methyl 2'-hydroxymethyl-4',6'-dimethoxy-2-nitro-[1,1'-biphenyl]-3-carboxylate | 1166398-75-9

• 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: methyl 2'-hydroxymethyl-4',6'-dimethoxy-2-nitro-[1,1'-biphenyl]-3-carboxylate
• CAS: 1166398-75-9
• 化学式: C₁₇H₁₇NO₇
• 分子量: 347.324
• InChiKey: VPFFSLUVPBMDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2'-hydroxymethyl-4',6'-dimethoxy-2-nitro-[1,1'-biphenyl]-3-carboxylate 、 甲基磺酰氯 在 水 、 氯化铵 、 锌 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 7-(2-methanesulfonyloxymethyl-4,6-dimethoxyphenyl)-2,1-benzisoxazol-3(1H)-one
  参考文献：
  名称：

  Synthesis of the Isoxazolo[4,3,2-de]phenanthridinone Moiety of the Parnafungins

  摘要：

  A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl3 and the phenanthridine N-oxide in aqueous base.

  DOI：

  10.1021/ol901054r
• 作为产物：
  描述：

  [2-(hydroxymethyl)-4,6-dimethoxyphenyl]boronic acid 、 2-硝基-3-氯苯甲酸甲酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate tribasic 、 palladium diacetate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 以213 mg的产率得到methyl 2'-hydroxymethyl-4',6'-dimethoxy-2-nitro-[1,1'-biphenyl]-3-carboxylate
  参考文献：
  名称：

  Synthesis of Hexacyclic Parnafungin A and C Models

  摘要：

  A convergent, practical route to unstable hexacyclic parnafungin A and C models has been developed. Two iodoxanthones were prepared in four or five steps (33-50% overall yield). Suzuki-Miyaura coupling of the iodoxanthones with excess readily available 3-carbomethoxy-2-nitrophenyl pinacol boronate afforded the hindered highly functionalized 2-arylxanthones (53-58%) in the first key step. In the second key step, zinc reduction gave benzisoxazolinones that were treated with MsCl and then base to generate the unstable hexacyclic parnafungin A (13% overall yield for 8 steps) and C (8% overall yield for 9 steps) models. Analogously to the parnafungins, hexacyclic parnafungin C model decomposes to a phenanthridine with a half-life of 2 d in CDCI3.

  DOI：

  10.1021/jo101826p