3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-4-methyl-pentanoic acid tert-butyl ester | 138922-51-7

• 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: 3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-4-methyl-pentanoic acid tert-butyl ester
• 英文别名: tert-butyl 3-(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)-4-methylpentanoate
• CAS: 138922-51-7
• 化学式: C₃₂H₃₅NO₂
• 分子量: 465.635
• InChiKey: FTVPDSKALYCTEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  tert-butyl (E)-4-methylpent-2-enoate 、 (RS)-3,5-dihydro-4H-dinaphth[2,1-c:1',2'-e]azepine 在 三乙胺 作用下， 以7.4%的产率得到3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-4-methyl-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  An asymmetric ammonia synthon for Michael additions

  摘要：

  The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.

  DOI：

  10.1021/jo00033a037