sodium hypochlorite 、 氢气 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙醚 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 0.08h， 生成 (S)-(+)-1-Phenylhexan-2-ylamine
  参考文献：
  名称：

  Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.

  DOI：

  10.1021/jm0613673

文献信息

• Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes
  作者：James C. A. Hunt、Cephas Lloyd、Christopher J. Moody、Alexandra M. Z. Slawin、Andrew K. Takle

  DOI：10.1039/a907186e

  日期：——

  Addition of organolithium or Grignard reagents to (R)- or (S)-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride–diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N–O bond with zinc–acetic acid–ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77–100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-amino alcohols 5.

  将有机锂或格氏试剂添加到（R）或（S）-O-(1-苯基丁基)醛肟1，在三氟化硼–二乙醚的存在下，形成具有良好到优异的二烯选择性的羟胺2。随后使用锌–醋酸–超声波 cleavage N–O 键，并形成氨基甲酸酯，得到N保护的胺3，具有良好的对映体纯度（77–100% ee）。当使用烯丙基溴化镁作为有机金属试剂时，得到的羟胺被转化为β-氨基酸衍生物4和γ-氨基醇5。
• Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂
  作者：David A. Six、Efrosini Barbayianni、Vassilios Loukas、Violetta Constantinou-Kokotou、Dimitra Hadjipavlou-Litina、Daren Stephens、Alan C. Wong、Victoria Magrioti、Panagiota Moutevelis-Minakakis、Sharon F. Baker、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm0613673

  日期：2007.8.1

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.