1,3-bis(benzyloxymethyl)-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one | 896141-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(benzyloxymethyl)-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one
• 英文别名: 4-[(E)-3-hydroxyprop-1-enyl]-1,3-bis(phenylmethoxymethyl)imidazol-2-one
• CAS: 896141-25-6
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: HJNJHUDHVFWPDX-KPKJPENVSA-N

物化性质

• 沸点：
  540.3±60.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(benzyloxymethyl)-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one 、 (2S)-1-(4-methylphenyl)sulfonyl-2-[tri(propan-2-yl)silyloxymethyl]-2H-pyrrol-5-one 在 2,6-二甲基吡啶 作用下， 以 苯 为溶剂， 反应 17.0h， 以30%的产率得到
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068
• 作为产物：
  描述：

  1,3-bis(benzyloxymethyl)-4-(hydroxymethylene)-1,3-dihydro-imidazol-2-one 在 manganese(IV) oxide 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,3-bis(benzyloxymethyl)-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068