1a,2,6,6a-tetrahydro-1H,4H-<1,3>-dioxepino<5,6-b>azirine | 151021-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 1a,2,6,6a-tetrahydro-1H,4H-<1,3>-dioxepino<5,6-b>azirine
• 英文别名: 1a,2,6,6a-tetrahydro-1H,4H-[1,3]dioxepino[5,6-b]azirine；1a,2,6,6a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirine；(1S,7R)-3,5-dioxa-8-azabicyclo[5.1.0]octane
• CAS: 151021-81-7
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: CUMNSLGSUVVFOE-SYDPRGILSA-N

物化性质

• 沸点：
  182.0±20.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1a,2,6,6a-tetrahydro-1H,4H-<1,3>-dioxepino<5,6-b>azirine 在 吡啶 、 potassium permanganate 、 air 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 1-<(4-nitrophenyl)sulfonyl>-1a,2,6,6a-tetrahydro-1H,4H-<1,3>dioxepino<5,6-b>azirine
  参考文献：
  名称：

  Prugovecki, Biserka; Marinkovic, Marina; Vinkovic, Mladen, Croatica Chemica Acta, 2006, vol. 79, # 2, p. 219 - 226

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-6-acetylamino-5-chloro-1,3-dioxepane 在 氢氧化钾 作用下， 反应 0.25h， 以58.2%的产率得到(3aR,8aR)-2-Methyl-3a,4,8,8a-tetrahydro-[1,3]dioxepino[5,6-d]oxazole
  参考文献：
  名称：

  1-Sulfonyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirines: A novel class of fused dioxepins, potent hypoglycemic agents

  摘要：

  The new hypoglycemics, 1-sulfonyl-dioxepinoazirines 2, derived from a novel heterocyclic system, 1a,2,6,6a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirine, have been synthesized starting from trans-6-acetylamino-5-chloro-1,3-dioxepanes 7 via azirines 3. Their structure has been confirmed by the single crystal X-ray diffraction of 1-(4-acetylaminobenzenesulfonyl) derivative 2b.

  DOI：

  10.1016/s0040-4039(00)73657-4

文献信息

• Oresic, Marina; Filic, Darko; Prugovecki, Biserka, Croatica Chemica Acta, 2001, vol. 74, # 3, p. 667 - 682
  作者：Oresic, Marina、Filic, Darko、Prugovecki, Biserka、Vinkovic, Mladen、Dumic, Miljenko

  DOI：——

  日期：——
• Antihyperglycemic N-Sulfonyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]dioxepino[5,6-b]azirines: Synthesis, X-ray Structure Analysis, Conformational Behavior, Quantitative Stroposcopic Pulse Radiolysis, and Quantitative Structure-Activity Relationships
  作者：Miljenko Dumic、Mladen Vinkovic、Darko Filic、Blanka Jamnicky、Mirela Eskinja、Boris Kamenar

  DOI：10.1021/jm00016a006

  日期：1995.8

  A series of 1-sulfonyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]dioxepino[5,6-b]azirines, 4, has been synthesized and evaluated for its effects on blood glucose-decreasing activity. These derivatives were prepared from 4,7-dihydro-1,3-dioxepins 1 via vic(acylamino)halogenodioxepanes 2 and, dioxepinoazirines 3. Quantitative structure-property relationship and quantitative structure-activity relationship models, based on X-ray and molecular mechanics analyses, to our knowledge the first in the field of antihyperglycemics, were developed. They allow the prediction of properties (RP-HPLC attention times) and activities (hypoglycemic activity ratio) by the Connolly's molecular surface areas. The lead compound in these models, sulfonyldioxepinoazirine 4i, expressed superior antihyperglycemic activity in comparison to metformin in alloxanized mice, irrespective of route of application. It significantly reduced blood glucose levels in glucose-primed mice, but it did not cause a dose dependent decrease of blood glucose level in healthy (nondiabetic, control) animals.