1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl(piperidin-1-yl)methanone | 935467-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl(piperidin-1-yl)methanone
• CAS: 935467-61-1
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: YIMLLJWYKURRLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl(piperidin-1-yl)methanone 在 四甲基乙二胺 、 仲丁基锂 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.17h， 生成 6-(Dimethylamino)-3-tellura-17-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-1(21),2(11),4(9),5,7,12-hexaen-10-one
  参考文献：
  名称：

  微波辅助合成Julolidine-9-羧酰胺衍生物的合成及其通过定向金属转化为硫属黄嘌呤的方法

  摘要：

  通过微波辅助的Willgerodt-Kindler反应将9-甲酰基甲氧萘啶氧化为N-哌啶或N-吗啉朱螺啶-9-硫酰胺。9-甲酰基-1,1,7,7-四甲基甲氧萘啶得到相应的N-哌啶四甲基甲氧吡啶-9-硫酰胺。用三氟乙酸酐将硫代酰胺转化为相应的羧酰胺。酰胺基团在聚ul啶体系中定向原位金属化，但不在四甲基聚ul啶体系中。生成的阴离子被二卤化原电子亲电试剂捕获。用三氯氧磷和三乙胺（POCl 3 / Et 3 N）将所得产物转化为硫属黄嘌呤。

  DOI：

  10.1021/jo070086f
• 作为产物：
  描述：

  9-醛基久洛尼定 在 sulfur 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl(piperidin-1-yl)methanone
  参考文献：
  名称：

  微波辅助合成Julolidine-9-羧酰胺衍生物的合成及其通过定向金属转化为硫属黄嘌呤的方法

  摘要：

  通过微波辅助的Willgerodt-Kindler反应将9-甲酰基甲氧萘啶氧化为N-哌啶或N-吗啉朱螺啶-9-硫酰胺。9-甲酰基-1,1,7,7-四甲基甲氧萘啶得到相应的N-哌啶四甲基甲氧吡啶-9-硫酰胺。用三氟乙酸酐将硫代酰胺转化为相应的羧酰胺。酰胺基团在聚ul啶体系中定向原位金属化，但不在四甲基聚ul啶体系中。生成的阴离子被二卤化原电子亲电试剂捕获。用三氯氧磷和三乙胺（POCl 3 / Et 3 N）将所得产物转化为硫属黄嘌呤。

  DOI：

  10.1021/jo070086f

文献信息

• Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines
  作者：Mark W. Kryman、Gregory A. Schamerhorn、Jacqueline E. Hill、Brandon D. Calitree、Kellie S. Davies、Michelle K. Linder、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1021/om500346j

  日期：2014.5.27

  Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two "half-julolidine" groups (a trimethyltetrahydroquinoline) and one julolidine and one "half-julolidine" were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (O-1(2)) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths >= 690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidized in vitro to the fluorescent telluroxide.
• A Microwave-Assisted Synthesis of Julolidine-9-carboxamide Derivatives and Their Conversion to Chalcogenoxanthones via Directed Metalation
  作者：Jason J. Holt、Brandon D. Calitree、Josiah Vincek、Michael K. Gannon、Michael R. Detty

  DOI：10.1021/jo070086f

  日期：2007.3.1

  7-tetramethyljulolidine gave the corresponding N-piperidine tetramethyljulolidine-9-thioamide. The thioamides were converted to the corresponding carboxamides with trifluoroacetic anhydride. The amide group directed ortho-metalation in the julolidine system, but not in the tetramethyljulolidine system. The resulting anion was captured by dichalcogenide electrophiles. The resulting products were converted to chalcogenoxanthones

  通过微波辅助的Willgerodt-Kindler反应将9-甲酰基甲氧萘啶氧化为N-哌啶或N-吗啉朱螺啶-9-硫酰胺。9-甲酰基-1,1,7,7-四甲基甲氧萘啶得到相应的N-哌啶四甲基甲氧吡啶-9-硫酰胺。用三氟乙酸酐将硫代酰胺转化为相应的羧酰胺。酰胺基团在聚ul啶体系中定向原位金属化，但不在四甲基聚ul啶体系中。生成的阴离子被二卤化原电子亲电试剂捕获。用三氯氧磷和三乙胺（POCl 3 / Et 3 N）将所得产物转化为硫属黄嘌呤。