(2R,8R,12S)-12-phenyl-1-aza-10-oxatricyclo<6.4.0.0^2,6>dodec-6-en-9-one | 152972-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,8R,12S)-12-phenyl-1-aza-10-oxatricyclo<6.4.0.0^2,6>dodec-6-en-9-one
• 英文别名: (2R,8R,12R)-12-phenyl-10-oxa-1-azatricyclo[6.4.0.02,6]dodec-6-en-9-one
• CAS: 152972-17-3
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: UKFOBCOKWPTDBP-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,8R,12S)-12-phenyl-1-aza-10-oxatricyclo<6.4.0.0^2,6>dodec-6-en-9-one 在 palladium on activated charcoal 、 palladium hydroxide - carbon 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (2R,3AR,6AR)-八氢环戊二烯并[B]吡咯-2-羧酸
  参考文献：
  名称：

  Tandem generation and intramolecular trapping of chiral stabilised azomethine ylids with alkyne dipolarophiles.

  摘要：

  Due to the steric contraints imposed upon the bridging chain by the three-carbon linear unit associated with the alkyne, hex-5-ynal condenses with (5R)-phenylmorpholin-2-one (1), and undergoes intramolecular 3+2 dipolar cycloaddition via the syn- azomethine ylid to furnish adduct (2). This is in contrast to the anti-ylid pathway exhibited by the ylid derived from (1) and hept-6-ynal, which furnishes (6); or similar reactions involving alkene dipolarophilic moieties.

  DOI：

  10.1016/0040-4039(93)88116-z
• 作为产物：
  描述：

  5-己炔醛 、 (5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 在 molecular sieve 作用下， 以 甲苯 为溶剂， 以61%的产率得到(2R,8R,12S)-12-phenyl-1-aza-10-oxatricyclo<6.4.0.0^2,6>dodec-6-en-9-one
  参考文献：
  名称：

  Tandem generation and intramolecular trapping of chiral stabilised azomethine ylids with alkyne dipolarophiles.

  摘要：

  Due to the steric contraints imposed upon the bridging chain by the three-carbon linear unit associated with the alkyne, hex-5-ynal condenses with (5R)-phenylmorpholin-2-one (1), and undergoes intramolecular 3+2 dipolar cycloaddition via the syn- azomethine ylid to furnish adduct (2). This is in contrast to the anti-ylid pathway exhibited by the ylid derived from (1) and hept-6-ynal, which furnishes (6); or similar reactions involving alkene dipolarophilic moieties.

  DOI：

  10.1016/0040-4039(93)88116-z

文献信息

• Tandem generation and intramolecular trapping of chiral stabilised azomethine ylids with alkyne dipolarophiles.
  作者：Laurence M. Harwood、Lara C. Kitchen

  DOI：10.1016/0040-4039(93)88116-z

  日期：1993.10

  Due to the steric contraints imposed upon the bridging chain by the three-carbon linear unit associated with the alkyne, hex-5-ynal condenses with (5R)-phenylmorpholin-2-one (1), and undergoes intramolecular 3+2 dipolar cycloaddition via the syn- azomethine ylid to furnish adduct (2). This is in contrast to the anti-ylid pathway exhibited by the ylid derived from (1) and hept-6-ynal, which furnishes (6); or similar reactions involving alkene dipolarophilic moieties.