(1S,5S,6S,8S)-8-benzyloxy-5-(imidazolylthiocarbonyl)-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol | 696598-68-2

• 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: (1S,5S,6S,8S)-8-benzyloxy-5-(imidazolylthiocarbonyl)-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol
• 英文别名: O-[(1S,5S,6S,8S)-2,2,6-trimethyl-8-phenylmethoxy-3-oxabicyclo[4.2.0]octan-5-yl] imidazole-1-carbothioate
• CAS: 696598-68-2
• 化学式: C₂₁H₂₆N₂O₃S
• 分子量: 386.515
• InChiKey: MGEZBLUDCRBEDV-TWFHAPMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,8S)-8-benzyloxy-5-(imidazolylthiocarbonyl)-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以93%的产率得到(1S,6S,8S)-8-benzyloxy-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octane
  参考文献：
  名称：

  Highly Efficient and Diastereoselective Synthesis of (+)-Lineatin

  摘要：

  A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.

  DOI：

  10.1021/ol0497032
• 作为产物：
  描述：

  (1S)-1-[(1S,4R)-4-(1-hydroxy-1-methylethyl)-1-methyl-2-cyclobutenyl]ethane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 mercury(II) diacetate 、 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.0h， 生成 (1S,5S,6S,8S)-8-benzyloxy-5-(imidazolylthiocarbonyl)-2,2,6-trimethyl-3-oxabicyclo[4.2.0]octan-5-ol
  参考文献：
  名称：

  Highly Efficient and Diastereoselective Synthesis of (+)-Lineatin

  摘要：

  A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.

  DOI：

  10.1021/ol0497032

文献信息

• Highly Efficient and Diastereoselective Synthesis of (+)-Lineatin
  作者：Ramon Alibés、Pedro de March、Marta Figueredo、Josep Font、Marta Racamonde、Teodor Parella

  DOI：10.1021/ol0497032

  日期：2004.4.1

  A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.