2-(2,4,6-trimethylbenzylidene)-2H-indene-1,3-dione | 54689-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2,4,6-trimethylbenzylidene)-2H-indene-1,3-dione
• 英文别名: 2-[(2,4,6-Trimethylphenyl)methylidene]indene-1,3-dione
• CAS: 54689-97-3
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: LUUDVOUVXRDDEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 C-mesityl-N-methylnitrone 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到2-(2,4,6-trimethylbenzylidene)-2H-indene-1,3-dione
  参考文献：
  名称：

  Solvent-dependent reactivities of acyclic nitrones with β-diketones: catalyst-free syntheses of endiones and enones

  摘要：

  Reactions of the nitrones -O+N(Me)=C(H)Ar 1 (Ar=phenyl 1a, 4-methylphenyl 1b, 2,4,6-trimethylphenyl 1c, and anthracen-9-yl 1d) with the cyclic beta-diketones 1,3-indandione 2 or barbituric acid 3 in CH2Cl2, afford the corresponding endiones 2'a-2'd or 3'a-3'd. In contrast, dimedone 4 reacts with 1a or 1b to give the endione 4'a or 4'b and the bis-adduct 4 '' a or 4 '' h. Nevertheless, reaction of 4 with 1c or 1d in CH2Cl2 furnishes only the endione adducts 4'c or 4'd. However, the reaction of 4 with 1a or 1b in methanol gives only 4 '' a or 4 '' b, respectively. Among acyclic beta-diketones only malonic acid 7 reacts with 1a-1c. Reaction of 7 with 1a in CH2Cl2 forms cinnamic acid 7 '' a, whereas in the case of 1b, the endione 7'b and (E)-3-p-tolylacrylic acid 7 '' b are obtained. The nitrone 1c reacts with 7 in CH2Cl2 to afford the endione 7'c or with acetone yielding (E)-4-mesitylbut-3-en-2-one 8. X-ray analyses are reported for 4'c, 5, and 7 '' b. In addition, the calculated acidity of the hydrogen at the alpha-C atom is shown to correlate with the reactivity of the beta-diketones with nitrones. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.086

文献信息

• Solvent-dependent reactivities of acyclic nitrones with β-diketones: catalyst-free syntheses of endiones and enones
  作者：Jamal Lasri、Grzegorz Gajewski、M. Fátima C. Guedes da Silva、Maxim L. Kuznetsov、Ricardo R. Fernandes、Armando J.L. Pombeiro

  DOI：10.1016/j.tet.2012.06.086

  日期：2012.9

  Reactions of the nitrones -O+N(Me)=C(H)Ar 1 (Ar=phenyl 1a, 4-methylphenyl 1b, 2,4,6-trimethylphenyl 1c, and anthracen-9-yl 1d) with the cyclic beta-diketones 1,3-indandione 2 or barbituric acid 3 in CH2Cl2, afford the corresponding endiones 2'a-2'd or 3'a-3'd. In contrast, dimedone 4 reacts with 1a or 1b to give the endione 4'a or 4'b and the bis-adduct 4 '' a or 4 '' h. Nevertheless, reaction of 4 with 1c or 1d in CH2Cl2 furnishes only the endione adducts 4'c or 4'd. However, the reaction of 4 with 1a or 1b in methanol gives only 4 '' a or 4 '' b, respectively. Among acyclic beta-diketones only malonic acid 7 reacts with 1a-1c. Reaction of 7 with 1a in CH2Cl2 forms cinnamic acid 7 '' a, whereas in the case of 1b, the endione 7'b and (E)-3-p-tolylacrylic acid 7 '' b are obtained. The nitrone 1c reacts with 7 in CH2Cl2 to afford the endione 7'c or with acetone yielding (E)-4-mesitylbut-3-en-2-one 8. X-ray analyses are reported for 4'c, 5, and 7 '' b. In addition, the calculated acidity of the hydrogen at the alpha-C atom is shown to correlate with the reactivity of the beta-diketones with nitrones. (C) 2012 Elsevier Ltd. All rights reserved.