(E)-methyl 3-oxo-6-nonenoate | 443957-20-8

• 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: (E)-methyl 3-oxo-6-nonenoate
• 英文别名: trans-methyl 3-oxonon-6-enoate；3-oxo-non-6t-enoic acid methyl ester；3-oxo-non-6-enoic acid methyl ester；3-Oxo-non-6t-ensaeure-methylester；3-Oxo-non-6-ensaeure-methylester；methyl (E)-3-oxonon-6-enoate
• CAS: 443957-20-8
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NAJKWSCVJAFHAO-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (E)-methyl 3-oxo-6-nonenoate 在 双(乙腈)氯化钯(II) poly(ethylene glycol) 400 、 copper dichloride 作用下， 反应 8.0h， 以90%的产率得到2-ethyl-6-oxo-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Efficient and Reusable PdCl₂(MeCN)₂/CuCl₂/PEG-400 System for Cyclization of Alkenyl β-Keto Esters and Amides

  摘要：

  PEG-400 [poly(ethylene glycol-400)] was found as an effective medium for the PdCl(2)(MeCN)(2)-catalyzed hydroalkylation cyclization of alkenyl beta-keto esters and amides. In PEG-400, no additives such as Me(3)SiCl and Ln(OTf)(3) were required for the complete conversion of alkenyl beta-keto esters. The results also showed that CuCl(2) could promote the reaction. In the presence of PdCl(2)(MeCN)(2), CuCl(2), and PEG-400, various alkenyl beta-keto esters and amides underwent a selective cyclization reaction to give good to excellent yields of the desired six-membered-ring carbocycles. Furthermore, the PdCl(2)(MeCN)(2)/CuCl(2)/PEG-400 system could be recycled and reused five times without any loss of catalytic activity.

  DOI：

  10.1021/jo0506635
• 作为产物：
  描述：

  (E)-hept-4-enoyl chloride 、 乙酰乙酸乙酯钠 在 乙醚 作用下， 生成 (E)-methyl 3-oxo-6-nonenoate
  参考文献：
  名称：

  157.合成除虫菊酯的实验。第八部分 茉莉酮的立体化学和二氢吡喃酮的身份

  摘要：

  DOI：

  10.1039/jr9520000869

文献信息

• Palladium-Catalyzed Intramolecular Hydroalkylation of Alkenyl- ?-Keto Esters, ?-Aryl Ketones, and Alkyl Ketones in the Presence of Me3SiCl or HCl
  作者：Xiaoqing Han、Xiang Wang、Tao Pei、Ross A. Widenhoefer

  DOI：10.1002/chem.200400459

  日期：2004.12.17

  palladium-catalyzed hydroalkylation, but rather served as a source of HCl, which presumably catalyzes enolization of the ketone. Identification of HCl as the active promoter of palladium-catalyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2, HCl, and CuCl2 in a sealed tube at 70 degrees C.

  3-丁烯基β-酮酸酯或3-丁烯基α-芳基酮与催化量的[PdCl2（CH3CN）2]（2）和化学计量的Me3SiCl或Me3SiCl / CuCl2在二恶烷中的反应温度为25-70摄氏度以高产率和高区域选择性生成2-取代的环己酮。该方案容许许多酯和芳基，并容许在烯丙基，烯醇，顺式和反式末端烯烃位置上的取代。原位NMR实验表明，氯硅烷并不直接参与钯催化的加氢烷基化反应，而是用作HCl的来源，推测是催化酮的烯醇化反应。
• Palladium-catalyzed cyclization of alkenyl β-keto esters in the presence of chlorotrimethylsilaneElectronic supplementary information (ESI) available: experimental procedures, analytical and spectroscopic data for new compounds and cyclohexanones. See http://www.rsc.org/suppdata/cc/b1/b111644d/
  作者：Tao Pei、Ross A. Widenhoefer

  DOI：10.1039/b111644d

  日期：2002.3.7

  PdCl2(CH3CN)2 catalyzed the cyclization of alkenyl beta-keto esters in the presence of a stoichiometric amount of SiMe3Cl to form 2-carboalkoxycyclohexanones in good yield with excellent regioselectivity.

  在化学计量的SiMe3Cl存在下，PdCl2（CH3CN）2催化了烯基β-酮酯的环化反应，从而以高收率和极佳的区域选择性形成了2-羰基烷氧基环己酮。
• Hunsdiecker, Chemische Berichte, 1942, vol. 75, p. 467
  作者：Hunsdiecker

  DOI：——

  日期：——
• US3981920A
  申请人：——

  公开号：US3981920A

  公开（公告）日：1976-09-21
• 157. Experiments on the synthesis of the pyrethrins. Part VIII. Stereochemistry of jasmone and identity of dihydropyrethrone
  作者：Leslie Crombie、Stanley H. Harper

  DOI：10.1039/jr9520000869

  日期：——