5-nitro[2.2]paracyclophanepyran-6-one | 872221-35-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-nitro[2.2]paracyclophanepyran-6-one
• 英文别名: 14-Nitro-12-oxatetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,14,17,19-heptaen-13-one；14-nitro-12-oxatetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,14,17,19-heptaen-13-one
• CAS: 872221-35-7
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: FZCNQKZDUDUEFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro[2.2]paracyclophanepyran-6-one 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 22.0~65.0 ℃ 、800.0 MPa 条件下， 反应 43.0h， 生成 5,6-Dimethyl-9-oxapentacyclo[9.8.2.214,17.02,10.03,8]tricosa-1,3(8),4,6,10,14,16,20,22-nonaene
  参考文献：
  名称：

  5-Nitro[2.2]paracyclophanepyran-6-one—building block for the synthesis of [2.2]paracyclophanes containing condensed benzofuran subunits

  摘要：

  The 5-nitro[2.2]paracyclophanepyran-6-one 2 has been synthesized. DBN treatment of the Diels Alder cycloadducts of 2 followed by DDQ oxidation unexpectedly led to [2.2]paracyclophanes containing a condensed benzofuran subunit. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.023
• 作为产物：
  描述：

  硝基乙酸乙酯 、 5-formyl-4-hydroxy[2.2]paracyclophane 在 哌啶 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 23.0h， 以72%的产率得到5-nitro[2.2]paracyclophanepyran-6-one
  参考文献：
  名称：

  5-Nitro[2.2]paracyclophanepyran-6-one—building block for the synthesis of [2.2]paracyclophanes containing condensed benzofuran subunits

  摘要：

  The 5-nitro[2.2]paracyclophanepyran-6-one 2 has been synthesized. DBN treatment of the Diels Alder cycloadducts of 2 followed by DDQ oxidation unexpectedly led to [2.2]paracyclophanes containing a condensed benzofuran subunit. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.023

文献信息

• High pressure and thermal Diels–Alder reactions of 5-nitro[2.2]paracyclophanepyran-6-one
  作者：Lucio Minuti、Assunta Marrocchi、Selvaggia Landi、Mirko Seri、Eszter Gacs-Baitz

  DOI：10.1016/j.tet.2007.04.042

  日期：2007.6

  The Diels-Alder reactions of 5-nitro[2.2] paracyclophanepyran-6-one with 1,3-butadienes and 1,2-dihydro-3-vinyl-naphthalene were examined under thermal and high-pressure conditions. The cycloadditions with 1,3-butadienes occurred in good yield and anti-exo diastereoselectively only under high-pressure conditions; the one with 1,2-dihydro-3-vinyl-naphthalene afforded comparable yields of mixtures of anti/syn adducts under normal and high-pressure conditions. A structural analysis of the reaction products by H-1 and C-13 NMR spectroscopy is presented. (c) 2007 Elsevier Ltd. All rights reserved.