(R)-3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-butyric acid tert-butyl ester

• 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: (R)-3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-butyric acid tert-butyl ester
• 英文别名: tert-butyl (3R)-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)butanoate
• 化学式: C₃₀H₃₁NO₂
• 分子量: 437.582
• InChiKey: MEPGYHCQYSWAFO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-butyric acid tert-butyl ester 在 palladium dihydroxide morpholinium formate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (3R)-3-氨基丁酸叔丁酯
  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
• 作为产物：
  描述：

  巴豆酸叔丁酯 、 (S)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine 在 正丁基锂 作用下， 生成 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)butanoate 、 (R)-3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-butyric 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

文献信息

• An asymmetric ammonia synthon for Michael additions
  作者：Joel M. Hawkins、Timothy A. Lewis

  DOI：10.1021/jo00033a037

  日期：1992.3

  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.