diethyl (3-acetyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate | 1269632-66-7

• 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: diethyl (3-acetyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate
• 英文别名: diethyl-1-phenylsulfonyl-(3-acetyl-indol-2-yl)methylphosphonate
• CAS: 1269632-66-7
• 化学式: C₂₁H₂₄NO₆PS
• 分子量: 449.464
• InChiKey: RESGHCLTCSLYHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91.67
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl (3-acetyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate 、 邻硝基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以40%的产率得到(E)-3-(2-nitrophenyl)-1-(2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Calothrixins and Its Analogs Using FeCl₃-Mediated Domino Reaction Protocol

  摘要：

  A novel one pot synthesis of calothrixin B and its analogs is achieved involving an FeCl3-mediated domino reaction of enamines in dry DMF at reflux. Alternatively, the enamines upon interaction with CuBr2 in DMF at reflux led to the formation of 1-phenylsulfony-2-(2'-nitroaryl)-4-hydroxycarbazole-3-carbaldehydes in excellent yields.

  DOI：

  10.1021/ol4015738
• 作为产物：
  描述：

  3-acetyl-2-methyl-1-(phenylsulfonyl)indole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 zinc dibromide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 diethyl (3-acetyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate
  参考文献：
  名称：

  Synthesis of Calothrixins and Its Analogs Using FeCl₃-Mediated Domino Reaction Protocol

  摘要：

  A novel one pot synthesis of calothrixin B and its analogs is achieved involving an FeCl3-mediated domino reaction of enamines in dry DMF at reflux. Alternatively, the enamines upon interaction with CuBr2 in DMF at reflux led to the formation of 1-phenylsulfony-2-(2'-nitroaryl)-4-hydroxycarbazole-3-carbaldehydes in excellent yields.

  DOI：

  10.1021/ol4015738

文献信息

• Lewis Acid-Mediated Michaelis−Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
  作者：Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Radhakrishnan Sureshbabu、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol1029436

  日期：2011.3.18

  A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.