(3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole | 866890-79-1

• 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: (3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: (3aR,6R,6aR)-6-[(2-bromo-4,5-dimethoxyphenyl)methoxy]-2,2-dimethyl-5-methylidene-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 866890-79-1
• 化学式: C₁₇H₂₁BrO₆
• 分子量: 401.254
• InChiKey: BAOPPMQMCCKNSC-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole 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， 以67%的产率得到(3aR,3bS,10aR,11aR)-7,8-dimethoxy-2,2-dimethyl-3a,3b,5,10,10a,11a-hexahydro-1,3,4,11-tetraoxa-benzo[f]cyclopenta[a]azulene
  参考文献：
  名称：

  Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

  摘要：

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.054
• 作为产物：
  描述：

  2-溴-4,5-二甲氧基溴苄 在 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 potassium tert-butylate 、 四丁基溴化铵 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 31.5h， 生成 (3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

  摘要：

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.054

文献信息

• Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives
  作者：Arpita Neogi、Tirtha Pada Majhi、Nanda Ghoshal、Partha Chattopadhyay

  DOI：10.1016/j.tet.2005.07.054

  日期：2005.9

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.