(1R)-1-[(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol | 881302-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 881302-89-2
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: SWUCOESSUIAFQV-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 三氟甲磺酸 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 40.5h， 生成 (1R,2R,3S,7S,8S,9S)-11-benzyl-5,5-dimethyl-2-phenylmethoxy-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-8-ol
  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-木糖 在 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 (1R)-1-[(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
  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.