22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-23-one | 1005277-23-5

• 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: 22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-23-one
• 英文别名: 17,19-dimethyl-6,7,9,10,16,17,19,20-octahydro-18H-16,20-epiminodibenzo[h,o][1,4,7]trioxacyclohexadecin-18-one；22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15,17,19-hexaen-23-one
• CAS: 1005277-23-5
• 化学式: C₂₃H₂₇NO₄
• mdl: MFCD07800289
• 分子量: 381.472
• InChiKey: AGAKQAUZOOAOIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-23-one 、 乙酸酐 在 吡啶 作用下， 反应 1.0h， 以76%的产率得到25-acetyl-22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0(2,7).0(15,20)]pentacosa-2,4,6,15(20),16,18-hexaen-23-one
  参考文献：
  名称：

  Transformations of dibenzo(γ-oxopiperidino)aza-14-crowns-4 upon acylation. Molecular structure of dibenzo-16-crown-3

  摘要：

  The result of acylation of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment with acetic anhydride depends on the substituent on the nitrogen atom. The NH-substrates initially undergo acylation at the piperidine nitrogen atom, followed by enolization and O-acylation. The acylation of N-methyl derivatives is accompanied by cleavage of the piperidine ring at the C-N bond with formation of acetylamino-substituted dibenzo-16-crowns-3. The Structure of the latter was determined by X-ray analysis.

  DOI：

  10.1134/s1070428008040246
• 作为产物：
  描述：

  8,9:15,16-dibenzo-11,13-dimethyl-1,4,7-trioxacyclohexadeca-8,10,12,15-tetraen-12-one 在 氨 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以73%的产率得到22,24-dimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaen-23-one
  参考文献：
  名称：

  10.1007/s11178-008-3024-1

  摘要：

  The reaction of diethyl ketone with 2-{2-[2-(2-formylphenoxy)ethoxy]ethoxy}benzaldehyde in acid medium at room temperature gave 43% of dibenzo(4-oxotetrahydropyrano)oxa-14-crown-4. The condensation of the same compounds in boiling ethanol in the presence of alkali involved cascade transformations leading to the formation of thermody namically more stable dibenzocrownophane which was assigned the structure of 8,9:15,16-dibenzo-1,4,7-trioxacyclohexadec-8,10,13,15-tetraen-12-one (yield 29%). Treatment of an alcoholic solution of the latter with gaseous ammonia or methylamine at 20C afforded 73-74% of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment.

  DOI：

  10.1007/s11178-008-3024-1

文献信息

• 10.1007/s11178-008-3023-2
  作者：Levov、An, Le Tuan、Komarova、Strokina、Soldatenkov、Khrustalev

  DOI：10.1007/s11178-008-3023-2

  日期：——
• 10.1007/s11178-008-3024-1
  作者：An, Le Tuan、Levov、Soldatenkov、Gruzdev、Khieu, Chyong Khong

  DOI：10.1007/s11178-008-3024-1

  日期：——

  The reaction of diethyl ketone with 2-2-[2-(2-formylphenoxy)ethoxy]ethoxy}benzaldehyde in acid medium at room temperature gave 43% of dibenzo(4-oxotetrahydropyrano)oxa-14-crown-4. The condensation of the same compounds in boiling ethanol in the presence of alkali involved cascade transformations leading to the formation of thermody namically more stable dibenzocrownophane which was assigned the structure of 8,9:15,16-dibenzo-1,4,7-trioxacyclohexadec-8,10,13,15-tetraen-12-one (yield 29%). Treatment of an alcoholic solution of the latter with gaseous ammonia or methylamine at 20C afforded 73-74% of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment.
• Transformations of dibenzo(γ-oxopiperidino)aza-14-crowns-4 upon acylation. Molecular structure of dibenzo-16-crown-3
  作者：A. N. Levov、An’ Le Tuan、A. T. Soldatenkov、Chyong Khong Khieu、V. N. Khrustalev

  DOI：10.1134/s1070428008040246

  日期：2008.4

  The result of acylation of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment with acetic anhydride depends on the substituent on the nitrogen atom. The NH-substrates initially undergo acylation at the piperidine nitrogen atom, followed by enolization and O-acylation. The acylation of N-methyl derivatives is accompanied by cleavage of the piperidine ring at the C-N bond with formation of acetylamino-substituted dibenzo-16-crowns-3. The Structure of the latter was determined by X-ray analysis.