ethyl (4R,5S)-5-but-3-enyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carboxylate | 1422042-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (4R,5S)-5-but-3-enyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carboxylate
• CAS: 1422042-42-9
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: GJKZGWGKWLUEMO-BTPDTDQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4R,5S)-5-but-3-enyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carboxylate 在 吡啶 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 barium hydroxide octahydrate 、 2,4,6-三氯苯甲酰氯 、 palladium diacetate 、 二异丁基氢化铝 、 caesium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 139.75h， 生成
  参考文献：
  名称：

  Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and syn-Selective Vinylogous Aldol Chemistry

  摘要：

  An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent Innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently In the synthesis of the C1-C15 and C16-C25 subunits, respectively.

  DOI：

  10.1021/ol400014e
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 ethyl (2R,3S)-2,3-dihydroxyhept-6-enoate 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到ethyl (4R,5S)-5-but-3-enyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and syn-Selective Vinylogous Aldol Chemistry

  摘要：

  An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent Innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently In the synthesis of the C1-C15 and C16-C25 subunits, respectively.

  DOI：

  10.1021/ol400014e

文献信息

• Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and <i>syn</i>-Selective Vinylogous Aldol Chemistry
  作者：Marilda P. Lisboa、David M. Jones、Gregory B. Dudley

  DOI：10.1021/ol400014e

  日期：2013.2.15

  An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent Innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently In the synthesis of the C1-C15 and C16-C25 subunits, respectively.