(2E,4E,6E)-methyl 7-phenylhepta-2,4,6-trienoate | 56495-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E,6E)-methyl 7-phenylhepta-2,4,6-trienoate
• 英文别名: methyl (2E,4E,6E)-7-phenylhepta-2,4,6-trienoate；methyl 7-phenyl-2E,4E,6E-heptatrienoate；methyl 7-phenyl-2,4,6-heptatrienoate；1t-phenyl-heptatrien-(1.3t.5t)-oic acid-(7)-methyl ester；7-phenyl-hepta-2,4,6-trienoic acid methyl ester；1t-Phenyl-heptatrien-(1.3t.5t)-saeure-(7)-methylester；methyl (2E,4E,6E)-7-phenyl-2,4,6-heptatrienoate
• CAS: 56495-90-0
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: HZRVHZNFPGTNHI-PMHXHJSWSA-N

物化性质

• 沸点：
  355.6±21.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (2E,4E,6E)-methyl 7-phenylhepta-2,4,6-trienoate 以50%的产率得到5-(3-Phenyl-2-oxiranyl)-2(E),4(E)-pentadiensaeure-methylester
  参考文献：
  名称：

  Eberbach, Wolfgang; Trostmann, Uwe, Chemische Berichte, 1981, vol. 114, # 9, p. 2979 - 3003

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-bis(methylthio)-2,4-pentadienal 在 三氟化硼乙醚 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 19.0h， 生成 (2E,4E,6E)-methyl 7-phenylhepta-2,4,6-trienoate
  参考文献：
  名称：

  Asokan; Shukla; Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 10, p. 937 - 947

  摘要：

  DOI：

文献信息

• Photochemical studies on ladderane formation from conjugated esters in solution or solid phase
  作者：Vincent Mascitti、E.J. Corey

  DOI：10.1016/j.tetlet.2006.06.066

  日期：2006.8

  This letter describes a combined photochemical and X-ray crystallographic study of routes for the synthesis of cyclobutane or ladderane structures by a [2+2]-cycloaddition pathway and leads to a clearer definition of the 3-D structural requirements for such processes in the solid state.

  这封信描述了通过[2 + 2]-环加成途径合成环丁烷或梯形烷烃结构的路线的光化学和X射线晶体学组合研究，并导致对此类过程中3-D结构要求的更清晰定义。固体状态。
• Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner–Wadsworth–Emmons Olefination
  作者：Udaya Sree Dakarapu、Apparao Bokka、Parham Asgari、Gabriela Trog、Yuanda Hua、Hiep H. Nguyen、Nawal Rahman、Junha Jeon

  DOI：10.1021/acs.orglett.5b02901

  日期：2015.12.4

  A Lewis base promoted deprotonative pronucleophile addition to silyl acetals has been developed and applied to the iridium-catalyzed reductive Horner–Wadsworth–Emmons (HWE) olefination of esters and the chemoselective reduction of the resulting enoates. Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in

  已经开发了路易斯碱促进的除甲硅烷基乙缩醛外的质子化原核亲核试剂，并将其应用于铱催化的酯的霍纳-沃兹沃斯-埃蒙斯（HWE）还原性烯化反应以及所得烯酸酯的化学选择性还原。甲硅烷基乙缩醛的路易斯碱活化生成推定的五配位硅酸酯乙缩醛，其原位分解为醛，硅烷和醇盐。膦酸酯的随后去质子化金属化，然后与醛进行HWE，提供烯酸酯。该操作方便，机制独特的方案可在室温下在单个容器中将传统上具有挑战性的芳基，烯基和炔基酯转化为均一的烯酸酯。
• Oxoketene dithioacetals as versatile synthons for alternative 1,3 to 1,11 carbonyl transpositions: A new polyene synthesis
  作者：Malapaka Chandrasekharam、Chitoorthekkathil V Asokan、Hiriyakksnavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4039(00)88875-9

  日期：1990.1

  strategy for 1,7 to 1,I1 carbonyI transpositions involving 1,2 addition of sodium borohydride or Grignard reagents to polyenyl oxoketene dithioacetals obtained by condensation of bis(methylthio)polyenals 1- with active methylene ketones, followed by borontrifluoride etherate catalyzed methanolysis of the resulting polyenyl carbinol acetals to give 1,n transposed polyene esters has been described.

  1,7到1，I1羰基I换位的模型策略，涉及将1,2，H硼氢化钠或Grignard试剂加到通过将双（甲硫基）聚烯醛1-与活性亚甲基酮缩合而得到的多烯基氧杂环丁烷二硫代乙缩醛中，然后通过三氟化硼醚醚催化的甲醇分解反应已经描述了将所得的多烯基甲醇缩醛制得1，n转座的多烯酯。
• Microwave-Accelerated Ru-Catalyzed Hydrovinylation of Alkynes and Enynes: A Straightforward Approach toward 1,3-Dienes and 1,3,5-Trienes
  作者：Tobias Schabel、Bernd Plietker

  DOI：10.1002/chem.201300790

  日期：2013.5.27

  dirty! Microwave heating was found to have a significant effect on the Ru‐catalyzed hydrovinylations of alkynes. A broad range of different terminal alkynes were coupled to methyl acrylate within just 30 min in good to excellent yields (see scheme). This new protocol was transferred to the hydrovinylation of enynes as novel coupling partners in CH‐activation chemistry giving different 1,3,5‐trienes

  快速，但不脏！发现微波加热对Ru催化的炔烃氢化乙烯基化有显着影响。在短短30分钟之内即可将各种不同的末端炔烃与丙烯酸甲酯偶联，获得良好至优异的收率（参见方案）。这个新的协议转移到烯炔在C新颖偶联伴侣的hydrovinylation 给予不同的1,3,5-三烯作为唯一的产品H-激活化学。
• A novel ambident reactivity of azolylacroleins
  作者：Ildikó Nagy、György Hajós、Zsuzsanna Riedl、Orsolya Egyed、Imre Pápai

  DOI：10.1016/j.tet.2007.03.098

  日期：2007.5

  either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres.

  发现偶氮烯丙基丙烯醛与带有共轭双键的磷烷的反应在维蒂希反应中产生偶氮烯丙基，或环化成含唑取代基的二氢苯。用氮杂-维蒂希试剂转化得到四唑基吡啶。发现周围的反应性取决于磷烷的取代基，这是通过对反应中心原子电荷的从头算（DFT）计算来合理化的。