tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate | 1429481-16-2

• 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: tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate
• 英文别名: tert-butyl (4aS,7S,7aS)-4a-dodecyl-2,2-dimethyl-6-oxo-7-phenylmethoxy-4,7-dihydrofuro[3,2-d][1,3]dioxine-7a-carboxylate
• CAS: 1429481-16-2
• 化学式: C₃₂H₅₀O₇
• 分子量: 546.745
• InChiKey: RNHPTCFQDPAUBL-WHODAWOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 高氯酸 、 2-甲基-2-丁烯 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 27.0h， 生成
  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：

  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 在 甲醇 、 四丙基高钌酸铵 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-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.