(1S,2R,3R,7R,9R)-5,5,11-trimethyl-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-2-ol | 925545-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,7R,9R)-5,5,11-trimethyl-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-2-ol
• CAS: 925545-70-6
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: FHWCOHXSIWYGPT-ZOZBQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,7R,9R)-5,5,11-trimethyl-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-2-ol 在 乙酸酐 、 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 61.0h， 生成 2-benzyloxy-3-hydroxy-8-methyl-7-oxa-8-aza-bicyclo[4.2.1]nonan-4-one
  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：

  tert-butyl-dimethyl-[[(1S,2R,3S,7R,9R)-5,5,11-trimethyl-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-2-yl]oxy]silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (1S,2R,3R,7R,9R)-5,5,11-trimethyl-4,6,10-trioxa-11-azatricyclo[7.2.1.03,7]dodecan-2-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

• Stereo- and Regioselectivity in an Intramolecular Nitrone-Alkene Cycloaddition of Hept-6-enoses with a<i>trans</i>-Acetonide Blocking Group
  作者：Tony K. M. Shing、Wai F. Wong、Taketo Ikeno、Tohru Yamada

  DOI：10.1002/chem.200800867

  日期：2009.3.2

  From sugar to cycloadduct: The effect of the trans‐acetonide blocking group and the stereochemistry of the substituents on the regio‐ and stereoselectivity in the intramolecular nitrone–alkene cycloaddition (INAC) reaction of hept‐6‐enoses (see scheme) is reported and studied by using theoretical analysis.

  从糖到环加成：所述的效果的反式-acetonide封闭基团和在分子内硝酮烯烃环加成（INAC）庚-6- enoses的反应的区域选择性和立体选择性的取代基的立体化学（参见方案）被报告和通过理论分析进行研究。