Methyl (E,E)-6-phenylhexa-3,5-dienoate | 79994-37-9

• 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: Methyl (E,E)-6-phenylhexa-3,5-dienoate
• 英文别名: methyl 6-phenyl-3,5-hexadienylcarboxylate；methyl (3E,5E)-6-phenylhexa-3,5-dienoate
• CAS: 79994-37-9
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: UQZCDMYUWPQJOH-ASVGJQBISA-N

物化性质

• 沸点：
  324.0±21.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  Methyl (E,E)-6-phenylhexa-3,5-dienoate 在 dirhodium tetraacetate 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 methyl (3E,5E)-6-phenyl-2-(dimethylphenylsilyl)hexa-3,5-dienoate
  参考文献：
  名称：

  铑（II）-乙烯基类胡萝卜素插入SiH键中。烯丙基硅烷的立体定向合成的新方法

  摘要：

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。

  DOI：

  10.1016/0040-4039(94)88508-7
• 作为产物：
  描述：

  (E)-6-Phenyl-3-tosyl-5-hexenoic acid 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl (E,E)-6-phenylhexa-3,5-dienoate
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043

文献信息

• Synthesis of substituted hexa-3,5-dienoic acid methyl esters from conjugated dienones
  作者：Rishan Lang Nongkhlaw、Ridaphun Nongrum、Bekington Myrboh

  DOI：10.1039/b101242h

  日期：——

  Substituted hexa-3,5-dienoic acid methyl esters (2) were conveniently prepared in one step by 1,2-carbonyl transposition of the corresponding dienones (1) using lead(IV) acetate and boron trifluoride–diethyl ether in benzene at room temperature.

  室温下，在苯中使用乙酸铅（IV）和三氟化硼二乙醚，通过 1,2-羰基转位相应的二烯酮（1），一步即可方便地制备出取代的六-3,5-二烯酸甲酯（2）。
• Rearrangement studies on 3,3-bis(methylthio)-1-(arylcyclopropyl) -2-propen-1-ols: Synthesis of functionalized cyclopentenes and polyene esters
  作者：Balaram Patro、Bishwajit Deb、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)80748-1

  日期：1994.4

  The cyclopropyl carbinols 8 and 9 obtained by either borohydride reduction (or Grignard addition) of the cyclopropyl ketones 1 are shown to undergo acid induced ring opening and intramolecular cyclization (5-exo or 6-endo) or deprotonation to afford either cyclopentene, biphenyl or conjugated polyene derivatives depending on the nature of Lewis acid, reaction conditions and the structuralfeatures present

  通过环丙基酮1的硼氢化物还原（或格氏加成反应）获得的环丙基甲醇8和9被显示为发生酸诱导的开环和分子内环化（5-外部或6-内基）或去质子化，从而提供环戊烯，联苯或共轭多烯衍生物，取决于路易斯酸的性质，反应条件和环丙基甲醇中存在的结构特征。已经提出了形成各种产物的可能机理。
• Pivotal Role of (<i>E</i>)-3-Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions: Synthesis of (<i>3E</i>,<i>5E</i>)- and (<i>3E</i>,<i>5Z</i>)-6-Phenyl-3,5-hexadienoic Acid
  作者：Takeshi Sugai、Masahiro Yokoyama、Takahiro Yamazaki、Hiromichi Ohta

  DOI：10.1246/cl.1997.797

  日期：1997.8

  The first example of the enzyme-catalyzed hydrolysis of a nitrile bearing alkenylboronic acid functionality and its application to the synthesis of dienecarboxylic acids are described. (E)-3-Carbamoyl-1-propenylboronic acid was obtained by an incubation of the corresponding nitrile with Rhodococcus rhodochrous IFO 15564. Palladium(0)-catalyzed cross-coupling reaction of the product with (E)- and (Z)-bromoalkenes afforded the (3E,5E)- and (3E,5Z)-unsaturated amides, respectively. The second incubation of the above amides with the same microorganism provided the carboxylic acids with the defined configuration of conjugated double bonds.

  本文介绍了酶催化水解带有烯基硼酸官能团的腈的第一个实例及其在合成二烯羧酸中的应用。(E)-3-Carbamoyl-1-propenylboronic acid 是通过相应的腈与 Rhodococcus rhodochrous IFO 15564 培养得到的。在钯（0）催化下，产物与(E)-和(Z)-溴烯发生交叉偶联反应，分别得到(3E,5E)-和(3E,5Z)-不饱和酰胺。将上述酰胺与同一微生物进行第二次培养，可得到具有共轭双键定义构型的羧酸。
• Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates
  作者：Youichi Ishii、Chao Gao、Wen Xiang Xu、Masakazu Iwasaki、Masanobu Hidai

  DOI：10.1021/jo00076a051

  日期：1993.11

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.
• Patro Balaram, Deb Bishwajit, Ila Hiriyakkanavar, Junjappa Hiriyakkanavar, Tetrahedron, 50 (1994) N 1, S 255-264
  作者：Patro Balaram, Deb Bishwajit, Ila Hiriyakkanavar, Junjappa Hiriyakkanavar

  DOI：——

  日期：——