N-<(1R-(1α,2α,3α))-2-(hydroxymethyl)-3-(2-propyl)-cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide | 149859-35-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-<(1R-(1α,2α,3α))-2-(hydroxymethyl)-3-(2-propyl)-cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide
• 英文别名: (1R,2S,3R)-2-(hydroxymethyl)-N-[(4-methoxyphenyl)methyl]-N-[(2S)-3-(4-methoxyphenyl)-1-(methylamino)-1-oxopropan-2-yl]-3-propan-2-ylcyclopropane-1-carboxamide
• CAS: 149859-35-8
• 化学式: C₂₇H₃₆N₂O₅
• 分子量: 468.593
• InChiKey: XQROYMLYNJGJKF-JBXUNAHCSA-N

物化性质

• 沸点：
  700.3±60.0 °C(predicted)
• 密度：
  1.159±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-<(1R-(1α,2α,3α))-2-(hydroxymethyl)-3-(2-propyl)-cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以75%的产率得到N-<(1R-(1α,2α,3α))-2-formyl-3-(2-propyl)cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide
  参考文献：
  名称：

  Cyclopropanes as conformationally restricted peptide isosteres. Design and synthesis of novel collagenase inhibitors

  摘要：

  The 1,2,3-trisubstituted cyclopropane derivatives 9 and 10 were prepared as conformationally constrained analogues of the known collagenase inhibitor 8. The syntheses of 9 and 10 featured the highly enantioselective Rh2[S-MEPY]4 catalyzed cyclization of the, allylic diazo ester 11 to give the lactone 13. Opening of the lactone ring of 13 with N,O-di-(p-methoxybenzyl)hydroxylamine under Weinreb conditions followed by refunctionalization, coupling of the intermediate acid 16 with 17 and deprotection led to the dipeptide analogue 9. Alternatively, the lactone ring of 13 could be opened with the protected tyrosine 21 by a novel variant of the Weinreb protocol to give directly the dipeptide analogue 22 which was then converted into 10.

  DOI：

  10.1016/s0040-4020(01)90212-1
• 作为产物：
  描述：

  N^α-tert-butyloxycarbonyl-O-methyl-(S)-tyrosine methylamide 在 盐酸 、 sodium tetrahydroborate 、 3 A molecular sieve 、 三甲基铝 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 37.0h， 生成 N-<(1R-(1α,2α,3α))-2-(hydroxymethyl)-3-(2-propyl)-cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide
  参考文献：
  名称：

  Cyclopropanes as conformationally restricted peptide isosteres. Design and synthesis of novel collagenase inhibitors

  摘要：

  The 1,2,3-trisubstituted cyclopropane derivatives 9 and 10 were prepared as conformationally constrained analogues of the known collagenase inhibitor 8. The syntheses of 9 and 10 featured the highly enantioselective Rh2[S-MEPY]4 catalyzed cyclization of the, allylic diazo ester 11 to give the lactone 13. Opening of the lactone ring of 13 with N,O-di-(p-methoxybenzyl)hydroxylamine under Weinreb conditions followed by refunctionalization, coupling of the intermediate acid 16 with 17 and deprotection led to the dipeptide analogue 9. Alternatively, the lactone ring of 13 could be opened with the protected tyrosine 21 by a novel variant of the Weinreb protocol to give directly the dipeptide analogue 22 which was then converted into 10.

  DOI：

  10.1016/s0040-4020(01)90212-1