| 138878-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• CAS: 138878-05-4；138922-53-9；138922-54-0；138922-55-1
• 化学式: C₃₈H₄₉NO₃Si
• 分子量: 595.897
• InChiKey: QQLSTDXKJUPWBU-OOOSNSGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.73
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 palladium dihydroxide 4-二甲氨基吡啶 、 ammonium formate 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 13.25h， 生成 3-Amino-4-methylvalerolactone, 1-naphthamide
  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：

  (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester 在 正丁基锂 、 硼烷四氢呋喃络合物 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成
  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