dimethyl 4,5,10,11-tetrahydro-5,10-[1,2]benzenobenzo[6,7]cyclonona[1,2,3-de]naphthalene-5,10-dicarboxylate | 1449140-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: dimethyl 4,5,10,11-tetrahydro-5,10-[1,2]benzenobenzo[6,7]cyclonona[1,2,3-de]naphthalene-5,10-dicarboxylate
• 英文别名: Dimethyl hexacyclo[11.6.6.13,7.014,19.020,25.011,26]hexacosa-3,5,7(26),8,10,14,16,18,20,22,24-undecaene-1,13-dicarboxylate；dimethyl hexacyclo[11.6.6.13,7.014,19.020,25.011,26]hexacosa-3,5,7(26),8,10,14,16,18,20,22,24-undecaene-1,13-dicarboxylate
• CAS: 1449140-57-1
• 化学式: C₃₀H₂₄O₄
• 分子量: 448.518
• InChiKey: UBEALQBQSARSHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,8-双(溴甲基)萘 、 二甲基蒽-9,10-二羧酸酯 在 萘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 以61%的产率得到dimethyl 4,5,10,11-tetrahydro-5,10-[1,2]benzenobenzo[6,7]cyclonona[1,2,3-de]naphthalene-5,10-dicarboxylate
  参考文献：
  名称：

  A One-Step, Versatile Synthesis of Dibenzo [n.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction

  摘要：

  A series of dibenzo [n.2.2] bicyclic compounds (n = 2-20) were prepared in one step and good yields starting from dimethyl anthracene-9, 10-dicarboxylate. Reduction of the aromatic diester using lithium/naphthalene led to a bis-enolate that was cyclized with a variety of bis-electrophiles. The ease of the cyclization is probably due to the puckered conformation of the intermediate formed after the first alkylation step, in which the newly introduced chain that will become the bridge portion occupies a pseudoaxial position, positioning the leaving group close to the enolate nucleophile in the macrocyclization step.

  DOI：

  10.1021/ol4016767

文献信息

• A One-Step, Versatile Synthesis of Dibenzo [<i>n</i>.2.2] Macrobicyclic Compounds via a Conformation-Directed Macrocyclization Reaction
  作者：Rubén Lobato、Alberte X. Veiga、Jaime Pérez-Vázquez、Fernando Fernández-Nieto、M. Rita Paleo、F. Javier Sardina

  DOI：10.1021/ol4016767

  日期：2013.8.16

  A series of dibenzo [n.2.2] bicyclic compounds (n = 2-20) were prepared in one step and good yields starting from dimethyl anthracene-9, 10-dicarboxylate. Reduction of the aromatic diester using lithium/naphthalene led to a bis-enolate that was cyclized with a variety of bis-electrophiles. The ease of the cyclization is probably due to the puckered conformation of the intermediate formed after the first alkylation step, in which the newly introduced chain that will become the bridge portion occupies a pseudoaxial position, positioning the leaving group close to the enolate nucleophile in the macrocyclization step.