(1S,2S,4S)-2-(4-chlorophenylsulfonyl)-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene | 1262638-64-1

• 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: (1S,2S,4S)-2-(4-chlorophenylsulfonyl)-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene
• 英文别名: (1S,4S,5S)-5-(4-chlorophenyl)sulfonyl-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-2-ene
• CAS: 1262638-64-1
• 化学式: C₁₄H₁₅ClO₃S
• 分子量: 298.79
• InChiKey: CLEFEWWTDUNQBD-MJBXVCDLSA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  436.3±45.0 °C(predicted)
• 密度：
  1.368±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S)-2-(4-chlorophenylsulfonyl)-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium-mercury amalgam (10%) 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 ((E)-3-((2RS,5SR)-2,5-dimethyl-5-vinyltetrahydrofuran-2-yl)allyl)trimethylsilane
  参考文献：
  名称：

  Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofuransvia[4 + 2] Cycloaddition and Ring-Opening Cross-Metathesis

  摘要：

  A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed Into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.

  DOI：

  10.1021/ol102798f
• 作为产物：
  描述：

  2,5-二甲基呋喃 在 2,6-二叔丁基吡啶 、 potassium peroxomonosulfate 、 叔丁基二甲硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 30.0h， 生成 (1S,2S,4S)-2-(4-chlorophenylsulfonyl)-1,4-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofuransvia[4 + 2] Cycloaddition and Ring-Opening Cross-Metathesis

  摘要：

  A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed Into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.

  DOI：

  10.1021/ol102798f

文献信息

• Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofurans<i>via</i>[4 + 2] Cycloaddition and Ring-Opening Cross-Metathesis
  作者：Noah M. Benjamin、Stephen F. Martin

  DOI：10.1021/ol102798f

  日期：2011.2.4

  A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed Into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.