(+/-)-9-propyl-10-aza-cyclododecan-12-olide | 147363-85-7

• 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: (+/-)-9-propyl-10-aza-cyclododecan-12-olide
• 英文别名: 5-propyl-1-oxa-4-azacyclotridecan-13-one；9-n-propyl-10-azacyclododecan-12-olide；9-propyl-10-azacyclododecan-12-olide；1-Oxa-4-azacyclotridecan-13-one, 5-propyl-
• CAS: 147363-85-7
• 化学式: C₁₄H₂₇NO₂
• 分子量: 241.374
• InChiKey: QYUAIHHWMFYMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Methyl 9-oxododecanoate 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 2-氯-1-甲基吡啶碘化物 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (+/-)-9-propyl-10-aza-cyclododecan-12-olide
  参考文献：
  名称：

  Synthesis of 9-propyl-10-azacyclododecan-12-olide

  摘要：

  9-Propyl-10-azacyclododecan-12-olide, a minor component of the defensive secretion of the Mexican bean beetle (Epilachna varivestis) was synthesized via a reductive amination of methyl 9-ketododecanoate (3) followed by lactonization. This azamacrolide proved deterrent to ants, but was significantly less active than the pupal defensive secretion itself.

  DOI：

  10.1016/0040-4039(96)00233-x

文献信息

• Synthesis of a Mexican bean beetle azamacrolide allomone via a novel lactam to lactone ring expansion
  作者：Gordon W. Gribble、Richard A. Silva

  DOI：10.1016/0040-4039(96)00234-1

  日期：1996.3

  The Mixican bean beetle (Epilachna varivestis) defensive secretion azamacrolide 1 has been synthesized via the novel ring expansion of N-hydroxyethyl lactam 12, which was prepared in seven steps from cyclooctanone (6).

  通过N-羟乙基内酰胺12的新型扩环合成了Mixican豆甲虫（Epilachna varivestis）防御性分泌氮杂crocrolide 1，它是由环辛酮（7）分七个步骤制备的。
• Macrocycles by Ring-Closing Metathesis
  作者：Alois Fürstner、Klaus Langemann

  DOI：10.1055/s-1997-4472

  日期：1997.7

  The ruthenium carbene complexes 1 and 2 (0.05-5 mol%) catalyse highly efficient macrocyclization reactions of 1,ω-dienes by ring-closing metathesis (RCM). Key parameters for successful RCM are (i) the presence of a functional group which serves as a relay entity that assembles the reacting sites, (ii) an appropriate distance between this polar group and the alkenes to be metathesized, and (iii) low steric congestion near the double bonds. Contrary to previous assumptions, however, the ring size formed and the conformational predisposition of the substrates for ring closure turned out to be of minor importance. These aspects are illustrated by some straightforward syntheses of macrocyclic lactones, lactams, ethers and ketones, including the musk odored perfume ingredients Exaltolide, Exaltone and Arova 16, of the macrolide recifeiolide (24), as well as of the alkaloids epilachnene (40) and its homologue 9-propyl-10-azacyclododecan-12-olide (39), which are active principles of the defense secretions of the pupae of the mexican beetle Epilachnar varivestis .

  钌卡宾配合物1和2（0.05-5 mol%）催化通过环闭合重排（RCM）进行的高效大环化反应，涉及1,ω-二烯。成功进行RCM的关键参数为：(i) 存在一个功能团，作为中介实体，组装反应位点；(ii) 该极性基团与要重排的烯烃之间的适当距离；(iii) 双键附近较低的立体拥挤。然而，与之前的假设相反，形成的环大小和底物的环闭合构象倾向被证明重要性较小。这些方面通过一些简单的合成示例得以说明，包括大环内酯、内酰胺、醚和酮的合成，其中包括带有麝香气味的香料成分Exaltolide、Exaltone和Arova 16，以及大环药物recifeiolide (24)，以及生物碱epilachnene (40)及其同分异构体9-丙基-10-氮杂环十二烷-12-内酯 (39)，这些都是墨西哥甲虫Epilachnar varivestis蛹的防御分泌物的活性成分。
• Synthesis of novel azamacrolides (±) epilachnene and (±) 9-propyl-10-azacyclododecan-12-olide
  作者：A.V. Rama Rao、B. Venkateswara Rao、M.N. Bhanu、V. Satish Kumar

  DOI：10.1016/s0040-4039(00)76867-5

  日期：1994.5
• Synthesis of 9-propyl-10-azacyclododecan-12-olide
  作者：A.Glisan King、J. Meinwald、T. Eisner、C.L. Blankespoor

  DOI：10.1016/0040-4039(96)00233-x

  日期：1996.3

  9-Propyl-10-azacyclododecan-12-olide, a minor component of the defensive secretion of the Mexican bean beetle (Epilachna varivestis) was synthesized via a reductive amination of methyl 9-ketododecanoate (3) followed by lactonization. This azamacrolide proved deterrent to ants, but was significantly less active than the pupal defensive secretion itself.