13-formyl-1,11-dioxa[11]paracyclophane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 13-formyl-1,11-dioxa[11]paracyclophane
• 英文别名: 2,12-Dioxabicyclo[11.2.2]heptadeca-1(15),13,16-triene-14-carbaldehyde；2,12-dioxabicyclo[11.2.2]heptadeca-1(15),13,16-triene-14-carbaldehyde
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: JIOMBTWOHWHALW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-formyl-1,11-dioxa[11]paracyclophane 在 正丁基锂 、 四甲基乙二胺 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 (S_a)-N-benzyl-N-(1,11-dioxa[11]paracyclophan-13-ylmethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
  参考文献：
  名称：

  Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands

  摘要：

  A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.015
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1,11-二氧[11]对环芳烷 在 仲丁基锂 、 鹰爪豆碱 、 水 、 氯化铵 作用下， 以 乙醚 、 正己烷 、 环己烷 为溶剂， 以70%的产率得到13-formyl-1,11-dioxa[11]paracyclophane
  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 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.
• Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands
  作者：Madhurima Hazra、Kyalo Stephen Kanyiva、Takanori Shibata

  DOI：10.1016/j.tetasy.2016.08.015

  日期：2016.11

  A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained. (C) 2016 Elsevier Ltd. All rights reserved.