4-Methoxy-2-(acetylamino)fluorene | 138235-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-Methoxy-2-(acetylamino)fluorene
• 英文别名: N-2-<4-Methoxy-fluorenyl>-acetamid；N-(4-methoxy-9H-fluoren-2-yl)acetamide
• CAS: 138235-72-0
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KFOYXNFIJFJOFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 4-Hydroxy-2-(acetylamino)fluorene 生成 4-Methoxy-2-(acetylamino)fluorene
  参考文献：
  名称：

  Nucleophilic substitution on the ultimate hepatacarcinogen N-(sulfonatooxy)-2-(acetylamino)fluorene by aromatic amines

  摘要：

  The kinetics and products of the reactions of the title compound 1 with aniline (5) and N,N-dimethylaniline (6) were investigated in MeOH. Addition of 5 (0.1-0.4 M) to a solution of 1 in MeOD-d4 has no effect on the overall rate of decomposition of 1 but generates a number of adducts (20-24) in moderate to high yield. The yields of all solvolysis products, except the rearranged O-sulfates 18 and 19, are suppressed by the addition of 5. The kinetic and product data are consistent with an S(N)1 mechanism (Scheme IV) in which 18 and 19 are generated by internal return from a tight ion pair, but all other products are generated by nucleophilic attack on a free nitrenium ion or solvent separated ion pair. The reaction of 6 with 1 shows similar characteristics to that of 5 with the exception that 6 reduces 1 in moderate yield to generate 2-(acetylamino)fluorene (25). This reduction occurs in competition with reaction to generate adducts (26, 27) similar to those obtained with 5. Kinetic and product data indicate that 25 is generated by reaction of 6 with a nitrenium ion intermediate. The differences in the behavior of 5 and 6 may be explained by cyclic voltammetry results which show that 6 is oxidized in MeOH more readily than 5 by about 2.5 kcal/mol. The reaction of 1 with 5 and 6 is considerably different from the reactions of the same amines with the N-aryl-O-pivaloylhydroxylamines, which were previously shown to proceed via an S(N)2 mechanism. This change in mechanism may be attributed, in part, to increased steric hindrance at the nitrogen of 1 due to the N-acetyl group.

  DOI：

  10.1021/jo00030a043

文献信息

• Novak Michael, Rangappa Kanchugarakoppal, Manitsas Rebecca K., J. Org. Chem, 58 (1993) N 27, S 7813- 7821
  作者：Novak Michael, Rangappa Kanchugarakoppal, Manitsas Rebecca K.

  DOI：——

  日期：——