ethyl (E)-6-iodo-2-hexenoate | 64277-92-5

• 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: ethyl (E)-6-iodo-2-hexenoate
• 英文别名: ethyl 6-iodo-2-hexenoate；ethyl (E)-6-iodohex-2-enoate
• CAS: 64277-92-5
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: GCNWYKRIQXHAHJ-GQCTYLIASA-N

物化性质

• 沸点：
  243.7±33.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-6-iodo-2-hexenoate 在 silver fluoride 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 ethyl 2-azatricyclo[4.4.0.0^2,8]decane-7-carboxylate
  参考文献：
  名称：

  [3 + 2]-Cycloaddition of Nonstabilized Azomethine Ylides. 10. An Efficient Strategy for the Construction of x-Azatricyclo[m.n.0.0^a,b]alkanes by Intramolecular Cycloaddition of Cyclic Azomethine Ylide

  摘要：

  [GRAPHICS]Various new structural entities related to x-azatricyclo[m.n.0.0(a,b)]alkanes are constructed by the intramolecular [3 + 2] dipolar cycloaddition of nonstabilized cyclic azomethine ylides. The ylide is generated by the sequential double desilylation of N-alkyl alpha,alpha'-bis(trimethylsilyl)cyclic amines using Ag(I)F as a one-electron oxidant.

  DOI：

  10.1021/ol006070s
• 作为产物：
  描述：

  (E)-ethyl 6-bromohex-2-enoate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以99%的产率得到ethyl (E)-6-iodo-2-hexenoate
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025

文献信息

• New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp³ Centers
  作者：Riccardo Giovannini、Thomas Stüdemann、Arokiasamy Devasagayaraj、Gaëlle Dussin、Paul Knochel

  DOI：10.1021/jo982317b

  日期：1999.5.1

  carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)(2) (7.5-10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)(2) as a catalyst (7.5-10

  在Ni（acac）（2）（在THF / NMP中为7.5-10 mol％）的情况下，卤代烷中存在不饱和键（双键，羰基，氰基）有助于其与各种二有机锌的交叉偶联反应混合物）。这些结果被用来开发新的一般的功能化二有机锌和烷基碘之间的交叉偶联反应，使用间或对三氟甲基苯乙烯作为反应促进剂，并使用Ni（acac）（2）作为催化剂（7.5-10 mol％；-35 ℃，5-10 h）导致了广泛的多功能交叉偶联产品。
• Easy preparation of a cyclobutanone ketal via a radical cyclization. The gem-dialkoxy effect
  作者：Michael E. Jung、Ivan D. Trifunovich、Nathalie Lensen

  DOI：10.1016/s0040-4039(00)61759-8

  日期：1992.11

  A new method for the facile synthesis of cyclobutanones, the key step of which is a radical cyclization to generate the four-membered ring, is reported. In addition, a comparison of the gem-dialkyl and gem-dialkoxy effects in radical cyclizations to give cyclobutane systems shows that in this system the gem-dialkoxy effect is the larger.

  报道了一种容易合成环丁酮的新方法，其关键步骤是自由基环化以生成四元环。此外，的比较宝石二烷基和宝石在自由基环化-dialkoxy效果，得到环丁烷系统示出，在该系统中的宝石-dialkoxy效果是较大的。
• a highly stereoselective synthesis of carbocyclic compounds by the michael induced intramolecular alkylation a stereocontrol of extracyclic chiral centers
  作者：Masahiko Yamaguchi、Michinori Tsukamoto、Ichiro Hirao

  DOI：10.1016/s0040-4039(00)98322-9

  日期：1985.1

  Three, five, six, and seven-membered carbocyclic compounds, some of which contain an extracyclic chiral center, were synthesized highly stereo-selectively by the Michael induced intramolecular alkylation.

  通过迈克尔诱导的分子内烷基化，高度立体选择性地合成了三元，五元，六元和七元碳环化合物，其中一些含有环外手性中心。
• <i>N</i>-(4-methylbenzenesulfonyl)- pyrrolidines and piperidines by a tandem S_N2-michael addition reaction
  作者：Richard A. Bunce、Jeffrey C. Allison

  DOI：10.1080/00397919908086214

  日期：1999.6

  A tandem S(N)2-Michael addition sequence has been developed for the preparation of N-(4-methylbenzenesulfonyl)- pyrrolidines and piperidines bearing functionalized side chains at C-2.
• Functionalized carbocycles by tandem dealkoxycarbonylation-Michael addition reactions
  作者：Richard A. Bunce、Eric D. Dowdy、Paul B. Jones、Elizabeth M. Holt

  DOI：10.1021/jo00077a043

  日期：1993.12

  A tandem dealkoxycarbonylation-Michael addition reaction has been developed as a synthetic route to highly functionalized carbocycles. Methyl esters, activated toward decarboxylation by an electron-withdrawing group at C-2 and tethered by a three- or four-carbon chain to an acrylate Michael acceptor, have been prepared and used as the cyclization substrates. Treatment of these compounds with LiCl in HMPA at 120-degrees-C or 4 h results in selective S(N)2 dealkylation of the methyl esters, decarboxylation, and cyclization of the intermediate anions by a Michael addition to the pendant acrylate moiety. This affords 45-90% of the cyclopentane- and cyclohexaneacetic esters substituted at C-2 by an electron-with drawing group. Moderate to excellent selectivity (3:1-99:1) in favor of the product having the electron-withdrawing group trans to the acetic ester side chain is observed. The reaction works best for the preparation of five-membered rings, and cyclizations proceed most cleanly from substrates which cyclize through a tertiary carbanion. Synthetic and mechanistic details as well as optimization studies and product structure proofs are presented.