(1R,2R,6R)-3-(2-hydroxybenzamido)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl hexanoate | 1313573-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,6R)-3-(2-hydroxybenzamido)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl hexanoate
• 英文别名: [(1R,2R,6R)-3-[(2-hydroxybenzoyl)amino]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] hexanoate
• CAS: 1313573-75-9
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: GXGBDIRWEHODNW-FGTMMUONSA-N

物化性质

• 沸点：
  583.9±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-epoxy-4-hexanoyloxy-5-[(2-hexanoyloxybenzoyl)amino]cyclohex-5-en-1-one 在 Burkholderia cepacia lipase 、 水 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以69%的产率得到(-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
  参考文献：
  名称：

  Chemoenzymatic synthesis of (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent inhibitor on NF-κB

  摘要：

  A new route for (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent NF-kappa B inhibitor, was established by chemoenzymatic approach. Elaboration on the asymmetric epoxidation of a p-benzoquinone monoketal with benzylcinchonidinium tert-butylhydroperoxide yielded an epoxyenone, in 79.8% ee and 57% yield in reproducible manner. By way of the transformation of this key intermediate to enantiomerically pure (2S,35,4S)-DHMEQ the contaminating undesired enantiomer could be effectively removed by applying Burkholderia cepacia lipase-catalyzed hydrolysis of diacylated precursor. The above integrated combination of chemical asymmetric synthesis and enzyme-catalyzed kinetic resolution enabled us to prepare active DHMEQ in a large-scale. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.013

文献信息

• Chemoenzymatic synthesis of (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent inhibitor on NF-κB
  作者：Manabu Hamada、Yukihiro Niitsu、Chihiro Hiraoka、Ikuko Kozawa、Toshinori Higashi、Mitsuru Shoji、Kazuo Umezawa、Takeshi Sugai

  DOI：10.1016/j.tet.2010.07.013

  日期：2010.8

  A new route for (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent NF-kappa B inhibitor, was established by chemoenzymatic approach. Elaboration on the asymmetric epoxidation of a p-benzoquinone monoketal with benzylcinchonidinium tert-butylhydroperoxide yielded an epoxyenone, in 79.8% ee and 57% yield in reproducible manner. By way of the transformation of this key intermediate to enantiomerically pure (2S,35,4S)-DHMEQ the contaminating undesired enantiomer could be effectively removed by applying Burkholderia cepacia lipase-catalyzed hydrolysis of diacylated precursor. The above integrated combination of chemical asymmetric synthesis and enzyme-catalyzed kinetic resolution enabled us to prepare active DHMEQ in a large-scale. (C) 2010 Elsevier Ltd. All rights reserved.