((1aS,1bR,4aR,5R,5aR)-5-Hydroxymethyl-3,3,5a-trimethyl-tetrahydro-1,2,4-trioxa-cyclopropa[a]pentalen-4a-yl)-methanol | 202402-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1aS,1bR,4aR,5R,5aR)-5-Hydroxymethyl-3,3,5a-trimethyl-tetrahydro-1,2,4-trioxa-cyclopropa[a]pentalen-4a-yl)-methanol
• 英文别名: [(1R,2S,4R,5R,6R)-6-(hydroxymethyl)-4,8,8-trimethyl-3,7,9-trioxatricyclo[4.3.0.02,4]nonan-5-yl]methanol
• CAS: 202402-56-0
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: ZJAZPAZUJWELLM-BEBVASNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((1aS,1bR,4aR,5R,5aR)-5-Hydroxymethyl-3,3,5a-trimethyl-tetrahydro-1,2,4-trioxa-cyclopropa[a]pentalen-4a-yl)-methanol 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1R,5R,6S,8R,9R)-11-benzyl-3,3,8-trimethyl-2,4,7-trioxa-11-azatetracyclo[7.3.0.01,5.06,8]dodecane
  参考文献：
  名称：

  Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]octane Building Blocks

  摘要：

  The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

  DOI：

  10.1021/np9905517
• 作为产物：
  描述：

  5,6-O-isopropylidene-2',3',4',6'-tetra-O-acetylantirrhinoside 在 sodium tetrahydroborate 、 sodium methylate 、 臭氧 作用下， 生成 ((1aS,1bR,4aR,5R,5aR)-5-Hydroxymethyl-3,3,5a-trimethyl-tetrahydro-1,2,4-trioxa-cyclopropa[a]pentalen-4a-yl)-methanol
  参考文献：
  名称：

  Ozonolysis of Protected Iridoid Glucosides

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199802)1998:2<365::aid-ejoc365>3.0.co;2-z