(2R,E)-2-aminooct-4-en-1-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,E)-2-aminooct-4-en-1-ol
• 英文别名: (E,2R)-2-aminooct-4-en-1-ol
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: NQYMRPAYIXOQLW-WTSVBCDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,E)-2-aminooct-4-en-1-ol 、 辛酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 为溶剂， 以90%的产率得到(2R,4E)-2-octanamido-oct-4-en-1-ol
  参考文献：
  名称：

  Ganglioside GM₃Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth

  摘要：

  An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C-8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells.

  DOI：

  10.1080/07328300600803518

文献信息

• A Study of the Calcium Complex of a Glucosylceramide, Soya-cerebroside II
  作者：Michio Kurosu、Seiji Katayama、Hirotaka Shibuya、Isao Kitagawa

  DOI：10.1248/cpb.55.1758

  日期：——

  In order to study calcium ion complex of soya-cerebroside II (1), an ionophoretic glucosylceramide isolated from soybean, C8-cerebroside (3) and 3,3″,6″-trideoxy-C8-cerebroside (4) are designed and synthesized. On the basis of extensive 1H-NMR studies in the presence of Ca2+ and a continuous variation method via 1H-NMR, soya-cerebroside II is suggested to form a calcium complex with 1/Ca2+ ratio of 1 : 1. Soya-cerebroside II serves as a tridentate chelating ligand for Ca2+; the amide carbonyl, C2′-hydroxy, and C2″-hydroxy oxygens are responsible for the Ca2+ binding. Soya-cerebroside II is structurally analogous to a neural glucosylceramide. Thus, the accumulated neural glucosylceramide inside of endoplasmic reticulum (ER) membrane may serve as an endogenous Ca2+-binding and -transport molecule (ionophore) that result in mobilization of Ca2+ from intracellular calcium stores.

  为了研究从大豆中分离出来的一种离子型葡糖基甘油酰胺--大豆脑苷脂 II（1）的钙离子络合物，设计并合成了 C8-脑苷脂（3）和 3,3″,6″-三脱氧-C8-脑苷脂（4）。大豆脑苷脂 II 是 Ca2+ 的三叉螯合配体；酰胺羰基、C2′-羟基和 C2″- 羟基氧原子负责与 Ca2+ 结合。大豆脑苷脂 II 在结构上类似于神经葡萄糖甘油酰胺。因此，内质网（ER）膜内积累的神经葡萄糖甘油酰胺可能是一种内源性 Ca2+ 结合和转运分子（ionophore），可导致从细胞内钙库中调动 Ca2+。
• Ganglioside GM₃Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth
  作者：Michio Kurosu、Isao Kitagawa

  DOI：10.1080/07328300600803518

  日期：2006.7

  An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C-8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells.