(+/-)-methyl (1S,2S,6R)-4-bromo-5-oxo-7-oxaspiro[bicyclo[4.1.0]hept-3-ene-2,5'(4'H)isoxazole]-3'-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-methyl (1S,2S,6R)-4-bromo-5-oxo-7-oxaspiro[bicyclo[4.1.0]hept-3-ene-2,5'(4'H)isoxazole]-3'-carboxylate
• 英文别名: methyl (1'R,5R,6'S)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxylate
• 化学式: C₁₀H₈BrNO₅
• 分子量: 302.081
• InChiKey: IBLHUGWCIJHLQX-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl (1S,2S,6R)-4-bromo-5-oxo-7-oxaspiro[bicyclo[4.1.0]hept-3-ene-2,5'(4'H)isoxazole]-3'-carboxylate 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以100%的产率得到
  参考文献：
  名称：

  Total Synthesis, Structural Revision, and Biological Evaluation of Calafianin, a Marine Spiroisoxazoline from the Sponge,Aplysina gerardogreeni

  摘要：

  报道的自然卡拉法宁（1）及其异构体在环氧区域13通过顺式和反式螺异噁唑啉化合物成功合成，这些化合物是通过对羟亚氨基苯酚衍生物7的电化学氧化产物，再经过Zn[BH4]2还原得到的。合成的（±）-1和（±）-13的光谱数据比较导致了对自然卡拉法宁结构的修订，确认其为13，具有环氧和异噁唑啉氧之间的反式关系。此外，还讨论了1和13之间抗菌活性显著差异。

  DOI：

  10.1246/bcsj.79.134
• 作为产物：
  描述：

  (5R,10S)-7,9-Dibromo-10-hydroxy-8-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6-diene-3-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以165 mg的产率得到(+/-)-methyl (1S,2S,6R)-4-bromo-5-oxo-7-oxaspiro[bicyclo[4.1.0]hept-3-ene-2,5'(4'H)isoxazole]-3'-carboxylate
  参考文献：
  名称：

  Total Synthesis, Structural Revision, and Biological Evaluation of Calafianin, a Marine Spiroisoxazoline from the Sponge,Aplysina gerardogreeni

  摘要：

  报道的自然卡拉法宁（1）及其异构体在环氧区域13通过顺式和反式螺异噁唑啉化合物成功合成，这些化合物是通过对羟亚氨基苯酚衍生物7的电化学氧化产物，再经过Zn[BH4]2还原得到的。合成的（±）-1和（±）-13的光谱数据比较导致了对自然卡拉法宁结构的修订，确认其为13，具有环氧和异噁唑啉氧之间的反式关系。此外，还讨论了1和13之间抗菌活性显著差异。

  DOI：

  10.1246/bcsj.79.134

文献信息

• Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative
  作者：Takahisa Ogamino、Rika Obata、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2005.11.097

  日期：2006.1

  Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and structural revision of calafianin, a member of the spiroisoxazole family isolated from the marine sponge, Aplysina gerardogreeni
  作者：Takahisa Ogamino、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2004.12.084

  日期：2005.2

  Calafianin I was successfully synthesized by employing a spiroisoxazoline compound, which was produced by electrochemical oxidation of the oximino-phenol derivative 7 followed by reduction. This investigation revealed a structural revision of 1, the trans-relationship of two oxygen atoms between the epoxide and the isoxazoline. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis, Structural Revision, and Biological Evaluation of Calafianin, a Marine Spiroisoxazoline from the Sponge,<i>Aplysina gerardogreeni</i>
  作者：Takahisa Ogamino、Rika Obata、Hiroshi Tomoda、Shigeru Nishiyama

  DOI：10.1246/bcsj.79.134

  日期：2006.1

  The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH4]2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.

  报道的自然卡拉法宁（1）及其异构体在环氧区域13通过顺式和反式螺异噁唑啉化合物成功合成，这些化合物是通过对羟亚氨基苯酚衍生物7的电化学氧化产物，再经过Zn[BH4]2还原得到的。合成的（±）-1和（±）-13的光谱数据比较导致了对自然卡拉法宁结构的修订，确认其为13，具有环氧和异噁唑啉氧之间的反式关系。此外，还讨论了1和13之间抗菌活性显著差异。