O-<(trimethylsilyl)ethyl>diisopropylisourea | 131618-25-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: O-<(trimethylsilyl)ethyl>diisopropylisourea
• 英文别名: O-[2-(trimethylsilyl)ethyl] diisopropyl isourea；2-(Trimethylsilyl)ethyl N,N-dipropan-2-ylcarbamimidate；2-trimethylsilylethyl N,N-di(propan-2-yl)carbamimidate
• CAS: 131618-25-2
• 化学式: C₁₂H₂₈N₂OSi
• 分子量: 244.453
• InChiKey: VLIURVUGWIEEFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  36.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-<(trimethylsilyl)ethyl>diisopropylisourea 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester
  参考文献：
  名称：

  Synthesis of foroxymithine, a microbial fermentation product and angiotensin 1 converting enzyme inhibitor

  摘要：

  The first total synthesis of the microbial fermentation product, ferric ion chelator and angiotensin converting enzyme inhibitor foroxymithine 1 is described. In addition to firmly establishing the reported structure of 1, a flexible synthetic strategy was employed which will allow the future syntheses of various derivatives and conjugates. Use of the chiral building block L-glutamic acid and conversion to the protected delta-hydroxynorvaline 3, followed by synthesis of the protected hydroxamic acids 4 and 5, afforded the precursor fragments needed. A series of peptide coupling reactions, including the problems encountered and conditions devised for the formation of the diketopiperazine 13 in good yield, are discussed. Finally, coupling of the left- and right-hand fragments, acetylation, deprotection, and hydrogenolysis gave foroxymithine 1.

  DOI：

  10.1021/jo00002a005

文献信息

• Oxime derivatives of sordaricin as potent antifungal agents
  作者：Michael H. Serrano-Wu、Denis R. St. Laurent、Charles E. Mazzucco、Terry M. Stickle、John F. Barrett、Dolatrai M. Vyas、Balu N. Balasubramanian

  DOI：10.1016/s0960-894x(02)00054-9

  日期：2002.3

  Oxime derivatives of the sordarin aglycone have been identified as potent antifungal agents. The in vitro spectrum of activity includes coverage against Candida alhicans and Candida glabrata with MICs as low as 0.06 mug/mL. The antifungal activity was established to be exquisitely sensitive to the spatial orientation of the lipophilic side chains. (C) 2002 Elsevier Science Ltd. All rights reserved.