methyl 3-oxo-7Z-decenoate | 71203-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 3-oxo-7Z-decenoate
• 英文别名: Methyl-Z-3-oxo-7-decenoat；methyl (Z)-3-oxodec-7-enoate
• CAS: 71203-73-1
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: QFORLGLWQDAISP-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  methyl 3-oxo-7Z-decenoate 在 magnesium(II) perchlorate 、 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以87%的产率得到
  参考文献：
  名称：

  不饱和β-酮酯的新型分子内环丙烷化反应。

  摘要：

  [反应：见正文]熔融的环丙烷β-酮酸酯是用于合成许多具有生物活性的天然产物的通用中间体。在这里，我们报告不饱和的β-酮酯的新的分子内环丙烷化反应。在I（2），Et（3）N和Lewis酸（例如Mg（ClO（4））（2）和Yb（OTf）（3））的存在下，对带有各种烯烃取代基的β-酮酯1进行了转化以高度立体定向的方式，以中等至良好的产率合成稠合的环丙烷2。还研究了反应机理。

  DOI：

  10.1021/ol0265158
• 作为产物：
  描述：

  (Z)-1-溴-3-己烯 、 乙酰乙酸甲酯 生成 methyl 3-oxo-7Z-decenoate
  参考文献：
  名称：

  Manganese(III)-based oxidative free-radical cyclization of unsaturated .beta.-keto esters, 1,3-diketones, and malonate diesters

  摘要：

  DOI：

  10.1021/jo00295a035

文献信息

• Termination of Mn(III)-Based Oxidative Cyclizations by Trapping with Azide
  作者：Barry B. Snider、Jeremy R. Duvall

  DOI：10.1021/ol049805s

  日期：2004.4.1

  The radicals formed in Mn(III)-based oxidative free-radical cyclizations of beta-keto esters and malonate esters can be trapped with sodium azide and Mn(III) to give cyclic and bicyclic azides in 30-80% yield. Reduction of the azide gives bi- and tricyclic lactams. [reaction: see text]

  β-酮基酯和丙二酸酯的基于Mn（III）的氧化自由基环化反应中形成的自由基可以用叠氮化钠和Mn（III）捕集，以30-80％的收率得到环状和双环叠氮化物。叠氮化物的还原得到双环和三环内酰胺。[反应：看文字]
• Termination of manganese(III)-based oxidative free-radical cyclizations by addition to nitriles. Formation of cyclopentanones and cyclohexanones
  作者：Barry B. Snider、Brad O. Buckman

  DOI：10.1021/jo00027a056

  日期：1992.1

  Mn(III)-based oxidative free-radical tandem cyclizations and annulations can be terminated by addition to nitriles. Cyclopentanones 20a (51%), 24a (57%), and 32a (54%) are formed in good yield. Annulation to give cyclohexanone 32b (41%) proceeds in moderate yield, although 20b (8%) and 24b (13%) are formed in poor yield in tandem cyclizations. Pyridine 39 (15%) is formed in ethanol by condensation of the enamine tautomer 37 of imine 31a with the oxidation byproduct 33a produced from radical 29a.
• Asymmetric induction in manganese(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetates and 2,5-dimethylpyrrolidine acetoacetamides
  作者：Qingwei Zhang、Raju M. Mohan、Laura Cook、Sophia Kazanis、Daniel Peisach、Bruce M. Foxman、Barry B. Snider

  DOI：10.1021/jo00079a006

  日期：1993.12

  Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90% of 13 with 86% de. Cyclization of 31b provided 56% of (+)-podocarpic acid precursor 32e with 82% de. The direction of de was opposite in these two cases. Oxidative cyclization of a-methyl beta-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while alpha-propyl beta-keto ester 44d produced a > 10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the alpha-substituent The reaction proceeds through transition states 12 and 56 with large alpha-substituents and through transition states 19 and 57 with small a-substituents. The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.
• KATES, STEVEN A.;DOMBROSKI, MARK A.;SNIDER, BARRY B., J. ORG. CHEM., 55,(1990) N, C. 2427-2436
  作者：KATES, STEVEN A.、DOMBROSKI, MARK A.、SNIDER, BARRY B.

  DOI：——

  日期：——
• SNIDER, BARRY B.;PATRICIA, JEFFREY J.;KATES, STEVEN A., J. ORG. CHEM., 53,(1988) N 10, C. 2137-2143
  作者：SNIDER, BARRY B.、PATRICIA, JEFFREY J.、KATES, STEVEN A.

  DOI：——

  日期：——