7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one | 1429481-07-1

• 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: 7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one
• 英文别名: (1S,6S,8R,9R)-3,3-dimethyl-9-phenylmethoxy-8-(phenylmethoxymethyl)-2,4,7,11-tetraoxatricyclo[4.3.3.01,6]dodecan-12-one
• CAS: 1429481-07-1
• 化学式: C₂₅H₂₈O₇
• 分子量: 440.493
• InChiKey: RZOWYHOOGCXPLP-KZKYLIHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 正己烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 5.5h， 生成 tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-6-(hydroxymethyl)-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
• 作为产物：
  描述：

  在 草酰氯 、 水 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one
  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.