13,15-Diiodo-2,11-dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene | 1357020-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 13,15-Diiodo-2,11-dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene
• CAS: 1357020-22-4
• 化学式: C₁₄H₁₈I₂O₂
• 分子量: 472.105
• InChiKey: GVBOCELMBIEEGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,10-dioxa[10]paracyclophane 在 仲丁基锂 、 鹰爪豆碱 、 碘 作用下， 以 乙醚 为溶剂， 反应 14.0h， 以91%的产率得到13,15-Diiodo-2,11-dioxabicyclo[10.2.2]hexadeca-1(14),12,15-triene
  参考文献：
  名称：

  Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophane derivatives for the generation of planar chirality

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.12.031

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.