(-)-calafianin | 881737-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-calafianin
• 英文别名: (1'R,5R,6'S)-4'-bromo-N-[4-[[(1'R,5R,6'S)-4'-bromo-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carbonyl]amino]butyl]-5'-oxospiro[4H-1,2-oxazole-5,2'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxamide
• CAS: 881737-05-9
• 化学式: C₂₂H₂₀Br₂N₄O₈
• 分子量: 628.231
• InChiKey: OPMAEHVWCSXSKG-YMDUPTGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (-)-calafianin 在 magnesium bromide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以83%的产率得到(5R,6S,7S)-7,9-dibromo-N-[4-[[(5R,6S,7S)-7,9-dibromo-6-hydroxy-8-oxo-1-oxa-2-azaspiro[4.5]deca-2,9-diene-3-carbonyl]amino]butyl]-6-hydroxy-8-oxo-1-oxa-2-azaspiro[4.5]deca-2,9-diene-3-carboxamide
  参考文献：
  名称：

  螺异恶唑啉天然产物（+）-卡拉芬宁的全合成和立体化学分配。

  摘要：

  已报道使用不对称亲核环氧化和一氧化氮环加成作为关键步骤合成螺异异唑啉天然产物（+）-卡拉夫宁。所有卡拉芬宁立体异构体的合成和光谱分析导致相对和绝对立体化学的明确分配。

  DOI：

  10.1021/ol053115m
• 作为产物：
  描述：

  在 2-羟基吡啶 、 氢氟酸 、 zinc trifluoromethanesulfonate 、 zirconium(IV) tert-butoxide 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 (-)-calafianin
  参考文献：
  名称：

  螺异恶唑啉天然产物（+）-卡拉芬宁的全合成和立体化学分配。

  摘要：

  已报道使用不对称亲核环氧化和一氧化氮环加成作为关键步骤合成螺异异唑啉天然产物（+）-卡拉夫宁。所有卡拉芬宁立体异构体的合成和光谱分析导致相对和绝对立体化学的明确分配。

  DOI：

  10.1021/ol053115m

文献信息

• 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。
• 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 and Stereochemical Assignment of the Spiroisoxazoline Natural Product (+)-Calafianin¹
  作者：Sujata Bardhan、Daniel C. Schmitt、John A. Porco

  DOI：10.1021/ol053115m

  日期：2006.3.2

  Synthesis of the spiroisoxazoline natural product (+)-calafianin is reported using asymmetric nucleophilic epoxidation and nitrile oxide cycloaddition as key steps. Synthesis and spectral analysis of all calafianin stereoisomers led to unambiguous assignment of relative and absolute stereochemistry.

  已报道使用不对称亲核环氧化和一氧化氮环加成作为关键步骤合成螺异异唑啉天然产物（+）-卡拉夫宁。所有卡拉芬宁立体异构体的合成和光谱分析导致相对和绝对立体化学的明确分配。