(2R,3R,4S,5R)-oct-7-ene-1,2,3,4,5-pentol | 912642-25-2

• 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: (2R,3R,4S,5R)-oct-7-ene-1,2,3,4,5-pentol
• CAS: 912642-25-2
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: ZMFLKZINFYQUJM-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-oct-7-ene-1,2,3,4,5-pentol 在 四丁基碘化铵 、 sodium hydride 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 33.0h， 生成 6-O-benzyl-1,2,3-trideoxy-4,5-O-isopropylidene-D-altro-oct-1-enitol
  参考文献：
  名称：

  trans-Acetonide Controlled endo-Selective Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses:  A Facile Entry to Calystegines, Tropanes, and Hydroxylated Aminocycloheptanes

  摘要：

  High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.

  DOI：

  10.1021/ol062621o
• 作为产物：
  描述：

  D-核糖 、 3-溴丙烯 在 indium 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (2R,3R,4S,5R)-oct-7-ene-1,2,3,4,5-pentol
  参考文献：
  名称：

  trans-Acetonide Controlled endo-Selective Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses:  A Facile Entry to Calystegines, Tropanes, and Hydroxylated Aminocycloheptanes

  摘要：

  High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.

  DOI：

  10.1021/ol062621o

文献信息

• <i>trans</i>-Acetonide Controlled <i>endo</i>-Selective Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses:  A Facile Entry to Calystegines, Tropanes, and Hydroxylated Aminocycloheptanes
  作者：Tony K. M. Shing、Wai F. Wong、Taketo Ikeno、Tohru Yamada

  DOI：10.1021/ol062621o

  日期：2007.1.1

  High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.