(4E,8E)-2-amino>-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol | 141320-88-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4E,8E)-2-amino>-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol
• 英文别名: (4E,8E)-2-[[(3E)-4,8-dimethylnona-3,7-dienyl]-methylamino]-5,9,13-trimethyltetradeca-4,8,12-trien-1-ol
• CAS: 141320-88-9
• 化学式: C₂₉H₅₁NO
• 分子量: 429.73
• InChiKey: AASSGPJLRRBDET-GMKOBWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,8E)-2-amino>-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol 在 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 甲基磺酰氯 、 三乙胺 作用下， 生成 (4E,8E)-2--5,9,13-trimethyl-4,8,12-tetradecatrien-1-yl diphosphate ammonium salt 、
  参考文献：
  名称：

  Synthesis and characterization of aza analog inhibitors of squalene and geranylgeranyl diphosphate synthases.

  摘要：

  One-carbon homologation of geranyl and farnesyl chlorides to secondary N-methylamines (12 and 17) via alpha-lithioformamidine alkylations followed by N-alkylation with bromoacetate esters afforded alpha-(homogeranylamino)-and alpha-(homofarnesylamino)acetates 13 and 18. After alpha-farnesylation of 13, hydride reductions gave branched and straight-chain tertiary beta-amino alcohols 15 and 19. The diphosphate derivatives (7 and 8) of 15 and 19 prepared by SN2 displacements may be regarded as "aza analogs" of plausible carbocation intermediates (5 and 6) in the biosynthesis of squalene and geranylgeranyl diphosphate since, in preliminary collaborative evaluations, they inhibit the respective synthase enzymes at micromolar concentrations.

  DOI：

  10.1021/jo00038a038
• 作为产物：
  描述：

  香叶基氯 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 21.5h， 生成 (4E,8E)-2-amino>-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol
  参考文献：
  名称：

  Synthesis and characterization of aza analog inhibitors of squalene and geranylgeranyl diphosphate synthases.

  摘要：

  One-carbon homologation of geranyl and farnesyl chlorides to secondary N-methylamines (12 and 17) via alpha-lithioformamidine alkylations followed by N-alkylation with bromoacetate esters afforded alpha-(homogeranylamino)-and alpha-(homofarnesylamino)acetates 13 and 18. After alpha-farnesylation of 13, hydride reductions gave branched and straight-chain tertiary beta-amino alcohols 15 and 19. The diphosphate derivatives (7 and 8) of 15 and 19 prepared by SN2 displacements may be regarded as "aza analogs" of plausible carbocation intermediates (5 and 6) in the biosynthesis of squalene and geranylgeranyl diphosphate since, in preliminary collaborative evaluations, they inhibit the respective synthase enzymes at micromolar concentrations.

  DOI：

  10.1021/jo00038a038

文献信息

• Synthesis and characterization of aza analog inhibitors of squalene and geranylgeranyl diphosphate synthases.
  作者：Arthur Steiger、Hyung Jung Pyun、Robert M. Coates

  DOI：10.1021/jo00038a038

  日期：1992.6

  One-carbon homologation of geranyl and farnesyl chlorides to secondary N-methylamines (12 and 17) via alpha-lithioformamidine alkylations followed by N-alkylation with bromoacetate esters afforded alpha-(homogeranylamino)-and alpha-(homofarnesylamino)acetates 13 and 18. After alpha-farnesylation of 13, hydride reductions gave branched and straight-chain tertiary beta-amino alcohols 15 and 19. The diphosphate derivatives (7 and 8) of 15 and 19 prepared by SN2 displacements may be regarded as "aza analogs" of plausible carbocation intermediates (5 and 6) in the biosynthesis of squalene and geranylgeranyl diphosphate since, in preliminary collaborative evaluations, they inhibit the respective synthase enzymes at micromolar concentrations.