4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-12-hydroxy-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate | 1021358-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-12-hydroxy-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate
• CAS: 1021358-78-0
• 化学式: C₂₆H₃₂N₂O₈S
• 分子量: 532.615
• InChiKey: HWAPMAVSSGJOHK-GUSAQODQSA-N

物化性质

• 沸点：
  662.1±65.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-12-hydroxy-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-14-(4-methylphenyl)sulfonyl-12-(4-nitrobenzoyl)oxy-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate
  参考文献：
  名称：

  Expedient Synthesis of the Tetracyclic Core of ent-Nakadomarin A

  摘要：

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.

  DOI：

  10.1021/ol800579j
• 作为产物：
  描述：

  4-O-tert-butyl 3-O-methyl (1S,3S,5S)-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8,11-triene-3,4-dicarboxylate 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 甲苯 、 水 为溶剂， 反应 1.0h， 以71%的产率得到4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-12-hydroxy-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate
  参考文献：
  名称：

  Expedient Synthesis of the Tetracyclic Core of ent-Nakadomarin A

  摘要：

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.

  DOI：

  10.1021/ol800579j

文献信息

• Expedient Synthesis of the Tetracyclic Core of <i>ent</i>-Nakadomarin A
  作者：Haibing Deng、Xiaobao Yang、Zhaolong Tong、Zhong Li、Hongbin Zhai

  DOI：10.1021/ol800579j

  日期：2008.5.1

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.