(13S)-(-)-10-oxo-13-pentadecanolide | 239801-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (13S)-(-)-10-oxo-13-pentadecanolide
• 英文别名: (14S)-14-ethyl-oxacyclotetradecane-2,11-dione
• CAS: 239801-34-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: QXZDNVMYCDSYOO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (13S)-(-)-10-oxo-13-pentadecanolide 在 儿萘酚硼烷 作用下， 反应 3.0h， 生成 (13S)-(+)-13-pentadecanolide
  参考文献：
  名称：

  Stereoselective synthesis and structural variations of ethyl analogues of galbanum macrolides

  摘要：

  Both enantiomers of 13-pentadecanolide and 15-heptadecanolide, higher analogues of galbanum macrolides, were prepared via ring enlargement of cyclodecanone and cyclododecanone, respectively. Conversion of the intermediate oxo lactones to methylenated ethyl galbanum macrolides by Wittig olefination shifted the olfactory properties dramatically. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00363-4
• 作为产物：
  描述：

  (S)-3-(tert-Butyl-dimethyl-silanyloxy)-pentanoic acid octyl ester 在 咪唑 、 N,N-二甲基丙烯基脲 、 ruthenium trichloride 、 sodium periodate 、 Amberlyst 15 、 碘 、 二异丁基氢化铝 、 三苯基膦 、 lithium diisopropyl amide 作用下， 生成 (13S)-(-)-10-oxo-13-pentadecanolide
  参考文献：
  名称：

  Stereoselective synthesis and structural variations of ethyl analogues of galbanum macrolides

  摘要：

  Both enantiomers of 13-pentadecanolide and 15-heptadecanolide, higher analogues of galbanum macrolides, were prepared via ring enlargement of cyclodecanone and cyclododecanone, respectively. Conversion of the intermediate oxo lactones to methylenated ethyl galbanum macrolides by Wittig olefination shifted the olfactory properties dramatically. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00363-4

文献信息

• Stereoselective synthesis and structural variations of ethyl analogues of galbanum macrolides
  作者：Birgit Bollbuck、Werner Tochtermann

  DOI：10.1016/s0040-4020(99)00363-4

  日期：1999.6

  Both enantiomers of 13-pentadecanolide and 15-heptadecanolide, higher analogues of galbanum macrolides, were prepared via ring enlargement of cyclodecanone and cyclododecanone, respectively. Conversion of the intermediate oxo lactones to methylenated ethyl galbanum macrolides by Wittig olefination shifted the olfactory properties dramatically. (C) 1999 Elsevier Science Ltd. All rights reserved.