21-Iodo-2,13-dioxatricyclo[12.6.2.015,20]docosa-1(21),14(22),15,17,19-pentaene | 1356391-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 21-Iodo-2,13-dioxatricyclo[12.6.2.015,20]docosa-1(21),14(22),15,17,19-pentaene
• CAS: 1356391-25-7
• 化学式: C₂₀H₂₅IO₂
• 分子量: 424.322
• InChiKey: UYTBTPBGWVFWNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,12-dioxa[12](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82%的产率得到21-Iodo-2,13-dioxatricyclo[12.6.2.015,20]docosa-1(21),14(22),15,17,19-pentaene
  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

• 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.