[5-(allyloxycarbonylamino)-6-oxo-hexyl]-carbamic acid tert-butyl ester | 188947-18-4

• 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: [5-(allyloxycarbonylamino)-6-oxo-hexyl]-carbamic acid tert-butyl ester
• CAS: 188947-18-4
• 化学式: C₁₅H₂₆N₂O₅
• 分子量: 314.382
• InChiKey: WHFBQPFSUQNIRS-LBPRGKRZSA-N

物化性质

• 沸点：
  460.4±45.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [5-(allyloxycarbonylamino)-6-oxo-hexyl]-carbamic acid tert-butyl ester 在 咪唑 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 羟胺 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 [5-amino-6-{5-[4-(3,4-dichlorophenethyloxy)phenylmethyl]-[1,2,4]oxadiazol-3-yl}-6-(tert-butyl-dimethylsilyloxy)-hexyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of selective keto-1,2,4-oxadiazole-based tryptase inhibitors

  摘要：

  Using a scaleable, directed library approach based on orthogonally protected advanced intermediates, we have prepared a series of potent keto-1,2,4-oxadiazoles designed to explore the P-2 binding pocket of human mast cell tryptase, while building in a high degree of selectivity over human trypsin and other serine proteases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.013
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 [5-(allyloxycarbonylamino)-6-oxo-hexyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of selective keto-1,2,4-oxadiazole-based tryptase inhibitors

  摘要：

  Using a scaleable, directed library approach based on orthogonally protected advanced intermediates, we have prepared a series of potent keto-1,2,4-oxadiazoles designed to explore the P-2 binding pocket of human mast cell tryptase, while building in a high degree of selectivity over human trypsin and other serine proteases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.013

文献信息

• WO2006/44133
  申请人：——

  公开号：——

  公开（公告）日：——
• Peptidyl α-keto thiazole as potent thrombin inhibitors
  作者：Yoshihisa Akiyama、Seiji Tsutsumi、Emiko Hatsushiba、Shoukichi Ohuchi、Tsuneo Okonogi

  DOI：10.1016/s0960-894x(97)00057-7

  日期：1997.3

  We report the synthesis and evaluation of alpha-keto thiazole derivatives such as D-Phe-Pro-Arg-thiazole 9 as a novel type of thrombin inhibitor. Tripeptidyl alpha-keto thiazole 9 exhibited the inhibitory activity of thrombin at nanomolar levels and showed a more potent prolongation effect on clotting time than argatroban at a dose of 3 mg/kg intravenously. (C) 1997 Elsevier Science Ltd.
• Design and synthesis of selective keto-1,2,4-oxadiazole-based tryptase inhibitors
  作者：James T. Palmer、Robert M. Rydzewski、Rohan V. Mendonca、David Sperandio、Jeffrey R. Spencer、Bernard L. Hirschbein、Julia Lohman、Jeri Beltman、Margaret Nguyen、Liang Liu

  DOI：10.1016/j.bmcl.2006.04.013

  日期：2006.7

  Using a scaleable, directed library approach based on orthogonally protected advanced intermediates, we have prepared a series of potent keto-1,2,4-oxadiazoles designed to explore the P-2 binding pocket of human mast cell tryptase, while building in a high degree of selectivity over human trypsin and other serine proteases. (c) 2006 Elsevier Ltd. All rights reserved.