(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pent-2-enoic acid ethyl ester | 143250-65-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pent-2-enoic acid ethyl ester
• CAS: 143250-65-1
• 化学式: C₂₈H₄₀N₂O₄Si
• 分子量: 496.722
• InChiKey: GSNYEVLYPRTCBO-SUOUMBACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pent-2-enoic acid ethyl ester 在 铑 、 2,5-降冰片二烯 、 1,4-双(二苯基膦)丁烷 氢气 作用下， 以 甲醇 为溶剂， 反应 45.0h， 生成 (R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pentanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of α,γ -diamino acid esters

  摘要：

  Chiral didehydro amino acid esters 2/3 derived from amino acids are hydrogenated stereoselectively with rhodium catalysts based on achiral ligands, the alpha,gamma-diamino acid derivatives 4 being the major products. The sense and degree of stereoselectivity can be influenced to some extent by the use of chiral diphosphines. The iridium-containing Crabtree-catalyst is particularly effective in the case of the serine derivative 2 (R1 = HOCH2).

  DOI：

  10.1016/0957-4166(92)80010-t
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pent-2-enoic acid ethyl ester 、 (E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-dibenzylamino-2-formylamino-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Cycloaddition reactions of λ-amino α,β-didehydro amino acid esters: a test case for the principle of 1,3-allylic strain

  摘要：

  N,N-Dibenzylainino aldehydes, readily accessible from amino acids, can be converted into gamma-N,N-dibenzylamino alpha,beta-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain.

  DOI：

  10.1016/s0040-4039(00)92661-3