(2S,3S,4R)-2,3-isopropylidenedioxy-4-benzyloxyhex-5-enal | 1312198-00-7

• 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: (2S,3S,4R)-2,3-isopropylidenedioxy-4-benzyloxyhex-5-enal
• 英文别名: (4S,5S)-2,2-dimethyl-5-[(1R)-1-phenylmethoxyprop-2-enyl]-1,3-dioxolane-4-carbaldehyde
• CAS: 1312198-00-7
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: AJKFFRYWZYTOCO-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2,3-isopropylidenedioxy-4-benzyloxyhex-5-enal 、 3-吡唑烷基氢氧氯酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(1R,2S,3R,3aS,9aR)-2,3-isopropylidenedioxy-1-benzyloxy-octahydrocyclopenta[c]pyrazol[1,2-a]pyrazolidin-7-one
  参考文献：
  名称：

  Stereoselective synthesis of polyoxygenated linear diaza-triquinanes via intramolecular 1,3-dipolar cycloaddition of sugar-derived hex-5-enals

  摘要：

  An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidin-3-one. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.031
• 作为产物：
  描述：

  (3aS,4S,6S,7S,7aS)-6-(iodomethyl)-4-methoxy-2,2-dimethyl-7-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran 在 锌 作用下， 以 乙醇 为溶剂， 生成 (2S,3S,4R)-2,3-isopropylidenedioxy-4-benzyloxyhex-5-enal
  参考文献：
  名称：

  Stereoselective synthesis of polyoxygenated linear diaza-triquinanes via intramolecular 1,3-dipolar cycloaddition of sugar-derived hex-5-enals

  摘要：

  An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidin-3-one. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.031

文献信息

• Stereoselective synthesis of polyoxygenated linear diaza-triquinanes via intramolecular 1,3-dipolar cycloaddition of sugar-derived hex-5-enals
  作者：Yunfeng Li、Yao Meng、Xiangbao Meng、Zhongjun Li

  DOI：10.1016/j.tet.2011.04.031

  日期：2011.6

  An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidin-3-one. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides
  作者：Yunfeng Li、Yao Meng、Zhongjun Li、Xiangbao Meng

  DOI：10.1016/j.tet.2015.05.105

  日期：2015.8

  An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy6-iodo-hexosides. The one-pot synthesis involves a three-step reaction, including ring-opening, condensation with tosylhydrazine, and intramolecular cycloaddition with terminal alkene, which affords important synthetic precursors of bicyclic diazenes and hydrazones. (C) 2015 Elsevier Ltd. All rights reserved.