(R)-4-((1R,2S)-2-Allyloxy-1,3-dihydroxy-2-methyl-propyl)-[1,3]dioxolan-2-one | 178686-36-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-4-((1R,2S)-2-Allyloxy-1,3-dihydroxy-2-methyl-propyl)-[1,3]dioxolan-2-one
• CAS: 178686-36-7
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: MMOCWWCCYUHKTF-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((1R,2S)-2-Allyloxy-1,3-dihydroxy-2-methyl-propyl)-[1,3]dioxolan-2-one 在 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-O-allyl-1,2-O-isopropylidene-4-C-methyl-L-ribitol
  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 tetrahydroborate 、 sodium periodate 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 39.5h， 生成 (R)-4-((1R,2S)-2-Allyloxy-1,3-dihydroxy-2-methyl-propyl)-[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