| 1192589-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1192589-64-2
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: JFPRZXGJMGBICH-ITFKJWCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以100%的产率得到(2R,3R,4S,6S)-2,3,4-trihydroxy-6-methylcyclohexanone
  参考文献：
  名称：

  Carbocyclization of Carbohydrates: Diastereoselective Synthesis of (+)-Gabosine F, (−)-Gabosine O, and (+)-4-epi-Gabosine O

  摘要：

  Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oximes to carbocycles furnished the first synthesis of gabosine F from L-arabinose in 12 steps with 23% overall yield, thereby confirming it absolute configuration. Similarly, efficient syntheses of gabosine O and 4-epi-gabosine O were accomplished from D-Mannose in 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regioselective dehydration, and diastereciselective hydrogenation as the key steps.

  DOI：

  10.1021/ol902071e
• 作为产物：
  描述：

  (3aR,7S,7aR)-7-hydroxy-2,2-dimethyl-5-methylidene-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-one 在 氢气 、 镍 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 10.0h， 以100 mg的产率得到
  参考文献：
  名称：

  Carbocyclization of Carbohydrates: Diastereoselective Synthesis of (+)-Gabosine F, (−)-Gabosine O, and (+)-4-epi-Gabosine O

  摘要：

  Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oximes to carbocycles furnished the first synthesis of gabosine F from L-arabinose in 12 steps with 23% overall yield, thereby confirming it absolute configuration. Similarly, efficient syntheses of gabosine O and 4-epi-gabosine O were accomplished from D-Mannose in 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regioselective dehydration, and diastereciselective hydrogenation as the key steps.

  DOI：

  10.1021/ol902071e