methyl 4,4-dimethoxy-3-methylcrotonate | 108462-68-6

• 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 4,4-dimethoxy-3-methylcrotonate
• 英文别名: methyl 4,4-dimethoxy-3-methyl-2-butenoate；Methyl 4,4-dimethoxy-3-methylbut-2-enoate；methyl 4,4-dimethoxy-3-methylbut-2-enoate
• CAS: 108462-68-6
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: XFJWNTZBOUURFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,4-dimethoxy-3-methylcrotonate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 4,4-dimethoxy-3-methyl-but-2-en-1-al
  参考文献：
  名称：

  类维生素A和相关化合物。十一。（+/-）-C22-炔属和烯丙类载脂体神经元的合成和立体化学。

  摘要：

  通过C15+C7→C22路线合成C22-乙炔和丙二烯类脱胡萝卜醛(9,17,31-34)。讨论了它们的立体结构。

  DOI：

  10.1248/cpb.36.3328
• 作为产物：
  描述：

  t-butyl 4,4-dimethoxy-3-methyl-2-butenoate 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.17h， 生成 methyl 4,4-dimethoxy-3-methylcrotonate
  参考文献：
  名称：

  Asymmetric hydrogenation of 3-methyl-fumaric and maleic ester monoaldehydes protected as neph-derived oxazolidines

  摘要：

  The hydrogenation of 3-methyl-fumaric and maleic ester mono aldehydes protected as oxazolidines of nor-ephedrine (NEPH) derivation has been studied. This transformation takes place with moderate to good pi-face stereodifferentiation and allows the preparation of non-racemic 3-methyl-succinaldehydic acid methyl ester (1, R = Me). The factors dictating the diastereocontrol are discussed.

  DOI：

  10.1016/s0040-4020(01)89738-6

文献信息

• A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds
  作者：Francesco Bonadies、Antonella Cardilli、Alessandra Lattanzi、Liliana R. Orelli、Arrigo Scettri

  DOI：10.1016/s0040-4039(00)76914-0

  日期：1994.5

  aldehydes undergo an efficient E-stereoselective Horner-Wadsworth-Emmons olefination by generation of phosphonate carbanion with lithium hydroxide. The reaction proceeds satisfactorily with linear, cyclic, polifunctional ketones in the presence of activated zeolites and and by the slow addition of the base.

  醛通过与氢氧化锂生成膦酸酯碳负离子而进行有效的E-立体选择性Horner-Wadsworth-Emmons烯化反应。在活化沸石的存在下，并通过缓慢添加碱，该反应可令人满意地用线性，环状，多官能酮进行。
• A new synthesis of Δ2-butenolides via stereoselective formation of α,β-ethylenic esters.
  作者：M. Larcheveque、Ch. Legueut、A. Debal、J.Y. Lallemand

  DOI：10.1016/s0040-4039(01)90386-7

  日期：1981.1

  A new synthesis of Δ2-butenolides is described which involves stereoselective condensation of an α-silyl ester anion with an α-ketoacetal.

  Δ的新合成2 -butenolides被描述，包括用α-ketoacetalα-甲硅烷基酯阴离子的立体选择性缩合。
• Norephedrine-derived 2-alkenyloxazolidines: stereochemistry of cyclization and allylic stereocenter directed asymmetric conjugate addition
  作者：Anna Bernardi、Silvia Cardani、Tullio Pilati、Giovanni Poli、Carlo Scolastico、Roberto Villa

  DOI：10.1021/jo00243a002

  日期：1988.4
• Asymmetric hydrogenation of 3-methyl-fumaric and maleic ester monoaldehydes protected as neph-derived oxazolidines
  作者：Anna Bernardi、Oliviero Carugo、Alessandra Pasquarello、Atanas Sidjimov、Giovanni Poli

  DOI：10.1016/s0040-4020(01)89738-6

  日期：1991.8

  The hydrogenation of 3-methyl-fumaric and maleic ester mono aldehydes protected as oxazolidines of nor-ephedrine (NEPH) derivation has been studied. This transformation takes place with moderate to good pi-face stereodifferentiation and allows the preparation of non-racemic 3-methyl-succinaldehydic acid methyl ester (1, R = Me). The factors dictating the diastereocontrol are discussed.
• Retinoids and related compounds. XI. Synthesis and stereochemistry of (.+-.)-C22-acetylenic and allenic apocarotenals.
  作者：MASAYOSHI ITO、YUMIKO HIRATA、KIYOSHI TSUKIDA、NAOKI TANAKA、KENSAKU HAMADA、RYOJI HINO、TAKAJI FUJIWARA

  DOI：10.1248/cpb.36.3328

  日期：——

  C22-Acetylenic and allenic apocarotenals (9, 17, 31-34) were synthesized by the C15+C7→C22 route. Their stereostructures are discussed.

  通过C15+C7→C22路线合成C22-乙炔和丙二烯类脱胡萝卜醛(9,17,31-34)。讨论了它们的立体结构。