4-Benzyloxy-3-hydroxymethyl-N,N-dimethyl-butyramide | 474622-91-8

• 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: 4-Benzyloxy-3-hydroxymethyl-N,N-dimethyl-butyramide
• 英文别名: 3-(hydroxymethyl)-N,N-dimethyl-4-phenylmethoxybutanamide
• CAS: 474622-91-8
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: FBWCPCPSPQZUHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Benzyloxy-3-hydroxymethyl-N,N-dimethyl-butyramide 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 甲基磺酰氯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 5-[(1S,3aR,4S,6aR)-4-(3,4-二甲氧基苯基)-1,3,3a,4,6,6a-六氢呋喃并[4,3-c]呋喃-1-基]-1,3-苯并二氧戊环
  参考文献：
  名称：

  A New Synthetic Entry to Furofuranoid Lignans, Methyl Piperitol and Fargesin

  摘要：

  An efficient and general process is described for the preparation of the unsymmetrically substituted diequatorial and axial-equatorial furofuran lignans, methyl piperitol and fargesin. The synthetic strategy is based on a stereoselective manner by nucleophilic addition of organometallic reagent to the monoterpene lactone elaborated from dihydroxyacetone dimer followed by condensation with the corresponding aromatic aldehyde counter part.

  DOI：

  10.3987/com-04-10296
• 作为产物：
  描述：

  3-羟基甲基-4-丁内酯 在 silver(l) oxide 作用下， 以 乙酸乙酯 为溶剂， 生成 4-Benzyloxy-3-hydroxymethyl-N,N-dimethyl-butyramide
  参考文献：
  名称：

  A New Synthetic Entry to Furofuranoid Lignans, Methyl Piperitol and Fargesin

  摘要：

  An efficient and general process is described for the preparation of the unsymmetrically substituted diequatorial and axial-equatorial furofuran lignans, methyl piperitol and fargesin. The synthetic strategy is based on a stereoselective manner by nucleophilic addition of organometallic reagent to the monoterpene lactone elaborated from dihydroxyacetone dimer followed by condensation with the corresponding aromatic aldehyde counter part.

  DOI：

  10.3987/com-04-10296

文献信息

• First total synthesis of a new sesquiterpenoid natural product, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone
  作者：Hidemi Yoda、Kazuhide Maruyama、Kunihiko Takabe

  DOI：10.1016/s0040-4039(03)00146-1

  日期：2003.2

  An efficient and stereodefined process is described for the first preparation of a new prenyl-benzoylfuranone type sesquiterpenoid, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone. The synthetic strategy is based on nucleophilic addition of organometallic reagents to the functionalized ketoamides elaborated from dihydroxyacetone dimer for the

  描述了一种高效且立体明确的方法，用于首次制备新的异戊二烯-苯甲酰基呋喃酮型倍半萜，（±）-3-（2,4-二羟基苯甲酰基）-4,5-二甲基-5-（4,8-二甲基-3） （E），7（E）-壬二烯-1-基）四氢-2-呋喃酮。合成策略基于将有机金属试剂亲核加成到由二羟基丙酮二聚体修饰的官能化酮酰胺上，以立体选择性地构建目标化合物中关键的季碳中心。
• First total syntheses of new phenylpropanoid lignans, (±)-aglacin k stereoisomer and (±)-arborone
  作者：M TAKAHASHI、K TAKADA、D MATSUURA、T KUNIHIKO、H YODA

  DOI：10.1016/s0385-5414(07)00052-4

  日期：2007.10.1

  An efficient and convergent process is described for the first preparation of new pherylpropanoid lignans, (+/-)-aglacin K stereoisomer and (+/-)-arborone, isolated from the stem bark of Algaia cordata and the stems of Piper arborescens, respectively. The key substituted tetrahydrofuran rings were constructed through chemoselective hydrogenation of functionalized lactol derivatives, which were in turn elaborated via requisite reverse stereoselective addition of organometallic reagent to the amide-aldehyde intermediates derived from a terpene lactone.