1,11-dioxa[11](1,4)naphthalenophane | 1221497-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,11-dioxa[11](1,4)naphthalenophane
• 英文别名: 2,12-Dioxatricyclo[11.6.2.014,19]henicosa-1(20),13(21),14,16,18-pentaene
• CAS: 1221497-24-0
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: CRRSKMFHUCBREA-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  436.8±15.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1,11-dioxa[11](1,4)naphthalenophane 在 仲丁基锂 、 鹰爪豆碱 、 碘 作用下， 以 乙醚 、 正己烷 、 环己烷 为溶剂， 以95%的产率得到(Rp)-13-iodo-1,11-dioxa[11](1,4)naphthalenophane
  参考文献：
  名称：

  Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophanes via Catalytic Asymmetric ortho-Lithiation

  摘要：

  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.

  DOI：

  10.1021/ol100444u
• 作为产物：
  描述：

  1,4-二羟基萘 、 1,9-二溴壬烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以48%的产率得到1,11-dioxa[11](1,4)naphthalenophane
  参考文献：
  名称：

  Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophanes via Catalytic Asymmetric ortho-Lithiation

  摘要：

  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.

  DOI：

  10.1021/ol100444u

文献信息

• Enantioselective Synthesis of Planar-Chiral Phosphines with 1,N-Dioxa[N]paracyclophane Scaffold and Their Application as Chiral Ligands
  作者：Takanori Shibata、Kazumasa Kanda、Shoya Oshima、Tsubasa Shizuno、Risa Hamanaka、Miku Fukai

  DOI：10.3987/com-13-s(s)105

  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.
• 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.