5-(trimethylsilyl)-1,3-oxazole | 869542-48-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-(trimethylsilyl)-1,3-oxazole
• 英文别名: 2-(trimethylsilyl)oxazole；5-(Trimethylsilyl)oxazole；trimethyl(1,3-oxazol-5-yl)silane
• CAS: 869542-48-3
• 化学式: C₆H₁₁NOSi
• 分子量: 141.245
• InChiKey: CDHUODUPLDBZEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzyloxycarbonyl-L-valyl-L-prolyl-L-valinal 、 5-(trimethylsilyl)-1,3-oxazole 以 甲苯 为溶剂， 以53%的产率得到(benzyloxycarbonyl)-L-valyl-N-<1-<(2-oxazolyl)hydroxymethyl>-2-methylpropyl>-L-prolinamide
  参考文献：
  名称：

  Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency

  摘要：

  A series of peptidyl alpha-ketoheterocycles were synthesized and evaluated for their in vitro inhibition of human neutrophil elastase (HNE). Several heterocycles, including oxazoline and benzoxazole, afforded extremely potent inhibitors of HNE (1p-r) with nanomolar to subnanomolar K-i values. The structure-activity relationships revealed that for compounds with a K-i < 1000 nM potency tends to be positively correlated with the sigma(I) value of the heterocycle. Furthermore, the results in this study support the hypothesis that, in the covalent enzyme-inhibitor adduct, the azole nitrogen atom of the inhibitor heterocycle participates in a hydrogen-bonding interaction with the active-site His-57.

  DOI：

  10.1021/jm00001a013
• 作为产物：
  描述：

  5-(trimethylsilyl)-2-[tris(1-methylethyl)silyl]-1,3-oxazole 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以90%的产率得到5-(trimethylsilyl)-1,3-oxazole
  参考文献：
  名称：

  方便的恶唑C-2保护基团：通过2-三异丙基甲硅烷基恶唑的金属化合成4-和5-取代的恶唑

  摘要：

  区域选择性的C-2甲硅烷基保护后，在4和5位上的恶唑金属化。然后在温和的条件下完成保护基的去除，从而可以直接制备C-5单取代的和C-4,5-二取代的恶唑。已经证明了恶唑的第一个实用的C-2保护基。

  DOI：

  10.1021/jo051490m

文献信息

• Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency
  作者：Philip D. Edwards、Donald J. Wolanin、Donald W. Andisik、Matthew W. Davis

  DOI：10.1021/jm00001a013

  日期：1995.1

  A series of peptidyl alpha-ketoheterocycles were synthesized and evaluated for their in vitro inhibition of human neutrophil elastase (HNE). Several heterocycles, including oxazoline and benzoxazole, afforded extremely potent inhibitors of HNE (1p-r) with nanomolar to subnanomolar K-i values. The structure-activity relationships revealed that for compounds with a K-i < 1000 nM potency tends to be positively correlated with the sigma(I) value of the heterocycle. Furthermore, the results in this study support the hypothesis that, in the covalent enzyme-inhibitor adduct, the azole nitrogen atom of the inhibitor heterocycle participates in a hydrogen-bonding interaction with the active-site His-57.
• A Convenient Oxazole C-2 Protecting Group:  The Synthesis of 4- and 5-Substituted Oxazoles via Metalation of 2-Triisopropylsilyloxazoles
  作者：Ross A. Miller、Randi M. Smith、Benjamin Marcune

  DOI：10.1021/jo051490m

  日期：2005.10.1

  Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated.

  区域选择性的C-2甲硅烷基保护后，在4和5位上的恶唑金属化。然后在温和的条件下完成保护基的去除，从而可以直接制备C-5单取代的和C-4,5-二取代的恶唑。已经证明了恶唑的第一个实用的C-2保护基。