N-((R)-3-(1-hexadecyloxy)-1-hydroxypropan-2-yl)formamide | 1283128-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-((R)-3-(1-hexadecyloxy)-1-hydroxypropan-2-yl)formamide
• CAS: 1283128-71-1
• 化学式: C₂₀H₄₁NO₃
• 分子量: 343.55
• InChiKey: CFCIOZBWCHPANU-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  24.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((R)-3-(1-hexadecyloxy)-1-hydroxypropan-2-yl)formamide 在 吡啶 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (+)-3-(1-hexadecyloxy)-2-(S)-isonitrilo-1-propyl acetate
  参考文献：
  名称：

  Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk Actinocyclus papillatus

  摘要：

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.

  DOI：

  10.1021/ol200377w
• 作为产物：
  描述：

  (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-amine 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 N-((R)-3-(1-hexadecyloxy)-1-hydroxypropan-2-yl)formamide
  参考文献：
  名称：

  Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk Actinocyclus papillatus

  摘要：

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.

  DOI：

  10.1021/ol200377w