benzyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate | 1267560-63-3

• 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: benzyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• 英文别名: (1S,4R)-3-benzyloxycarbonyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene；(1S,4R)-3-Benzyloxycarbonyl-2-oxa-3-azabicyclo[2.2.1]hept-5-ene；benzyl (1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS: 1267560-63-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: MXHWWBNEOOVFRU-NWDGAFQWSA-N

物化性质

• 沸点：
  357.4±32.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苄氧基乙醇 、 benzyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 在 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 benzyl N-((1S,4R)-4-(2-(benzyloxy)ethoxy)cyclopent-2-en-1-yl)-N-(hydroxy)carbamate
  参考文献：
  名称：

  [EN] SYNTHESIS OF TRIAZOLOPYRIMIDINE COMPOUNDS
  [FR] SYNTHÈSE DE COMPOSÉS DE TRIAZOLOPYRIMIDINE

  摘要：

  本发明涉及有机合成领域，描述了合成特定中间体的方法，适用于制备三唑吡咯啉类化合物，如替卡格雷。

  公开号：

  WO2013092900A1
• 作为产物：
  描述：

  N-(苄羰氧基)羟基胺 、 环戊二烯 在 2,6-二甲基吡啶 、 tris(bipyridine)ruthenium(II) dichloride hexahydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以93%的产率得到benzyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
  参考文献：
  名称：

  Accessing nitrosocarbonyl compounds with temporal and spatial control via the photoredox oxidation of N-substituted hydroxylamines

  摘要：

  Photoredox catalysis is employed to generate highly reactive acylnitroso species from hydroxamic acid derivatives. The conditions are shown to be comparable to a previously developed transition metal aerobic oxidation and are amenable to a range of transformations including Diels-Alder and ene reactions. This unique application of such an approach gives access to temporal and spatial control in nitroso chemistry. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.01.024

文献信息

• PROCESS FOR THE PREPARATION OF (1S,4R)-2-OXA-3-AZABICYCLO[2,2.1]HEPT-5-ENES
  申请人：Franzen Manuela

  公开号：US20120157671A1

  公开（公告）日：2012-06-21

  Enantiomerically enriched (1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene of formula wherein PG1 is an amino-protective group, are prepared from cyclopentadiene via hetero-Diels-Alder cycloaddition with protected 1-C-nitroso-β-D-ribofuranosyl halides of formula wherein X is a halogen atom selected from fluorine, chlorine, bromine and iodine, PG2 is a hydroxyl-protective group and PG3 is a 1,2-diol-protective group.

  通过对环戊二烯进行杂环Diels-Alder环加成反应，使用配方中PG1为氨基保护基团的保护1-C-亚硝基-β-D-核糖呋喃糖卤化物，制备富集对映体（1S,4R）-2-氧杂-3-氮杂双环[2.2.1]庚-5-烯，其中X为从氟、氯、溴和碘中选择的卤素原子，PG2为羟基保护基团，PG3为1,2-二醇保护基团。
• [EN] PROCESS FOR THE PREPARATION OF (1S,4R)-2-OXA-3-AZABICYCLO[2,2.1]HEPT-5-ENES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE (1S, 4R)-2-OXA-3-AZABICYCLO[2,2.1]HEPT-5-ÈNES
  申请人：LONZA AG

  公开号：WO2011023374A1

  公开（公告）日：2011-03-03

  Enantiomerically enriched (1 S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene of formula wherein PG1 is an amino-protective group, are prepared from cyclopentadiene via hetero-Diels-Alder cycloaddition with protected 1-C-nitroso-β-D-ribofuranosyl halides of formula wherein X is a halogen atom selected from fluorine, chlorine, bromine and iodine, PG2 is a hydroxyl-protective group and PG3 is a 1,2-diol-protective group.

  通过异构Diels-Alder环加成，从环戊二烯制备配体富集的(1 S,4R)-2-氧杂-3-氮杂双环[2.2.1]庚-5-烯，其中PG1是氨基保护基，配体的化学式如下：其中X是从氟、氯、溴和碘中选择的卤素原子，PG2是羟基保护基，PG3是1,2-二醇保护基。
• Synthesis of Triazolopyrimidine Compounds
  申请人：Lek Pharmaceuticals d.d.

  公开号：US20140371449A1

  公开（公告）日：2014-12-18

  The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

  本发明涉及有机合成领域，并描述了合成特定中间体的方法，适用于制备三唑并嘧啶类化合物，如替卡格雷。
• Cyclopropanation of nitroso Diels–Alder cycloadducts and application to the synthesis of a 2′,3′-methano carbocyclic nucleoside
  作者：Cheng Ji、Marvin J. Miller

  DOI：10.1016/j.tetlet.2010.05.062

  日期：2010.7

  Treatment of nitroso Diets-Alder cycloadducts 1 with diazomethane in the presence of palladium acetate gives synthetically useful exo-6-oxa-7-azatricyclo[3.2.1.0(2.4)]octane derivatives 7 in good to excellent yield. Using this methodology, a conformationally restricted 2',3'-methano carbocyclic nucleoside was efficiently synthesized from nitroso cycloadduct la in seven steps. (C) 2010 Elsevier Ltd. All rights reserved.
• US9278972B2
  申请人：——

  公开号：US9278972B2

  公开（公告）日：2016-03-08