(3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoic acid | 162998-91-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoic acid
• 英文别名: (3R)-3-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoic acid；(3R)-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 162998-91-6
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: WUIQVOMIYLNNEC-MRXNPFEDSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  526.7±50.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoic acid 在 钯 lithium aluminium tetrahydride 、 氢气 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)

  摘要：

  Inhibition of interleukin-1 beta converting enzyme (ICE), apopain, papain, thrombin and trypsin with substrate like peptidyl L- and D-alpha-aldehydes and their L-beta-homo-aldehyde analogues was investigated. The L-beta-homo-aspartals appear to be specific inhibitors for ICE and its homologues; the other enzymes were not inhibited with such L-beta-homo aldehydes. Papain shows tolerance for D-residues at P-1 depending on their chiral stability. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00244-3
• 作为产物：
  描述：

  (3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 生成 (3R)-N-(benzyloxycarbonyl)-3-amino-4-phenylbutanoic acid
  参考文献：
  名称：

  Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)

  摘要：

  Inhibition of interleukin-1 beta converting enzyme (ICE), apopain, papain, thrombin and trypsin with substrate like peptidyl L- and D-alpha-aldehydes and their L-beta-homo-aldehyde analogues was investigated. The L-beta-homo-aspartals appear to be specific inhibitors for ICE and its homologues; the other enzymes were not inhibited with such L-beta-homo aldehydes. Papain shows tolerance for D-residues at P-1 depending on their chiral stability. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00244-3

文献信息

• Nonhydrolyzable d‑phenylalanine-benzoxazole derivatives retain antitubercular activity
  作者：Michael J. Pepi、Shibin Chacko、Nicole Kopetz、Helena I.M. Boshoff、Gregory D. Cuny、Lizbeth Hedstrom

  DOI：10.1016/j.bmcl.2022.129116

  日期：2023.1

  emergence of drug resistant Mycobacterium tuberculosis, the causative agent of tuberculosis, demands the development of new drugs and new drug targets. We have recently reported that the d-phenylalanine benzoxazole Q112 has potent antibacterial activity against this pathogen with a distinct mechanism of action from other antimycobacterial agents. Q112 and previously reported derivatives were unstable in

  结核病的病原体——耐药结核分枝杆菌的出现，需要开发新药和新的药物靶点。我们最近报道， d-苯丙氨酸苯并恶唑Q112对这种病原体具有有效的抗菌活性，其作用机制与其他抗分枝杆菌药物不同。 Q112和之前报道的衍生物在血浆中不稳定，没有观察到游离化合物。在这里，我们扩展了抗分枝杆菌活性的结构-活性关系，并发现了血浆结合减少的不可水解衍生物。我们还表明，抗菌活性和对 PanG 的抑制之间不存在相关性，PanG 是这些化合物的假定靶点。
• A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives
  作者：David A. Evans、Leester D. Wu、John J. M. Wiener、Jeffrey S. Johnson、David H. B. Ripin、Jason S. Tedrow

  DOI：10.1021/jo990756k

  日期：1999.8.1

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).
• Vasanthakumar; Babu, V. V. Suresh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1691 - 1695
  作者：Vasanthakumar、Babu, V. V. Suresh

  DOI：——

  日期：——