((2R,3R)-3-Octadecyl-oxiranyl)-methanol | 227309-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: ((2R,3R)-3-Octadecyl-oxiranyl)-methanol
• CAS: 227309-36-6
• 化学式: C₂₁H₄₂O₂
• 分子量: 326.563
• InChiKey: YBEPZADIGAYQFL-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R)-3-Octadecyl-oxiranyl)-methanol 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium azide 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3S)-3-Amino-henicosane-1,2-diol; hydrochloride
  参考文献：
  名称：

  Synthesis, in vitro cytotoxicity and in vivo anti-inflammatory activity of long chain 3-amino-1,2-diols

  摘要：

  The synthesis of long chain 3-amino-1,2-diols was carried out based on Sharpless asymmetric epoxidation of long chain allylic alcohols and regioselective nucleophilic ring opening by azido group. The in vitro cytotoxicity of the compounds prepared was evaluated against six solid tumor cell lines (A2780, H322, LL, WiDr, C26-10, UMSCC-22B). Free 3-amino-1,2-diols exhibited IC50 values between 1.45 mu M and 32 mu M. These compound!; also presented interesting inhibition of carrageenin-induced paw edema in rats (85.3% 79.6% at a concentration of 0.15 mmol/kg). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00084-0
• 作为产物：
  描述：

  (E)-2-henicosen-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 作用下， 生成 ((2R,3R)-3-Octadecyl-oxiranyl)-methanol
  参考文献：
  名称：

  Synthesis, in vitro cytotoxicity and in vivo anti-inflammatory activity of long chain 3-amino-1,2-diols

  摘要：

  The synthesis of long chain 3-amino-1,2-diols was carried out based on Sharpless asymmetric epoxidation of long chain allylic alcohols and regioselective nucleophilic ring opening by azido group. The in vitro cytotoxicity of the compounds prepared was evaluated against six solid tumor cell lines (A2780, H322, LL, WiDr, C26-10, UMSCC-22B). Free 3-amino-1,2-diols exhibited IC50 values between 1.45 mu M and 32 mu M. These compound!; also presented interesting inhibition of carrageenin-induced paw edema in rats (85.3% 79.6% at a concentration of 0.15 mmol/kg). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00084-0