dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate | 68712-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate
• 英文别名: 8-Oxo-5,6,7,8-tetrahydronaphthalin-1,2-dicarbonsaeure-dimethylester；dimethyl 8-oxo-6,7-dihydro-5H-naphthalene-1,2-dicarboxylate
• CAS: 68712-15-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: MSNAVRJFAUSXIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate 在 sodium hydroxide 、 乙酸酐 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 20.25h， 生成 1-[(N-phenylamino)carbonyl]-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Unexpected regiospecific reactivity of a substituted phthalic anhydride

  摘要：

  Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.090
• 作为产物：
  描述：

  5',6'-Dihydrospiro<1,3-dioxolan-2,8'(7'H)naphthalin>-1',2'-dicarbonsaeure-dimethylester 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以51%的产率得到dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate
  参考文献：
  名称：

  Tochtermann, Werner; Koehn, Heinke, Chemische Berichte, 1980, vol. 113, # 10, p. 3249 - 3261

  摘要：

  DOI：

文献信息

• TOCHTERMANN W.; KOEHN H., CHEM. BER., 1980, 113, NO 10, 3249-3261
  作者：TOCHTERMANN W.、 KOEHN H.

  DOI：——

  日期：——
• Unexpected regiospecific reactivity of a substituted phthalic anhydride
  作者：Maria J. Petersson、Camille Marchal、Wendy A. Loughlin、Ian D. Jenkins、Peter C. Healy、Ann Almesåker

  DOI：10.1016/j.tet.2006.11.090

  日期：2007.2

  Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.
• Tochtermann, Werner; Koehn, Heinke, Chemische Berichte, 1980, vol. 113, # 10, p. 3249 - 3261
  作者：Tochtermann, Werner、Koehn, Heinke

  DOI：——

  日期：——