tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)-methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo-[3,2-d][1,3]dioxine-7a-carboxylate | 1429481-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)-methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo-[3,2-d][1,3]dioxine-7a-carboxylate
• 英文别名: tert-butyl (4aS,6R,7R,7aS)-4a-[(E)-dodec-1-enyl]-2,2-dimethyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-6,7-dihydro-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate
• CAS: 1429481-12-8
• 化学式: C₄₀H₅₈O₇
• 分子量: 650.896
• InChiKey: RNFLSGBLMYQNTJ-OERCPSJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-叔丁基-1,3-二异丙基异脲 、 、 (1-十一烷基)三苯基鏻溴化物 在 正丁基锂 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)-methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo-[3,2-d][1,3]dioxine-7a-carboxylate 、 tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-6-((benzyloxy)-methyl)-4a-(dodec-1-enyl)tetrahydro-2,2-dimethyl-4H-furo-[3,2-d][1,3]dioxine-7a-carboxylate
  参考文献：
  名称：

  Total Synthesis of (−)-Cinatrin C₁ Based on an In(OTf)₃-Catalyzed Conia-Ene Reaction

  摘要：

  The stereocontrolled total synthesis of (-)-cinatrin C-1, a phospholipase A(2) inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)(3)-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.

  DOI：

  10.1021/jo400263w

文献信息

• Total Synthesis of (−)-Cinatrin C₁ Based on an In(OTf)₃-Catalyzed Conia-Ene Reaction
  作者：Fumiya Urabe、Shunsuke Nagashima、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1021/jo400263w

  日期：2013.4.19

  The stereocontrolled total synthesis of (-)-cinatrin C-1, a phospholipase A(2) inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)(3)-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.