8-nitro-3'-tosyldiosmetin | 1217077-63-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-nitro-3'-tosyldiosmetin
• 英文别名: [5-(5,7-Dihydroxy-8-nitro-4-oxochromen-2-yl)-2-methoxyphenyl] 4-methylbenzenesulfonate；[5-(5,7-dihydroxy-8-nitro-4-oxochromen-2-yl)-2-methoxyphenyl] 4-methylbenzenesulfonate
• CAS: 1217077-63-8
• 化学式: C₂₃H₁₇NO₁₀S
• 分子量: 499.455
• InChiKey: MCOFNDBULXEZGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  174
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-nitro-3'-tosyldiosmetin 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以75%的产率得到8-nitrodiosmetin
  参考文献：
  名称：

  Unexpected B-ring regioselective di-nitration of diosmetin, a Citrus flavonoid

  摘要：

  Nitration in position C-8 of diosmetin, an easily available citroflavonoid, was studied in order to gain access to original analogs. The one-step nitration proved impossible, as mono or di-nitration on C-2' and C-6' positions on the lateral B ring of the molecule was exclusively observed. This surprisingly straightforward di-nitration of ring B, showing a lack of reactivity of ring A despite its high activation, has never been mentioned to date. Nitration in position C-8 was therefore performed in five steps, requiring selective deactivation of ring B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.062
• 作为产物：
  描述：

  3'-tosyldiosmetin 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.75h， 以45%的产率得到8-nitro-3'-tosyldiosmetin
  参考文献：
  名称：

  Unexpected B-ring regioselective di-nitration of diosmetin, a Citrus flavonoid

  摘要：

  Nitration in position C-8 of diosmetin, an easily available citroflavonoid, was studied in order to gain access to original analogs. The one-step nitration proved impossible, as mono or di-nitration on C-2' and C-6' positions on the lateral B ring of the molecule was exclusively observed. This surprisingly straightforward di-nitration of ring B, showing a lack of reactivity of ring A despite its high activation, has never been mentioned to date. Nitration in position C-8 was therefore performed in five steps, requiring selective deactivation of ring B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.062

文献信息

• Unexpected B-ring regioselective di-nitration of diosmetin, a Citrus flavonoid
  作者：Guy Lewin、Jean-Christophe Jullian、Jordi Rodrigo

  DOI：10.1016/j.tetlet.2009.12.062

  日期：2010.2

  Nitration in position C-8 of diosmetin, an easily available citroflavonoid, was studied in order to gain access to original analogs. The one-step nitration proved impossible, as mono or di-nitration on C-2' and C-6' positions on the lateral B ring of the molecule was exclusively observed. This surprisingly straightforward di-nitration of ring B, showing a lack of reactivity of ring A despite its high activation, has never been mentioned to date. Nitration in position C-8 was therefore performed in five steps, requiring selective deactivation of ring B. (C) 2009 Elsevier Ltd. All rights reserved.