3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide
• 英文别名: 3-oxobenzo[f]chromene-2-carboxylic acid morpholide；2-(morpholine-4-carbonyl)benzo[f]chromen-3-one
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: BJIXMRFQKGNFIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide 、 2,2-dibromo-1-phenylpropan-1-one 在 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.67h， 以56%的产率得到1-benzoyl-1-methyl-1a-morpholinocarbonyl-1a,9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-one
  参考文献：
  名称：

  Reactions of zinc enolates derived from 1-aryl-2,2-di-bromoalkanones with 2-acyl-3H-benzo[f]chromen-3-ones, 6-bromo-2-oxochromene-3-carboxamides, and 3-oxo-3H-benzo-[f]chromene-2-carboxamides

  摘要：

  由取代的1-芳基-2,2-二溴烷酮衍生的锌醇盐与2-酰基-3H-苯并[f]色烯-3-酮反应，生成1-烷基-1-酰基-1a-酰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮，以单一立体异构体的形式形成。相同的锌醇盐与6-溴-2-氧-色烯-3-氨基酸酯（哌啶类和吗啉类）反应，得到1-酰基-6-溴-1-烷基-1a-哌啶（吗啉）羰基-1a, 7b-二氢环丙烷[c]色烯-2-酮，具有高立体选择性。同样，1-苯甲酰-1-甲基-1a-吗啉羰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮是通过与3-氧-3H-苯并[f]色烯-2-羧酸吗啉的反应获得的。

  DOI：

  10.1007/s11178-005-0019-z

文献信息

• Reaction of the zinc enolate derived from 1,1-dibromo-3,3-dimethylbutan-2-one with 3-aryl-2-cyanopropenoic acid amides and esters and 2-oxochromene-3-carboxamides
  作者：V. V. Shchepin、P. S. Silaichev、Yu. G. Stepanyan、K. P. Lebedev、M. I. Vakhrin

  DOI：10.1134/s107036320605015x

  日期：2006.5

  Zinc enolate derived from 1,1-dibromo-3,3-dimethylbutan-2-one reacts with 3-aryl-2-cyanoprop2-enamides and aryl 3-aryl-2-cyanoprop-2-enoates to give the corresponding derivatives of 3-aryl-2-(2,2-dimethylpropanoyl)-1-cyanocyclopropane-1-carboxylic acid as a single stereoisomer with cis arrangement of the hydrogen atoms at the cyclopropane ring. The reactions of the same zinc enolate with 3-morpholinocarbonyl-2H-chromen-2-one and 2-morpholinocarbonyl-3H-benzo[f]chromen-3-one lead to formation of 1-(2,2dimethylpropanoyl)-1a-morpholinocarbonyl-1a,7b-dihydrocyclopropa[c]chromen-2-one and 1-(2,2-dimethylpropanoyl)-1a-morpholinocarbonyl-1a,9c-dihydrobenzo[f]cyclopropa[c]chromen-2-one, respectively as a single stereoisomer.
• Reactions of zinc enolates derived from 1-aryl-2,2-di-bromoalkanones with 2-acyl-3H-benzo[f]chromen-3-ones, 6-bromo-2-oxochromene-3-carboxamides, and 3-oxo-3H-benzo-[f]chromene-2-carboxamides
  作者：V. V. Shchepin、M. M. Kalyuzhnyi、P. S. Silaichev、N. Yu. Russkikh、R. V. Shchepin、M. A. Ezhikova、M. I. Kodess

  DOI：10.1007/s11178-005-0019-z

  日期：2004.9

  Zinc enolates derived from substituted 1-aryl-2,2-dibromoalkanones reacted with 2-acyl-3H-benzo-[f]chromen-3-ones to give 1-alkyl-1-aroyl-1a-acyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-ones which were formed as a single stereoisomer. Reactions of the same zinc enolates with 6-bromo-2-oxo-chromene-3-carboxamides (piperidides and morpholides) afforded 1-aroyl-6-bromo-1-alkyl-1a-piperidino-(morpholino)carbonyl-1a,7b-dihydrocyclopropa[c]chromen-2-ones with high stereoselectivity. Likewise, 1-benzoyl-1-methyl-1a-morpholinocarbonyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-one was obtained by reac-tion with 3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide.

  由取代的1-芳基-2,2-二溴烷酮衍生的锌醇盐与2-酰基-3H-苯并[f]色烯-3-酮反应，生成1-烷基-1-酰基-1a-酰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮，以单一立体异构体的形式形成。相同的锌醇盐与6-溴-2-氧-色烯-3-氨基酸酯（哌啶类和吗啉类）反应，得到1-酰基-6-溴-1-烷基-1a-哌啶（吗啉）羰基-1a, 7b-二氢环丙烷[c]色烯-2-酮，具有高立体选择性。同样，1-苯甲酰-1-甲基-1a-吗啉羰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮是通过与3-氧-3H-苯并[f]色烯-2-羧酸吗啉的反应获得的。