N-Boc-L-Pha-OAc | 121778-78-7

• 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: N-Boc-L-Pha-OAc
• 英文别名: 2-(tert-butoxycarbonylamino)-3-phenylpropyl acetate；[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropyl] acetate
• CAS: 121778-78-7
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: ICTHCNRDSVFMDL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-L-Pha-OAc 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 (S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methylbutanamido)-3-phenylpropyl acetate
  参考文献：
  名称：

  Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents

  摘要：

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.

  DOI：

  10.1111/j.1747-0285.2012.01331.x
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 N-甲基吗啉 、 吡啶 、 氯甲酸异丁酯 作用下， 以 乙腈 为溶剂， 反应 1.17h， 生成 N-Boc-L-Pha-OAc
  参考文献：
  名称：

  Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents

  摘要：

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.

  DOI：

  10.1111/j.1747-0285.2012.01331.x

文献信息

• Rapid and facile Lewis acid catalysed Boc protection of amines
  作者：G.V.M. Sharma、J. Janardhan Reddy、P. Sree Lakshmi、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2004.07.072

  日期：2004.9

  Efficient Boc protection of amines was carried out using (Boc)2O in the presence of a catalytic amount of ZrCl4 (10 mol %) in acetonitrile at room temperature. The reaction times are very short and the yields are generally high.

  在室温下，在乙腈中催化量的ZrCl 4（10 mol％）存在下，使用（Boc）2 O对胺进行有效的Boc保护。反应时间非常短，并且产率通常很高。
• Absolute Stereo-structure of Kendarimide A, a Novel MDR Modulator, from a Marine Sponge
  作者：Motomasa Kobayashi、Naoyuki Kotoku、Liwei Cao、Shunji Aoki

  DOI：10.3987/com-04-10287

  日期：——