(Z)-17-tert-Butoxycarbonylamino-octadec-9-enoic acid | 932390-27-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-17-tert-Butoxycarbonylamino-octadec-9-enoic acid
• CAS: 932390-27-7
• 化学式: C₂₃H₄₃NO₄
• 分子量: 397.599
• InChiKey: YDGQRAKPZTXDLI-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  28.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-17-tert-Butoxycarbonylamino-octadec-9-enoic acid 、 叔丁醇 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以107 mg的产率得到((Z)-16-tert-Butoxycarbonylamino-heptadec-8-enyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  由槐糖脂衍生的17-羟基油酸合成多官能脂肪胺

  摘要：

  AbstractA series of mono‐ and diamines and one triamine have been prepared using methyl 17‐hydroxy oleate as the common starting material. The 17‐hydroxy oleate is an abundant bioderived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural by‐products. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions used are allylic bromination, Curtius rearrangement, and the Mitsunobu reaction. These fatty amines also possess functionality such as hydroxy groups, carboxylic acids, and C−C double bonds. The amines are isolated in protected form using a variety of protecting groups, the identities of which can be selected on the basis of the intended use of the amine. These novel compounds will be of interest in the preparation of highly functionalized polymers and surfactants, among other areas.

  DOI：

  10.1007/s11746-006-1248-1
• 作为产物：
  描述：

  methyl 17-hydroxyoleate 在 lithium hydroxide 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 72.0h， 生成 (Z)-17-tert-Butoxycarbonylamino-octadec-9-enoic acid
  参考文献：
  名称：

  由槐糖脂衍生的17-羟基油酸合成多官能脂肪胺

  摘要：

  AbstractA series of mono‐ and diamines and one triamine have been prepared using methyl 17‐hydroxy oleate as the common starting material. The 17‐hydroxy oleate is an abundant bioderived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural by‐products. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions used are allylic bromination, Curtius rearrangement, and the Mitsunobu reaction. These fatty amines also possess functionality such as hydroxy groups, carboxylic acids, and C−C double bonds. The amines are isolated in protected form using a variety of protecting groups, the identities of which can be selected on the basis of the intended use of the amine. These novel compounds will be of interest in the preparation of highly functionalized polymers and surfactants, among other areas.

  DOI：

  10.1007/s11746-006-1248-1