tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate | 167770-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate
• 英文别名: tert-butyl N-[(3S)-1-bromo-2-oxo-5-phenylpentan-3-yl]carbamate
• CAS: 167770-19-6
• 化学式: C₁₆H₂₂BrNO₃
• 分子量: 356.26
• InChiKey: CYQCRRDYJWQEJS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate 在 potassium fluoride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-amino-2-oxo-5-phenylpentyl 2,5-dichlorobenzoate toluenesulfonic acid salt
  参考文献：
  名称：

  Novel route to the synthesis of peptides containing 2-amino-1′-hydroxymethyl ketones and their application as cathepsin K inhibitors

  摘要：

  Cathepsin K is highly expressed in human osteoclasts, and is implicated in bone resorption. This makes it an attractive target for the treatment of osteoporosis. Peptides containing 2-amino-1'-hydroxymethyl ketones and 2-amino-1'-alkoxymethyl ketones were discovered as potent inhibitors of cathepsin K. A novel synthetic route was devised to facilitate rapid elucidation of the SAR of these inhibitors. The synthesis and SAR of hydroxymethyl ketones are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00611-x
• 作为产物：
  描述：

  Boc-L-高苯丙氨酸 在 N-methylmorpholinepolystyrene 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.2h， 生成 tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate
  参考文献：
  名称：

  通过三氟甲磺酸金属盐催化的分子内重氮羰基分子插入反应，由Boc保护的氨基酸有效合成环状氨基甲酸酯

  摘要：

  本文描述了由重氮酮3a - 1简单有效地合成环状氨基甲酸酯和相关的恶嗪酮1a - l的方法。该转化涉及在分子内重氮羰基插入反应中使用金属三氟甲磺酸酯通过重氮基团的活化而生成羧甲酸酯，总收率很高。

  DOI：

  10.1016/j.tetlet.2006.08.111

文献信息

• Compounds and compositions as protease inhibitors
  申请人：Axys Pharmaceuticals, Inc.

  公开号：US06506733B1

  公开（公告）日：2003-01-14

  Compounds of the formula: are provided, and are useful as cysteine protease inhibitors, particularly in the treatment of diseases such as osteoporosis or autoimmune disorders in which cathepsins K or S contribute to the pathology or symptomatolgy of the disease.

  提供了公式为的化合物，其作为半胱氨酸蛋白酶抑制剂具有用处，特别是在治疗疾病方面，如骨质疏松或自身免疫性疾病，其中猫蛋白酶K或S对疾病的病理学或症状学有贡献。
• Novel compounds and compositions as protease inhibitors
  申请人：Axys Pharmaceuticals, Inc.

  公开号：US20030092634A1

  公开（公告）日：2003-05-15

  The present invention relates to novel cysteine protease inhibitors; the pharmaceutically acceptable salts and N-oxides thereof; their uses as therapeutic agents and the methods of their making.

  本发明涉及新型半胱氨酸蛋白酶抑制剂；其药学上可接受的盐和N-氧化物；它们作为治疗剂的用途和其制备方法。
• Oh, Seikwan; Jung, Jae-Chul, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2008, vol. 63, # 2, p. 210 - 216
  作者：Oh, Seikwan、Jung, Jae-Chul

  DOI：——

  日期：——
• An efficient synthesis of cyclic urethanes from Boc-protected amino acids through a metal triflate-catalyzed intramolecular diazocarbonyl insertion reaction
  作者：Jae-Chul Jung、Mitchell A. Avery

  DOI：10.1016/j.tetlet.2006.08.111

  日期：2006.11

  A simple and efficient synthesis of cyclic urethanes and related oxazinanones 1a–l from diazoketones 3a–l is described. The transformation involves generation of carbenes by activation of diazo groups using metal triflates in intramolecular diazocarbonyl insertion reactions in high overall yields.

  本文描述了由重氮酮3a - 1简单有效地合成环状氨基甲酸酯和相关的恶嗪酮1a - l的方法。该转化涉及在分子内重氮羰基插入反应中使用金属三氟甲磺酸酯通过重氮基团的活化而生成羧甲酸酯，总收率很高。
• Novel route to the synthesis of peptides containing 2-amino-1′-hydroxymethyl ketones and their application as cathepsin K inhibitors
  作者：Rohan V Mendonca、Shankar Venkatraman、James T Palmer

  DOI：10.1016/s0960-894x(02)00611-x

  日期：2002.10

  Cathepsin K is highly expressed in human osteoclasts, and is implicated in bone resorption. This makes it an attractive target for the treatment of osteoporosis. Peptides containing 2-amino-1'-hydroxymethyl ketones and 2-amino-1'-alkoxymethyl ketones were discovered as potent inhibitors of cathepsin K. A novel synthetic route was devised to facilitate rapid elucidation of the SAR of these inhibitors. The synthesis and SAR of hydroxymethyl ketones are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.