(S)-dimethyl 4-(benzyloxy)-dihydro-3-methylenefuran-2,2(3H)-dicarboxylate | 1429480-82-9

• 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: (S)-dimethyl 4-(benzyloxy)-dihydro-3-methylenefuran-2,2(3H)-dicarboxylate
• 英文别名: dimethyl (4S)-3-methylidene-4-phenylmethoxyoxolane-2,2-dicarboxylate
• CAS: 1429480-82-9
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: PHDHSYDZHWXSKQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-dimethyl 4-(benzyloxy)-dihydro-3-methylenefuran-2,2(3H)-dicarboxylate 在 四氧化锇 、 正丁基锂 、 草酰氯 、 水 、 二异丁基氢化铝 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 29.0h， 生成 methyl (2S,3S,4R)-2-dodecyl-3-hydroxy-2-(hydroxymethyl)-4-phenylmethoxyoxolane-3-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：

  (S)-2-(benzyloxy)but-3-yn-1-ol 在 indium(III) triflate 、 dirhodium tetraacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 (S)-dimethyl 4-(benzyloxy)-dihydro-3-methylenefuran-2,2(3H)-dicarboxylate
  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.