(1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.0^2,4]octan-7-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧哌啶
• 英文名称: (1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.0^2,4]octan-7-one
• 英文别名: 2-azabicyclo<2.2.1>hept-5-en-3-one epoxide；5,6-exo-Epoxy-2-azabicyclo<2.2.1>heptan-3-one；(±)-cis-5,6-epoxy-2-azabicyclo[2.2.1]heptan-3-one；(1R,2S,4R,5S)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: CSUABHOMDQBGFZ-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.0^2,4]octan-7-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.5h， 生成 (+/-)-2α,3α-Epoxy-4β-hydroxymethyl-1β-cyclopentane
  参考文献：
  名称：

  Synthesis of Nucleosides and Related Compounds. XXII. Carbocyclic Analogues of Thymidine and Related Compounds from 2-Azabicyclo(2.2.1)hept-5-en-3-ones.

  摘要：

  还原性酰胺键断裂反应，我们实验室之前已详细研究，用于从易得的2-氮杂双环[2.2.1]庚-5-烯-3-酮合成碳环核糖胸苷，成功应用于碳环核糖胸苷及相关化合物的合成。

  DOI：

  10.1248/cpb.39.1682
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以59%的产率得到(1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.0^2,4]octan-7-one
  参考文献：
  名称：

  Synthesis of Nucleosides and Related Compounds. XXII. Carbocyclic Analogues of Thymidine and Related Compounds from 2-Azabicyclo(2.2.1)hept-5-en-3-ones.

  摘要：

  还原性酰胺键断裂反应，我们实验室之前已详细研究，用于从易得的2-氮杂双环[2.2.1]庚-5-烯-3-酮合成碳环核糖胸苷，成功应用于碳环核糖胸苷及相关化合物的合成。

  DOI：

  10.1248/cpb.39.1682

文献信息

• Metal-Catalyzed Reactions between 2-Azabicyclo[2.2.1]hept-5-en-3-ones and Arylboronic Acids
  作者：Takumi Abe、Hiroyuki Takeda、Yumi Takahashi、Yoshihisa Miwa、Koji Yamada、Minoru Ishikura

  DOI：10.1002/ejoc.201000135

  日期：2010.6

  Cu- and Rh-catalyzed coupling reactions of 2-azabicyclo[2.2.1]hept-5-en-3-ones (1) with arylboronic acids were successful carried out under microwave irradiation conditions and yielded N-aryl and C-aryl derivatives of 1, respectively.

  Cu-和Rh-催化的2-氮杂双环[2.2.1]hept-5-en-3-ones (1)与芳基硼酸的偶联反应在微波辐射条件下成功进行，得到N-芳基和C-芳基衍生物分别为 1。
• 2-Azabicyclo[2.2.1]hept-5-en-3-one epoxide: A versatile intermediate for the synthesis of cyclopentyl carbocyclic 2-deoxy-, 3-deoxy- &amp; ara- ribonucleoside analogues
  作者：Belén M Domínguez、Paul M Cullis

  DOI：10.1016/s0040-4039(99)01113-2

  日期：1999.7

  5,6-Epoxy-exo-2-azabicyclo[2.2.1]heptan-3-one has been used as a versatile intermediate in the synthesis of 2-deoxy-, 3-deoxy- and ara- cyclopentyl carbocyclic nucleosides. An efficient, short synthesis of the (+) carbocyclic thymidine 13 is reported.

  5，6-环氧-外-2--2-氮杂双环[2.2.1]庚-3-已被用作合成2-脱氧，3-脱氧和芳基-环戊基碳环核苷的通用中间体。报道了（+）碳环胸苷13的有效的，短的合成。
• Legraverend, Michel; Bisagni, Emile; Huel, Christiane, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1881
  作者：Legraverend, Michel、Bisagni, Emile、Huel, Christiane

  DOI：——

  日期：——
• Synthesis and Fungistatic Activity of Bicyclic Lactones and Lactams against <i>Botrytis cinerea</i>, <i>Penicillium citrinum</i>, and <i>Aspergillus glaucus</i>
  作者：Paulina Walczak、Jakub Pannek、Filip Boratyński、Agata Janik-Polanowicz、Teresa Olejniczak

  DOI：10.1021/jf502148h

  日期：2014.8.27

  Six analogues of natural trans-4-butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and three derivatives, 11, 12, and 13, of Vince lactam (10) were synthesized and tested as fungistatic agents against Botrytis cinerea AM235, Penicillium citrinum AM354, and six strains of Aspergillus. Moreover, bioresolution carried out by means of whole cell microorganisms and commercially available enzymes afforded opposite enantiomerically enriched (-) and (+) isomers of Vince lactam (10), respectively. The effect of compound structures and stereogenic centers on biological activity has been discussed. The highest fungistatic activity was observed for four lactones: 3, 4, 7, and 8 (IC50 = 104.6-115.2 μg/mL) toward B. cinerea AM235. cis-5,6-Epoxy-2-aza[2.2.1]heptan-3-one (13) indicated significant fungistatic activity (IC50 = 107.1 μg/mL) against Aspergillus glaucus AM211. trans-4-Butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and trans-4-butyl-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (7) exhibited high fungistatic activity (IC50 = 143.2 and 110.2 μg/mL, respectively) against P. citrinum AM354 as well.
• Preparation of 2’,3’-Oxirane-fused Carbocyclic Nucleosides Based on N-Substituted 2-Azabicyclo[2.2.1]hept-5-en-3-ones
  作者：Minoru Ishikura、Kota Matsumoto、Atsushi Murakami

  DOI：10.3987/com-04-s(p)19

  日期：——

  The epoxidation of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-ones (1) led to the exo-selective formation of epoxides (2), and the use of 2 for the preparation of 2',3'-oxirane-fused carbocyclic nucleosides (10) was attempted.