7-acetyl-3,8-diphenyl-4a,7,8,8a-tetrahydropyrido<4,3-e>-1,4,2-dioxazine | 96212-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-acetyl-3,8-diphenyl-4a,7,8,8a-tetrahydropyrido<4,3-e>-1,4,2-dioxazine
• 英文别名: 1-((4aR*,8S*,8aS*)-3,8-diphenyl-8,8a-dihydropyrido-[4,3-e][1,4,2]dioxazin-7(4aH)-yl)ethanone；rac-1-((4aR,8S,8aS)-3,8-diphenyl-8,8a-dihydropyrido[4,3-e][1,4,2]dioxazine-7(4aH)-yl)ethanone；1-[(4aR,8S,8aS)-3,8-diphenyl-8,8a-dihydro-4aH-pyrido[4,3-e][1,4,2]dioxazin-7-yl]ethanone
• CAS: 96212-71-4
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: DBHOHURVDIEGQF-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(1S,4R,6R)-3-benzoyl-6-phenyl-2-oxa-3,5-diazabicyclo[2.2.2]oct-7-en-5-yl]ethanone 在 copper(l) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以75%的产率得到7-acetyl-3,8-diphenyl-4a,7,8,8a-tetrahydropyrido<4,3-e>-1,4,2-dioxazine
  参考文献：
  名称：

  亚硝基环加合物的异应对重排合成双环四氢吡啶酰胺和氨基甲酸酯

  摘要：

  氨基甲酸酯和酰胺亚硝基Diels-Alder环加成物与1,2-二氢吡啶的杂Cope重排反应可得到新颖的四氢吡啶烯酰胺和烯氨基甲酸酯，详细研究了最佳反应条件。当处理氨基甲酸酯亚硝基环加合物时，获得在C-4位上含有游离OH的四氢吡啶酰胺和氨基甲酸酯的可能性仅限于特定的取代方式。另一方面，从容易获得的酰胺亚硝基环加合物和催化量的亚铜盐开始，现在可以得到几种取代的4a，7,8a-四氢吡啶并[4,3- e ]-[1,4,2]二恶嗪产量中等至良好。

  DOI：

  10.1007/s10593-018-2289-8

文献信息

• Regio- and Stereodivergent Allylic Reductions of Bicyclic Piperidine Enecarbamate Derivatives
  作者：Francesco Berti、Andrea Menichetti、Lucilla Favero、Fabio Marchetti、Mauro Pineschi

  DOI：10.1021/acs.joc.8b01601

  日期：2018.10.5

  reducing agents. A completely novel, biologically active, bicyclic 1,3-diaza-4-oxa-[3.3.1]-nonene scaffold can be generated by the use of lithium triethylborohydride through unprecedented cascade syn-SN2′ reduction/carbamate reduction/cyclization reactions. The remarkable regioselectivity switches in the allylic reduction process have been rationalized with the aid of computational studies.

  1型四氢吡啶并[4,3 - e ] -1,4,2-二恶嗪的特殊性质使得可以通过常规还原剂在区域和立体选择性地获得取代的N-氨基甲酰基四氢吡啶。通过使用三乙基硼氢化锂通过空前的级联顺式-S N 2'还原/氨基甲酸酯还原/环化反应，可以生产出一种全新的，具有生物活性的双环1,3-二氮杂-4-氧杂-[3.3.1]-壬烯骨架。反应。借助于计算研究已经合理化了烯丙基还原过程中显着的区域选择性开关。
• [EN] 1,3-DIAZO-4-OXA-[3.3.1]-BICYCLIC DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND THEIR USE AS A MEDICAMENT, IN PARTICULAR FOR TREATING DIABETES<br/>[FR] DÉRIVÉS 1,3-DIAZO-4-OXA-[3.3.1]-BICYCLIQUES, PROCÉDÉ POUR LEUR FABRICATION ET LEUR UTILISATION EN TANT QUE MÉDICAMENT, EN PARTICULIER POUR LE TRAITEMENT DU DIABÈTE
  申请人：UNIV PISA

  公开号：WO2018220542A1

  公开（公告）日：2018-12-06

  The present invention relates to compounds having structural formula (I) wherein R1 and R2 are defined as set forth in the description. The invention also relates to a process for the manufacture of the above compounds of formula (I), wherein a 4a,7, 8, 8a-tetrahydropyrido[4,3-e]-1,4,2-dioxazine reacts with a hydride selected from the group consisting of: lithium triethylborohydride (LiBHEt3), sodium triethylborohydride (NaBHEt3), and lithium tetrahydroaluminate (LiAIH4), in the presence of tetrahydrofuran. Furthermore, the invention is aimed at the above compounds of formula (I), or pharmaceutically acceptable salts thereof, for use in medicine, preferably in the treatment of the diabetes and pathologies or conditions correlated thereto.

  本发明涉及具有结构式（I）的化合物，其中R1和R2的定义如描述中所述。该发明还涉及制备上述式（I）化合物的方法，其中4a，7，8，8a-四氢吡啶并[4,3-e]-1,4,2-二噁烷与选择自以下组的氢化物反应：三乙基硼氢化锂（LiBHEt3），三乙基硼氢化钠（NaBHEt3）和四氢铝酸锂（LiAIH4），在四氢呋喃的存在下。此外，本发明旨在将上述式（I）化合物或其药学上可接受的盐用于医学，优选用于糖尿病及与之相关的病理或病况的治疗。
• 1,3-diazo-4-oxa-[3.3.1]-bicyclic derivatives, process for their manufacture and their use as a medicament, in particular for treating diabetes
  申请人：UNIVERSITA' DI PISA

  公开号：US10913751B2

  公开（公告）日：2021-02-09

  The present invention relates to compounds having structural formula (I) wherein R1 and R2 are defined as set forth in the description. The invention also relates to a process for the manufacture of the above compounds of formula (I), wherein a 4a,7,8,8a-tetrahydropyrido[4,3-e]-1,4,2-dioxazine reacts with a hydride selected from the group consisting of: lithium triethylborohydride (LiBHEt3), sodium triethylborohydride (NaBHEt3), and lithium tetrahydroaluminate (LiAlH4), in the presence of tetrahydrofuran. Furthermore, the invention is aimed at the above compounds of formula (I), or pharmaceutically acceptable salts thereof, for use in medicine, preferably in the treatment of the diabetes and pathologies or conditions correlated thereto.

  本发明涉及具有结构式(I)的化合物，其中 R1 和 R2 的定义如说明书所述。本发明还涉及一种制造上述式 (I) 化合物的工艺，其中 4a,7,8,8a-四氢吡啶并[4,3-e]-1,4,2-二恶嗪与选自由以下组成的组的氢化物反应：三乙基硼氢化锂 (LiBHEt3)、三乙基硼氢化钠 (NaBHEt3) 和四氢铝酸锂 (LiAlH4)。此外，本发明的目的是将上述式（I）化合物或其药学上可接受的盐用于医药，最好是用于治疗糖尿病及与之相关的病理或病症。
• Some regio- and stereochemical aspects of the Diels-Alder reaction of nitrosocarbonyl compounds with N-substituted 1,2-dihydropyridines
  作者：Sushil K. Dubey、Edward E. Knaus

  DOI：10.1021/jo00212a015

  日期：1985.6
• 1,3-DIAZO-4-OXA-[3.3.1]-BICYCLIC DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND THEIR USE AS A MEDICAMENT, IN PARTICULAR FOR TREATING DIABETES
  申请人：Università di Pisa

  公开号：EP3630780B1

  公开（公告）日：2021-06-30