3-Methoxy-2-(acetylamino)fluorene | 6893-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-Methoxy-2-(acetylamino)fluorene
• 英文别名: N-(3-Methoxy-2-fluorenyl)acetamide；N-(3-methoxy-fluoren-2-yl)-acetamide；N-(3-Methoxy-fluoren-2-yl)-acetamid；N-(3-methoxy-9H-fluoren-2-yl)acetamide
• CAS: 6893-21-6
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: UTZPUKWFYZKODS-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：

  3-methoxy-9H-fluorene 在 吡啶 、 硝酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 3-Methoxy-2-(acetylamino)fluorene
  参考文献：
  名称：

  致癌物的Omicron-甲氧基衍生物N-2-芴基乙酰胺。潜在的潜在生物芳构剂。

  摘要：

  DOI：

  10.1021/jm00323a018

文献信息

• Nucleophilic aromatic substitution on ester derivatives of carcinogenic N-arylhydroxamic acids by aniline and N,N-dimethylaniline
  作者：Michael Novak、Kanchugarakoppal S. Rangappa、Rebecca K. Manitsas

  DOI：10.1021/jo00079a028

  日期：1993.12

  Decomposition of N-(pivaloyloxy)-2-(acetylamino)fluorene (1b) and N-(sulfonatooxy)-4-(acetylamino)-biphenyl (2a) in MeOH occurs predominately via N-0 bond cleavage to yield oxazoles (5, 6, 23), methoxy adducts (7,8,24,25,26), and rearrangement products (10b,11b,28). Minor ester methanolysis paths lead to the N-arylhydroxamic acids (9, 27). In the presence of 0.1 M aniline (3), 1b yields a number of adducts (14-18) identical to those previously obtained from the reaction of 3 with N-(sulfonatooxy)-2-(acetylamino)fluorene (1a). This occurs with no change in the rate constant for decomposition of 1b. At 0.1 M 3 all solvolysis products of 1b, except the rearrangement products 10 band 11b, are reduced below detectable levels. Similar results were obtained for 2a, which yields the adducts 30-35 in the presence of 3 and 36-38 in the presence of N,N-dimethylaniline (4). These results are consistent with a mechanism (Scheme V) in which the N-O bond heterolysis leads to a tight ion pair that can undergo internal return to yield the rearrangement products or diffusional separation to yield the free ion. The free nitrenium ion can be trapped by solvent or added nucleophiles. Both the N-acetyl-N-(4-biphenylyl)nitrenium ion (45) and the N-acetyl-N-(2-fluorenyl)nitrenium ion (48) react slowly enough with the solvent to undergo selective reaction with strong nucleophiles. Since 1a, 1b, and 2a span the reactivity range of the ester derivatives of the common N-arylhydroxamic acids which undergo N-O bond heterolysis in H2O, it appears that all of the carcinogenic esters will react with simple aromatic amines via an S(N)1 mechanism.
• 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：——
• o-Methoxy Derivatives of the Carcinogen, N-2-Fluorenylacetamide. Potential Latent Biological Arylating Agents¹
  作者：H. T. Nagasawa、H. R. Gutmann

  DOI：10.1021/jm00323a018

  日期：1966.9