methyl (1'S,5S,6'R)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxylate | 294208-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1'S,5S,6'R)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxylate
• CAS: 294208-16-5
• 化学式: C₁₀H₈BrNO₅
• 分子量: 302.081
• InChiKey: IBLHUGWCIJHLQX-OYNCUSHFSA-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：

  四亚甲基二胺 、 methyl (1'S,5S,6'R)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxylate 生成 (+)-calafianin
  参考文献：
  名称：

  Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.11.097
• 作为产物：
  描述：

  (5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以59%的产率得到methyl (1'S,5S,6'R)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.11.097

文献信息

• Enantioselective Preparation and Enzymatic Cleavage of Spiroisoxazoline Amides
  作者：Kim Goldenstein、Thomas Fendert、Peter Proksch、Ekkehard Winterfeldt

  DOI：10.1016/s0040-4020(00)00342-2

  日期：2000.6

  Several enantiopure spiroisoxazoline amides were prepared from tert-butylester 22, which is obtained via an enantiotopic groups differentiating high pressure Diels–Alder cycloaddition. Treatment of these amides with an isoxazoline-splitting enzyme, which is involved in an injury induced defense reaction of the sponge Aplysina cauliformis, proves the bromoatoms in the cyclohexenone moiety to be important

  从叔丁基酯22制备了几种对映体纯的螺异异唑啉酰胺，它们是通过区分高压Diels-Alder环加成反应的对映体基团获得的。用异恶唑啉分解酶处理这些酰胺，参与海绵诱导的海绵状Aplysina的损伤诱导防御反应，证明环己烯酮部分中的溴原子对酶结合很重要，而N-H键的存在结果证明，单烷基酰胺对于环裂是必不可少的。讨论了这些结果与环分裂机理的相关性。
• 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.