(1RS,5SR,6SR)-5-bromo-7-oxabicyclo<4.3.0>nonan-8-one | 56764-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (1RS,5SR,6SR)-5-bromo-7-oxabicyclo<4.3.0>nonan-8-one
• 英文别名: trans-9-bromo-cis-2-oxabicyclo[4.3.0]nonan-3-one；(±)-7-bromohexahydrobenzofuran-2(3H)-one；(3aR,7S,7aS)-7-bromo-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one
• CAS: 56764-24-0；76837-84-8；85297-50-3
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: CPJOVXXSCQIBMX-CHKWXVPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1RS,5SR,6SR)-5-bromo-7-oxabicyclo<4.3.0>nonan-8-one 在 sodium methylate 作用下， 反应 1.0h， 以89%的产率得到Methyl (1S^*,2R^*,3S^*)-2-<3-(1,2-epoxycyclohexanyl)>acetate
  参考文献：
  名称：

  Miyashita, Kazuyuki; Tanaka, Akira; Mizuno, Hiroaki, Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 847 - 852

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (cyclohexen-3-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以70%的产率得到(1RS,5SR,6SR)-5-bromo-7-oxabicyclo<4.3.0>nonan-8-one
  参考文献：
  名称：

  Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones

  摘要：

  Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo-[4.3.0]nonan-2-one (3c), IC50 = 30.1 mu g/mL (0.10 mu M/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC50 = 72.2 mu g/mL (0.47 mu M/mL), toward F. oxysporum AM 13.

  DOI：

  10.1021/jf105019u

文献信息

• Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics
  作者：Haripriyo Mondal、Md Raja Sk、Modhu Sudan Maji

  DOI：10.1039/d0cc04673f

  日期：——

  Alkoxyamide has been reported as a catalyst for the activation of N-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery

  据报道，烷氧基酰胺是一种催化剂，用于在亲脂性溶剂中活化N-溴琥珀酰亚胺来进行溴化和各种底物的溴化反应，并观察到对本底反应的充分抑制。活性位点的关键特征是连接至磺酰胺部分的烷氧基，这有助于将溴物种从溴源接收到基质以及从基质向基质的传递。
• Oxidative oxygen-nucleophilic bromo-cyclization of alkenyl carbonyl compounds without organic wastes using alkali metal reagents in green solvent
  作者：Katsuhiko Moriyama、Chihiro Nishinohara、Toru Sugiue、Hideo Togo

  DOI：10.1039/c5ra19851h

  日期：——

  developed via the oxidative umpolung of bromide using alkali metal bromide and inorganic oxidant to provide the corresponding cyclization products in high yields. In particular, the use of AcOEt, the solvent of choice for green sustainable reactions, led to the high reactivities of the present reactions. This methodology is highly recommended for green sustainable chemistry because it uses stable and non-hazardous

  通过使用碱金属溴化物和无机氧化剂，通过溴化物的氧化反应，开发了烯基羧酸的溴内酯化和作为氧亲核性溴环化反应的N-烯丙基酰胺的溴环化反应，从而高收率地提供了相应的环化产物。特别地，使用AcOEt，绿色可持续反应的首选溶剂，导致了本反应的高反应性。强烈建议将此方法用于绿色可持续化学，因为它使用稳定且无害的试剂代替其他溴试剂和氧化剂，并且不会产生污染环境的有机废物。
• A Convenient Method for Bromolactonization
  作者：Richard C. Cambie、Peter S. Rutledge、Robyn F. Somerville、Paul D. Woodgate

  DOI：10.1055/s-1988-27790

  日期：——

  Bromolactones are conveniently obtained from unsaturated acids, bromine, and thallium(I) carbonate.

  溴内酯可以方便地从不饱和酸、溴和碳酸铊(I)中获得。
• Novel Bromolactonization Using a Dimethyl Sulfoxide-Trimethylsilyl Bromide-Amine System; Unusual cis-Addition of trans-6-Substituted 3-Cyclohexene-1-carboxylic Acids
  作者：Chuzo Iwata、Akira Tanaka、Hiroaki Minuzo、Kazuyki Miyashita

  DOI：10.3987/com-90-5374

  日期：——
• Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones
  作者：Teresa Olejniczak、Filip Boratyński、Agata Białońska

  DOI：10.1021/jf105019u

  日期：2011.6.8

  Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo-[4.3.0]nonan-2-one (3c), IC50 = 30.1 mu g/mL (0.10 mu M/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC50 = 72.2 mu g/mL (0.47 mu M/mL), toward F. oxysporum AM 13.