(R)-4-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-[1,3]dioxolan-2-one | 178686-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-[1,3]dioxolan-2-one
• CAS: 178686-33-4
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: XGMZKPZBLFCRSS-YNXVLUOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-[1,3]dioxolan-2-one 在 三氟乙酸 作用下， 反应 8.0h， 以90%的产率得到
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose 在 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.5h， 生成 (R)-4-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-[1,3]dioxolan-2-one
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8