(5R,10S)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate | 876301-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (5R,10S)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate
• 英文别名: verongidoic acid methyl ester；methyl (5R,6S)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxylate
• CAS: 876301-52-9
• 化学式: C₁₁H₁₁Br₂NO₅
• 分子量: 397.02
• InChiKey: BWARHGMOCWYQHN-KOLCDFICSA-N

物化性质

• 沸点：
  478.4±55.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R,10S)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate 在 邻苯二甲酸二甲酯 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(5R)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-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
• 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 吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (5R,10S)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-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

• Synthesis and assignment of the absolute stereochemistry of (+)-hemifistularin 3
  作者：Hironori Kubo、Kaori Matsui、Tsuyoshi Saitoh、Shigeru Nishiyama

  DOI：10.1016/j.tet.2014.07.049

  日期：2014.9

  the marine natural product (+)-hemifistularin 3 in enantiomerically pure form was accomplished by using the amide forming reaction of (+)-spiroisoxazoline ester with the (+)-octopamine derivative. The stereodivergent strategy employed in this effort enabled the assignment of the absolute configurations at the three stereogenic centers in (+)-hemifistularin 3.

  对映体纯形式的海洋天然产物（+）-hemististularin 3的第一个全合成是通过使用（+）-螺杂恶唑啉酯与（+）-章鱼胺衍生物的酰胺形成反应完成的。在这项工作中采用的立体发散策略使得能够在（+）-hemifistularin 3的三个立体发生中心分配绝对构型。
• Total syntheses of subereamollines A and B
  作者：James W. Shearman、Rebecca M. Myers、James D. Brenton、Steven V. Ley

  DOI：10.1039/c0ob00636j

  日期：——

  The first total syntheses of (+)- and (−)-subereamollines A and B are reported. The enantiomeric forms of the natural products were obtained by preparative chiral HPLC separation of the corresponding racemates.

  首次报道了(+)-和(−)-subereamollines A和B的完整合成。这些天然产物的对映体形式通过相应外消旋体的制备性手性高效液相色谱分离获得。
• Asymmetric Oxidative Cyclization of <i>o</i>-Phenolic Oxime-Esters:  First Synthesis of Enantiomerically Enriched Spiroisoxazoline Methyl Esters
  作者：Masatoshi Murakata、Masafumi Tamura、Osamu Hoshino

  DOI：10.1021/jo970082i

  日期：1997.6.1

  A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oxime-ester 1c using a novel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was

  已经描述了一种合成对映体富集的环己二酮螺异恶唑啉（-）-2a的新方法。使用新型旋光性叔醇（-）-3作为手性助剂，对邻苯酚肟酯1c的不对称分子内氧化环化反应顺利进行，从而以83％的收率得到环己二酮螺异异唑啉2c。通过光学拆分，由外消旋（1S，8R，9R，10R）-8-苯基-1-癸醇（4）合成了具有活性的叔醇（-）-3。用CF（3）COOH除去2c中的手性助剂，然后进行甲基化，得到具有S-构型的74％ee（化学收率71％）的甲酯（-）-2a。2awas的绝对构型由海洋天然产物（+）-aeroothionin的合成决定。
• 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.