Dioxa<12>paracyclophane | 6786-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dioxa<12>paracyclophane
• 英文别名: 1,12-dioxa[12]paracyclophane；1,12-dioxa-[12]paracyclophane；1,12-Dioxa-[12]paracyclophan；2,13-Dioxabicyclo[12.2.2]octadeca-1(16),14,17-triene
• CAS: 6786-22-7
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: JOTQDDHPFAOPPH-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C
• 沸点：
  120-125 °C
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dioxa<12>paracyclophane 在 乙醚 、 苯基锂 作用下， 生成 1,12-dioxa-[12]paracyclophane-14-carboxylic acid
  参考文献：
  名称：

  Luettringhaus; Gralheer, Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 112,118

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(10-bromo-decyloxy)-phenol 在 异戊醇 、 potassium carbonate 作用下， 生成 Dioxa<12>paracyclophane
  参考文献：
  名称：

  Luettringhaus, Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 181,203

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Planar-Chiral 1,<i>n</i>-Dioxa[<i>n</i>]paracyclophanes via Catalytic Asymmetric <i>ortho</i>-Lithiation
  作者：Kazumasa Kanda、Kohei Endo、Takanori Shibata

  DOI：10.1021/ol100444u

  日期：2010.5.7

  Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of see-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.
• Hochmuth, Detlev H.; Koenig, Wilfried A., Liebigs Annalen, 1996, # 6, p. 947 - 951
  作者：Hochmuth, Detlev H.、Koenig, Wilfried A.

  DOI：——

  日期：——
• Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophane derivatives for the generation of planar chirality
  作者：Kazumasa Kanda、Risa Hamanaka、Kohei Endo、Takanori Shibata

  DOI：10.1016/j.tet.2011.12.031

  日期：2012.2

  The asymmetric induction of planar chirality in 1,n-dioxa[n]paracyclophane derivatives via asymmetric ortho-lithiation is described. Enantioselective ortho-lithiation of unflippable 1,n-dioxa[n]paracyclophanes (n <= 11) using sec-BuLi-(-)-sparteine at -78 degrees C and subsequent treatment with electrophiles gave the corresponding planar-chiral monosubstituted paracyclophanes with excellent ee. Further lithiation of these compounds and treatment with electrophiles gave planar-chiral paracyclophanes with two different substituents. Dilithiation of unflippable 1,n-dioxa[n]paracyclophanes gave the corresponding C(2)symmetrical disubstituted products with almost perfect ee. In the case of flippable 1,n-dioxa[n]paracyclophanes (n >= 12), a stepwise reaction was required for the highly enantioselective formation of disubstituted products. (C) 2011 Elsevier Ltd. All rights reserved.
• Ring-closure reactions. 17. The kinetics of formation of meta- and paracyclophane diethers
  作者：Antonella Dalla Cort、Luigi Mandolini、Bernardo Masci

  DOI：10.1021/jo01307a043

  日期：1980.9
• Luettringhaus, Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 181,203
  作者：Luettringhaus

  DOI：——

  日期：——