(S)-2-[(S)-2-[[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]diphenylsilanyl]methyl]-4-methylpentanoylamino]-4-methylpentanoic acid tert-butyl ester | 561294-36-8

• 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: (S)-2-[(S)-2-[[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]diphenylsilanyl]methyl]-4-methylpentanoylamino]-4-methylpentanoic acid tert-butyl ester
• CAS: 561294-36-8
• 化学式: C₃₈H₄₈N₂O₅Si
• 分子量: 640.895
• InChiKey: PXIIPRAPEWJSKZ-YDYNHKSESA-N

物化性质

• 沸点：
  710.2±60.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-2-[[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]diphenylsilanyl]methyl]-4-methylpentanoylamino]-4-methylpentanoic acid tert-butyl ester 在 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到(S)-2-[(S)-2-[[(aminomethyl)diphenylsilanyl]methyl]-4-methylpentanoylamino]-4-methylpentanoic acid tert-butyl ester
  参考文献：
  名称：

  A Silanediol Inhibitor of the Metalloprotease Thermolysin:  Synthesis and Comparison with a Phosphinic Acid Inhibitor¹

  摘要：

  A silanediol inhibitor of the metalloprotease thermolysin was prepared for comparison to a known phosphinic acid inhibitor, providing the first comparison of these second-row element based transition-state analogues. Inhibition of thermolysin by the silanediol (K-i = 41 nM) was comparable to that of the phosphinic acid (K-i = 10 nM) even though the silanediol is uncharged and thereby lacks the intrinsic Coulombic attraction of the phosphinate anion to the active-site zinc cation. This silanediol protease inhibitor is the least sterically encumbered example prepared to date and, therefore, the most prone toward polymerization. Hydrolysis of a difluorosilane intermediate to the silanediol leads cleanly to a monomeric product.

  DOI：

  10.1021/jo049929i
• 作为产物：
  描述：

  苯基氯化镁 在 sodium chlorite 、 四丙基高钌酸铵 、 氢氟酸 、 三溴化硼 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[(S)-2-[[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]diphenylsilanyl]methyl]-4-methylpentanoylamino]-4-methylpentanoic acid tert-butyl ester
  参考文献：
  名称：

  Silanediol-Based inhibitor of thermolysin

  摘要：

  The first silanediol inhibitor of thermolysin is reported, prepared by analogy with the Grobelny/Bartlett phosphinate inhibitor. A Cbz group on nitrogen proved to be unstable to the triflic acid mediated silanediol deprotection and was replaced with a dihydrocinnamoyl group. The silanediol was prepared in high purity by hydrolysis of a difluorosilane intermediate and proved to be an effective inhibitor, differing from the phosphinate by a factor of 4 (K-i = 41 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00804-1