methyl 2-methoxycarbonyl-6,7-octadienoate | 166323-37-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-methoxycarbonyl-6,7-octadienoate
• 英文别名: dimethyl 4,5-pentadienylmalonate；dimethyl 2-(4,5-hexadienyl)malonate
• CAS: 166323-37-1
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: SIBNEYNWAYMATC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-methoxycarbonyl-6,7-octadienoate 在 碘 、 四氯化锡 、 三乙胺 作用下， 生成 dimethyl 2-iodomethyl-1-cyclohexene-3,3-dicarboxylate
  参考文献：
  名称：

  Intramolecular carbostannation reaction of active methine compounds having an allenyl group mediated by SnCl4-Et3N

  摘要：

  In the presence of SnCl4 and Et3N, intramolecular carbostannation reaction of active methine compounds having an allenyl group proceeded in a completely regioselective manner to give cyclopentene and cyclohexene derivatives in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00199-9
• 作为产物：
  描述：

  己-4,5-二烯-1-醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 2-methoxycarbonyl-6,7-octadienoate
  参考文献：
  名称：

  Acylation-cyclization of allenes using acyltetracarbonylcobalt complexes

  摘要：

  Allenes bearing tethered nucleophiles undergo acylation-cyclization on treatment with acylcobalt complexes and base.

  DOI：

  10.1016/0040-4039(94)02297-o

文献信息

• Regio- and Stereoselective Synthesis of Alkyl Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols
  作者：Zhibin Zhang、Ross A. Widenhoefer

  DOI：10.1021/ol800646h

  日期：2008.5.1

  carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio- and stereoisomer. Gold(I)-catalyzed intermolecular allene hydroalkoxylation was effective for monosubsituted, 1,1- and 1,3-disubstituted, trisubstituted, and tetrasubstituted allenes and for a range of primary and secondary alcohols, methanol, phenol, and propionic

  金（I）N-杂环卡宾配合物与AgOTf的1：1混合物在室温下催化1-苯基-1,2-丁二烯与2-苯基-1-乙醇的反应1小时，导致分离出（ E）-（3-苯乙氧基-1-丁烯基）苯作为单一的区域和立体异构体，产率为96％。金（I）催化的分子间烯丙基氢烷氧基化对于单取代的1，1-和1，3-二取代的，三取代的和四取代的烯丙基以及一系列伯和仲醇，甲醇，苯酚和丙酸是有效的。
• Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates
  作者：Lucy Curry、Michal S. Hallside、Luke H. Powell、Simon J. Sprague、Jonathan W. Burton

  DOI：10.1016/j.tet.2009.09.112

  日期：2009.12

  The regioselective synthesis of alkenylcyclanones by the oxidative radical cyclisation of malonyl radicals onto both allenes and an allylsilane is reported, along with the diastereoselective formation of [3.3.0]-bicyclic γ-lactones from two of these alkenylcyclanones. Furthermore, the cyclisation of 3-, 4- and 5-allenyl malonates on exposure to manganese(III) acetate under both oxidative and reductive

  报道了通过丙二酰基自由基在烯丙基和烯丙基硅烷上的氧化自由基环化的区域选择性合成烯基环酮，以及从这些烯基环酮中的两个非对映选择性形成[3.3.0]-双环γ-内酯。此外，据报道在氧化和还原终止条件下，暴露于乙酸锰（III）时3-，4-和5-烯丙基丙二酸酯的环化。
• Acylation-cyclization of allenes
  作者：Roderick W. Bates、Thota Rama-Devi、Huei-Huei Ko

  DOI：10.1016/0040-4020(95)00816-q

  日期：1995.11

  Allenes bearing a nucleophilic group cyclize on treatment with acyltetracarbonyl cobalt complexes in the presence of mild bases. Various nucleophilic groups and cobalt complexes can be used to give highly functionalized pyrrolidines, cyclopentanes and tetrahydrofurans. Disubstituted allenes may be used in the reaction. 1,3-disubstituted allenes give products with high stereoselectivity.
• Intramolecular and Intermolecular Mn(III)-Induced Carbon Monoxide Trapping Reactions of Alkynes with Malonate and Cyano Ester Units
  作者：Kazumi Okuro、Howard Alper

  DOI：10.1021/jo9607673

  日期：1996.1.1

  Intra- and intermolecular carbon monoxide trapping reactions of alkynes with malonates and cyano esters were developed using a Mn(III)-induced oxidative system. Phenylacetylene was treated with diethyl ethylmalonate in the presence of Mn(OAc)(3) . 2H(2)O, in AcOH-CH3CN (1:1) under carbon monoxide, affording (Z)-4,4-dicarbethoxy-2-phenyl-2-hexenoic acid. Similarly, intramolecular reactions of 4-alkynylmalonates and cyanoacetates proceeded regio- and stereoselectively under the same conditions to afford the corresponding methylenecycloalkanecarboxylic acids in moderate yields. The reaction involves carbon monoxide trapping of vinyl radicals which are formed by the addition of malonate or cyanoacetate radicals induced by Mn(III) to alkynes.
• Intramolecular Carbostannation Reaction of Active Methine Compounds with an Unactivated C−C π-Bond Mediated by SnCl₄−Et₃N
  作者：Osamu Kitagawa、Hiroki Fujiwara、Takashi Suzuki、Takeo Taguchi、Motoo Shiro

  DOI：10.1021/jo000784z

  日期：2000.10.1

  In the presence of SnCl4 and Et3N, intramolecular carbostannation reaction of various active methine compounds having an unactivated alkenyl, alkynyl, or allenyl group proceeds in good yields with complete regioselectivity. The subsequent reaction of the resulting Sn intermediates with-some electrophiles provides functionalized cyclopentane and cyclohexane derivatives.