9-Decanelactam | 118162-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 9-Decanelactam
• 英文别名: 10-Methyl-2-azecanone；10-methylazecan-2-one
• CAS: 118162-68-8
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: ZMOGFOASUSPZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-Decanelactam 在 吡啶 、 nitrosonium tetrafluoroborate 作用下， 生成 phoracantholide I
  参考文献：
  名称：

  从叠氮酸到大内酰胺和大内酯

  摘要：

  据报道，有一种新方法可以在高稀释条件下，通过硫酯的形成，叠氮化物的原位还原和环化作用，将叠氮基酸转化为内酰胺。由于已经证明大内酰胺向大内酯的定量转化是可行的，因此这导致了间接的替代大内酯化过程。

  DOI：

  10.1039/c39880000270
• 作为产物：
  描述：

  10-溴癸酸 在 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium azide 、 2-硝基苯基丝氰酸酯 、 四丁基溴化铵 、 氢溴酸 、 双氧水 、 苯硒酚 、 甲基三辛基氯化铵 、 对甲苯磺酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 75.75h， 生成 9-Decanelactam
  参考文献：
  名称：

  Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam

  摘要：

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.

  DOI：

  10.1021/jo00017a027

文献信息

• Alternative procedures for the macrolactamisation of ω-Azido Acids
  作者：Imma Bosch、Pedro Romea、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(00)60653-6

  日期：1993.9

  Omega-azido acids, alter activation of the carboxyl groups as mixed anhydrides, N3(CH2)nCOOCOAr (Ar = 3,5-dinitrophenyl or 2,4,6-trichlorophenyl), can be converted to macrolactams in good yields by treatment with Bu3P under high-dilution conditions; the presence of 4-dimethylaminopyridine improves slightly the yields. Amides and peptides can be readily obtained by this procedure.
• BARTRA, MARTI;BOU, VALENTI;GARCIA, JORDI;URPI, FELIX;VILARRASA, JAUME, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 4, 270-272
  作者：BARTRA, MARTI、BOU, VALENTI、GARCIA, JORDI、URPI, FELIX、VILARRASA, JAUME

  DOI：——

  日期：——
• Cyclization of 9-substituted decanoic acid derivatives to 9-decanolide and 9-decanolactam
  作者：Marti Bartra、Jaume Vilarrasa

  DOI：10.1021/jo00017a027

  日期：1991.8

  Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedrues for lactonization and lactamization at 80-degrees-C under identical high-dilution conditions. The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed with anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions. Analogously, treatment of S-2-pyridyl 9-azidodecanethioate with Sn(SePh)3-afforded the best yield of the 10-membered lactam. The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag+ strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.
• From azido acids to macrolactams and macrolactones
  作者：Mart� Bartra、Valent� Bou、Jordi Garcia、F�lix Urpi、Jaume Vilarrasa

  DOI：10.1039/c39880000270

  日期：——

  A new method is reported for the conversion of azido acids into lactams, via thioester formation and in situ azide reduction and cyclisation under high-dilution conditions; since the quantitative conversion of macrolactams to macrolactones has been shown to be feasible, this results in an indirect, alternative macrolactonisation procedure.

  据报道，有一种新方法可以在高稀释条件下，通过硫酯的形成，叠氮化物的原位还原和环化作用，将叠氮基酸转化为内酰胺。由于已经证明大内酰胺向大内酯的定量转化是可行的，因此这导致了间接的替代大内酯化过程。