(E)-2-oxo-4-(3,4,5-trimethoxyphenyl)but-3-enoic acid methyl ester | 162087-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-oxo-4-(3,4,5-trimethoxyphenyl)but-3-enoic acid methyl ester
• 英文别名: methyl (E)-2-oxo-4-(3,4,5-trimethoxyphenyl)but-3-enoate
• CAS: 162087-77-6
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: SMBFWLCCKYRMPX-AATRIKPKSA-N

物化性质

• 沸点：
  413.5±45.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-oxo-4-(3,4,5-trimethoxyphenyl)but-3-enoic acid methyl ester 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 thallium (III) oxide 、 三氟甲磺酸 、 三氟甲磺酸酐 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 168.5h， 生成 (8R,8aR,4bS,13aS)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3-trimethoxy-11,12-methylenedioxy-7-oxa-tribenzo[a,c,e]cyclo-heptene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (E)-2-oxo-4-(3,4,5-trimethoxyphenyl)but-3-enoic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097

文献信息

• Lewis Acid Tuned Facial Stereodivergent HDA Reactions Using β-Substituted <i>N</i>-Vinyloxazolidinones
  作者：Frédéric Gohier、Keltoum Bouhadjera、Djibril Faye、Catherine Gaulon、Vincent Maisonneuve、Gilles Dujardin、Robert Dhal

  DOI：10.1021/ol062626l

  日期：2007.1.1

  R' = Me, Ar, CH2 Ar) and beta,gamma-unsaturated alpha-ketoesters (R = Ar) afforded heteroadducts with high levels of endo and facial selectivities. A complete reversal of facial differentiation was achieved by varying the Lewis acid, leading to the stereoselective formation of either endo-alpha or endo-beta adducts. [reaction: see text].

  新的β-取代的N-乙烯基-1,3-恶唑烷-2-酮（具有R'= Me，Ar，CH2 Ar）与β，γ-不饱和α-酮酸酯（[4 + 2]酸催化的杂环加成）之间（ R = Ar）提供具有高水平的内和面选择性的杂加合物。通过改变路易斯酸可以完全逆转面部分化，从而导致内-α或内-β加合物的立体选择性形成。[反应：请参见文字]。
• Lignans.19. Total synthesis of (−)-O-dimethylsugiresinol, involving asymmetric [4+2] heterocycloaddition of a styrene with a benzylidenepyruvic ester of an α-O-silyl derivative of (D)-erythronolactone
  作者：Eric Brown、Gilles Dujardin、Mickaël Maudet

  DOI：10.1016/s0040-4020(97)00646-7

  日期：1997.7

  alpha-O-t-Butyldiphenylsilyl-(D)-erythronolactone [(+/-)-25] (a new chiral vector) was esterified with 4-methoxybenzylidene pyruvic acid (19). Eu(fod)(3) catalyzed [4+2] heterocycloaddition of the latter 1-oxabutadiene with 4-methoxystyrene (as the dienophile), afforded high yields of the endo adduct 23c with 95/5 diastereofacial ratio. Five further steps led to enantiomerically pure natural (-)-O-dimethylsugiresinol (-)-2 in 12% overall yield from the acid 19. (C) 1997 Elsevier Science Ltd.
• High yield endoselective heterocycloadditions involving benzylidenepyruvic esters as the heterodiene and an alkoxystyrene as the dienophile
  作者：Gilles Dujardin、Mickaël Maudet、Eric Brown

  DOI：10.1016/s0040-4039(00)78452-8

  日期：1994.11

  The benzylidenepyruvic esters 6, 10a-d and 11 smoothly reacted with the alkoxystyrenes 12 and 13 in refluxing hexane or toluene and in the presence of catalytic amounts of Eu(fod)(3), thus selectively lending to the endo adducts 14-21 in high yields. This represents the first examples of an efficient heterocycloaddition of styrene derivatives without using the high pressure technique. The above adducts are potential intermediates for sugiresinol 7 and related tetrahydropyran neolignans.
• New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin
  作者：Mathieu Y. Laurent、Vivien Stocker、Valéry Momo Temgoua、Gilles Dujardin、Robert Dhal

  DOI：10.1016/j.tetlet.2011.01.097

  日期：2011.4

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.