Octanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide | 218924-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Octanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide
• CAS: 218924-06-2
• 化学式: C₂₉H₅₁NO₅
• 分子量: 493.728
• InChiKey: VOZMAQCQMWVXKU-ZDEZRRDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Octanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 (1S,2S,3R,6R)-6-Dioctylamino-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  Chemical modification of β-glucocerebrosidase inhibitor N -octyl-β-valienamine: synthesis and biological evaluation of N -alkanoyl and N -alkyl derivatives

  摘要：

  Several N-alkanoyl 4a-d and N-alkyl derivatives 5a-g of the potent beta-glucocerebrosidase inhibitor N-octyl beta-valienamine (3) were synthesized in order to elucidate a role of hydrophobic portion in the inhibitory action. Although the former lacked inhibitory potency, the latter were strong beta-glucocerebrosidase inhibitors (cf N-decyl-N-octyl-beta-valienamine 5d: K-i 6.6 x 10(-8) M). Furthermore, when being prescribed into mouse-derived B16 melanoma cells, N-butyl-N-octyl-beta-valienamine 5a and 5d were shown to change the amount of GlcCer and GM3, which suggests that they are possibly introduced into cells and influence glycolipids biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00143-6
• 作为产物：
  描述：

  辛酰氯 、 N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 以 吡啶 为溶剂， 反应 1.0h， 以97%的产率得到Octanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide
  参考文献：
  名称：

  Chemical modification of β-glucocerebrosidase inhibitor N -octyl-β-valienamine: synthesis and biological evaluation of N -alkanoyl and N -alkyl derivatives

  摘要：

  Several N-alkanoyl 4a-d and N-alkyl derivatives 5a-g of the potent beta-glucocerebrosidase inhibitor N-octyl beta-valienamine (3) were synthesized in order to elucidate a role of hydrophobic portion in the inhibitory action. Although the former lacked inhibitory potency, the latter were strong beta-glucocerebrosidase inhibitors (cf N-decyl-N-octyl-beta-valienamine 5d: K-i 6.6 x 10(-8) M). Furthermore, when being prescribed into mouse-derived B16 melanoma cells, N-butyl-N-octyl-beta-valienamine 5a and 5d were shown to change the amount of GlcCer and GM3, which suggests that they are possibly introduced into cells and influence glycolipids biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00143-6