(S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine

• 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: (S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine
• 英文别名: (Sa)-2-{3H-dinaphtho[2,1-c:1',2'-e]azepin-4(5H)-yl}-N,N-dimethylethanamine；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)-N,N-dimethylethanamine
• 化学式: C₂₆H₂₆N₂
• 分子量: 366.506
• InChiKey: ABGPHIVJRGRMLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine 、 氢化铝锂 以78%的产率得到
  参考文献：
  名称：

  COTTINEAU, F.;MAIGROT, N.;MAZALEYRAT, J. -P., TETRAHEDRON LETT., 1985, 26, N 4, 421-424

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2,2'-双(溴甲基)-1,1'-联萘 、 N,N-二甲基乙二胺 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine
  参考文献：
  名称：

  在旋光的1,1'-联萘二胺衍生物存在下，四氧化对烯烃的对映选择性二羟基化

  摘要：

  由Cram和Mazaleyrat引入的手性二胺（S）-1已按照涉及二酸（RS）-3拆分的不同顺序进行了重新制备。已确定（S）-1的ee（通过HPLC和NMR），绝对构型（通过CD）和最稳定的构象（通过UV和分子力学计算）。（S）-1已被用作烯烃的化学计量顺式-二羟基化中的手性助剂，从而获得了具有高达98％的ee的旋光的1,2-二醇。

  DOI：

  10.1016/0957-4166(96)00388-6

文献信息

• 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
• Reductive cleavage of axially disymmetric tertiary amines and quaternary ammonium salts by lithium aluminium hydride. Synthesis of new 1,1′-binaphthyl substituted amines
  作者：Frédéric Cottineau、Nicole Maigrot、Jean-Paul Mazaleyrat

  DOI：10.1016/s0040-4039(00)61900-7

  日期：1985.1

  Axially disymmetric tertiary amines or quaternary ammonium salts A are synthesized by double alkylation of primary or secondary amines with racemic or optically pure 2,2′-bis (bromomethyl)-1,1′-binaphthyl. Their reductive cleavage by lithium aluminium hydride in refluxing THF leads to chiral secondary or tertiary amines B, substituted by a binaphthyl unit, with high yields and absence of racemization

  轴向二对称的叔胺或季铵盐A是通过将伯胺或仲胺与外消旋或光学纯的2,2'-双（溴甲基）-1,1'-联萘基进行双烷基化反应而合成的。它们在回流的THF中被氢化铝锂还原裂解，得到手性仲或叔胺B，被双萘基单元取代，收率高且没有外消旋作用。
• Chiral catalysis of additions of alkyllithiums to aldehydes
  作者：Jean Paul Mazaleyrat、Donald J. Cram

  DOI：10.1021/ja00405a052

  日期：1981.7
• Synthesis and resolution of axially chiral C2-symmetric 1,1′-binaphthyl-substituted tetramethylethylenediamines
  作者：Jean-Paul Mazaleyrat

  DOI：10.1016/s0957-4166(97)00301-7

  日期：1997.8

  The axially chiral TMEDA derivatives 1 and 2 in which tetramethylethylene-diamine is substituted respectively by one and two 1,1'-binaphthyl units at their 2,2'positions, are of interest as chiral catalysts. Experimental details of their preparation in enantiomerically pure form are given. Two different routes have been followed, involving alkylation of both N,N-dimethyl ethylenediamine and ethylenediamine by 2,2'bis-(bromomethyl)-1,1'-binaphthyl either enantiomerically pure as prepared from resolved 1,1'-binaphthyl-2,2'-dicarboxylic acid or racemic, the resulting racemic diamines 1 and 2 being then resolved with dibenzoyl-tartaric acid. (C) 1997 Elsevier Science Ltd.
• SUMIDA, XIROSI;KANAJ, SIGEHESI
  作者：SUMIDA, XIROSI、KANAJ, SIGEHESI

  DOI：——

  日期：——