2-(13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)ethanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-(13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)ethanamine
• 化学式: C₂₄H₂₂N₂
• 分子量: 338.452
• InChiKey: LUBSPVCMOFRJMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  白樟油 、 2-(13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)ethanamine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以74%的产率得到(E)-2-{3H-dinaphtho[2,1-c:1',2'-e]azepin-4(5H)-yl}-N-{(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene}ethanamine
  参考文献：
  名称：

  基于冰片基和联萘氮杂手性骨架的新型N,N-配体在钯催化烯丙基取代反应中的合成、配位性质及应用

  摘要：

  这项工作得到了Ministryo dell'Istruzione, dell'Universita e della Ricerca (MIUR), PRIN 2007HMTJWP_005 的支持

  DOI：

  10.1002/ejic.201100113
• 作为产物：
  描述：

  (S)-2,2'-双(溴甲基)-1,1'-联萘 、 乙二胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到2-(13-azapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)ethanamine
  参考文献：
  名称：

  Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions

  摘要：

  Chiral P,N-ligands with pseudo-C-2 and pseudo-C-s symmetry based on chiral pyrrolidine and phospholane rings or on dinaphthatodihydroazepino and dinaphthatodihydrophosphepino moieties were prepared and assessed in the palladium-catalyzed allylic substitutions of allylic acetates. Higher selectivity was achieved with pseudo-C-2-symmetric ligands based on the binaphthyl skeleton than with the analogous C-2-symmetric P,P- and N,N-analogues. Pseudo-C-2-type ligands had properties superior to those of pseudo-meso-type ligands when 1,3-diphenyl-2-propenyl acetate was used as a substrate, whereas the reverse situation was found for 3-cyclohexenyl acetate. Chirally flexible ligands, prepared by substitution of one of the rigid binaphthyl skeletons for a flexible biphenyl system, were found to induce chirality to the same extent as a 1:1 mixture of the rigid ligands.

  DOI：

  10.1021/jo026889e

文献信息

• Influence of Steric Symmetry and Electronic Dissymmetry on the Enantioselectivity in Palladium-Catalyzed Allylic Substitutions
  作者：Jean-Luc Vasse、Robert Stranne、Raivis Zalubovskis、Carole Gayet、Christina Moberg

  DOI：10.1021/jo026889e

  日期：2003.4.1

  Chiral P,N-ligands with pseudo-C-2 and pseudo-C-s symmetry based on chiral pyrrolidine and phospholane rings or on dinaphthatodihydroazepino and dinaphthatodihydrophosphepino moieties were prepared and assessed in the palladium-catalyzed allylic substitutions of allylic acetates. Higher selectivity was achieved with pseudo-C-2-symmetric ligands based on the binaphthyl skeleton than with the analogous C-2-symmetric P,P- and N,N-analogues. Pseudo-C-2-type ligands had properties superior to those of pseudo-meso-type ligands when 1,3-diphenyl-2-propenyl acetate was used as a substrate, whereas the reverse situation was found for 3-cyclohexenyl acetate. Chirally flexible ligands, prepared by substitution of one of the rigid binaphthyl skeletons for a flexible biphenyl system, were found to induce chirality to the same extent as a 1:1 mixture of the rigid ligands.
• Synthesis, Coordination Properties and Application of New <i>N</i> , <i>N</i> ‐Ligands Based on Bornyl and Binaphthylazepine Chiral Backbones in Palladium‐Catalyzed Allylic Substitution Reactions
  作者：Giovanni Bottari、Angelo Meduri、Dario Drommi、Giovanna Brancatelli、Felice Faraone

  DOI：10.1002/ejic.201100113

  日期：2011.6

  This work was supported by Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR), PRIN 2007HMTJWP_005

  这项工作得到了Ministryo dell'Istruzione, dell'Universita e della Ricerca (MIUR), PRIN 2007HMTJWP_005 的支持