3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-N,N-dimethylbutanamide | 530098-83-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-N,N-dimethylbutanamide
• CAS: 530098-83-0
• 化学式: C₂₃H₃₃NO₃Si
• 分子量: 399.605
• InChiKey: CCHKLDZWGDUPSL-UHFFFAOYSA-N

物化性质

• 沸点：
  500.8±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-N,N-dimethylbutanamide 在 草酰氯 、 四丁基氟化铵 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one
  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 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-N,N-dimethylbutanamide
  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

• SmI2-Promoted novel tandem elimination and coupling reactions of aliphatic imides with carbonyl compounds: application to the synthesis of dl-isoretronecanol
  作者：Masayuki Kabata、Takamasa Suzuki、Kunihiko Takabe、Hidemi Yoda

  DOI：10.1016/j.tetlet.2005.12.126

  日期：2006.3

  Treatment of α-hetero-substituted cyclic imides with carbonyl compounds mediated by samarium(II) diiodide in the presence of HMPA was found to undergo novel tandem elimination and reductive coupling reactions to generate α-hydroxyalkylated imides in good to high yields. Stereochemistry of the coupling products was researched and the result that increasing the steric bulkiness of the N-substituents

  发现在HMPA存在下，用二碘化sa（II）介导的羰基化合物处理α-杂环取代的环状酰亚胺会进行新型的串联消除和还原偶联反应，从而以高至高收率生成α-羟烷基化的酰亚胺。研究了偶联产物的立体化学，并观察到增加N-取代基的立体体积导致苏式选择性增加的结果。还简要记录了这种立体选择性的机理起源，并将该反应进一步用于简单的吡咯并立烷生物碱异戊烯醇的合成。
• 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.
• A New Synthetic Entry to Furofuranoid Lignans, Methyl Piperitol and Fargesin
  作者：Hidemi Yoda、Yuji Suzuki、Daisuke Matsuura、Kunihiko Takabe

  DOI：10.3987/com-04-10296

  日期：——

  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.