2-{(R)-[(3aR,5R,6R,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester | 918795-20-7

• 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: 2-{(R)-[(3aR,5R,6R,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester
• CAS: 918795-20-7
• 化学式: C₁₉H₂₃BrO₇
• 分子量: 443.291
• InChiKey: AKNUTJOCKSIGGK-XSDHEKCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-{(R)-[(3aR,5R,6R,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium fluoride 作用下， 以 苯 、 乙醚 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Sequential Baylis–Hillman reaction and radical cyclization of furanose derivatives: expeditious approach to enantiopure benzo-fused nine-membered oxacycles

  摘要：

  A regioselective 9-endo-trig aryl radical cyclization of D-glucose derived diastereomeric Baylis-Hillman reaction products with Bu3SnH led to highly functionalized tricyclic benzannulated ethers incorporating cis- and trans-9,5 bicyclic systems in good yields. Degradation of one of the products afforded an enantiopure multifunctionalized benzoxonine derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.080
• 作为产物：
  描述：

  1-(6-(2-bromobenzyloxy)tetrahydro-2,2-dimethylfuro[3,2-d][1,3]dioxol-5-yl)ethane-1,2-diol 在 三乙烯二胺 、 sodium periodate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 15.0h， 生成 2-{(R)-[(3aR,5R,6R,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester
  参考文献：
  名称：

  Sequential Baylis–Hillman reaction and radical cyclization of furanose derivatives: expeditious approach to enantiopure benzo-fused nine-membered oxacycles

  摘要：

  A regioselective 9-endo-trig aryl radical cyclization of D-glucose derived diastereomeric Baylis-Hillman reaction products with Bu3SnH led to highly functionalized tricyclic benzannulated ethers incorporating cis- and trans-9,5 bicyclic systems in good yields. Degradation of one of the products afforded an enantiopure multifunctionalized benzoxonine derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.080