(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (Z)-2-trimethylsilanyloxy-vinyl ester | 850835-73-3

• 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)-3-(4-Benzyloxy-phenyl)-acrylic acid (Z)-2-trimethylsilanyloxy-vinyl ester
• 英文别名: [(Z)-2-trimethylsilyloxyethenyl] (E)-3-(4-phenylmethoxyphenyl)prop-2-enoate
• CAS: 850835-73-3
• 化学式: C₂₁H₂₄O₄Si
• 分子量: 368.505
• InChiKey: FFNSWTQJVSSGIN-ILGRFDKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (Z)-2-trimethylsilanyloxy-vinyl ester 、 (2R,3R)-3-hydroxy-2,3-bis(benzylyloxy)propionaldehyde 在 magnesium bromide 作用下， 以 甲苯 为溶剂， 反应 30.5h， 生成 (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2R,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2,4-dihydroxy-tetrahydro-pyran-3-yl ester 、 (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2,4-dihydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Total Synthesis of Brasoside and Littoralisone

  摘要：

  The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

  DOI：

  10.1021/ja050064f
• 作为产物：
  描述：

  (E)-2-hydroxyethyl 3-(4-(benzyloxy)phenyl)acrylate 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (Z)-2-trimethylsilanyloxy-vinyl ester
  参考文献：
  名称：

  Total Synthesis of Brasoside and Littoralisone

  摘要：

  The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

  DOI：

  10.1021/ja050064f