methyl 11-((tert-butoxycarbonyl)amino)undecanoate | 773073-16-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 11-((tert-butoxycarbonyl)amino)undecanoate
• 英文别名: Methyl 11-[(2-methylpropan-2-yl)oxycarbonylamino]undecanoate
• CAS: 773073-16-8
• 化学式: C₁₇H₃₃NO₄
• 分子量: 315.453
• InChiKey: NZGVKNZTEKFFLM-UHFFFAOYSA-N

物化性质

• 沸点：
  401.4±18.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  methyl 11-((tert-butoxycarbonyl)amino)undecanoate 在 盐酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Understanding the Metabolism of Proteolysis Targeting Chimeras (PROTACs): The Next Step toward Pharmaceutical Applications

  摘要：

  Hetero-bifunctional PROteolysis TArgeting Chimeras (PROTACs) represent a new emerging class of small molecules designed to induce polyubiquitylation and proteasomal-dependent degradation of a target protein. Despite the increasing number of publications about the synthesis, biological evaluation, and mechanism of action of PROTACs, the characterization of the pharmacokinetic properties of this class of compounds is still minimal. Here, we report a study on the metabolism of a series of 40 PROTACs in cryopreserved human hepatocytes at multiple time points. Our results indicated that the metabolism of PROTACs could not be predicted from that of their constituent ligands. Their linkers' chemical nature and length resulted in playing a major role in the PROTACs' liability. A subset of compounds was also tested for metabolism by human cytochrome P450 3A4 (CYP3A4) and human aldehyde oxidase (hAOX) for more in-depth data interpretation, and both enzymes resulted in active PROTAC metabolism.

  DOI：

  10.1021/acs.jmedchem.0c00793
• 作为产物：
  描述：

  甲醇 、 叔丁氧羰基-11-氨基十一烷酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 methyl 11-((tert-butoxycarbonyl)amino)undecanoate
  参考文献：
  名称：

  Anti-HIV agents with dual sites of action

  摘要：

  本发明提供了一般结构为：1的化合物，该化合物在3和28位置被取代，以及含有该化合物的药物配方以及使用该化合物治疗病毒感染的方法。

  公开号：

  US20040204389A1

文献信息

• Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
  作者：Muriel Amatore、Teresa D. Beeson、Sean P. Brown、David W. C. MacMillan

  DOI：10.1002/anie.200901855

  日期：2009.6.29

  Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α‐chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

  SOme MOre 时间：首次利用 SOMO（单占据分子轨道）激活来实现醛的 α-氯化的新方法。这种转化可以很容易地作为对映选择性生产末端环氧化物的关键催化方法的一部分来实现。
• Ring‐Opening Amino Esterification of Cyclic Ketones to Access Distal Amino Acid Derivatives
  作者：Ishin Tomiya、Yuhao Wu、Kengo Hyodo

  DOI：10.1002/adsc.202301421

  日期：2024.4.9

  synthesizing distal amino acid derivatives by the ring-opening reaction of cyclic ketones, following the amino esterification functionalization of both terminals. To achieve this goal, we performed the ring-opening reaction of cyclic ketones with an aminating reagent and alcohol under metal- and photocatalysis-free conditions in a single step. The method directly afforded distal amino acid derivatives bearing

  本研究开发了一种通过环酮的开环反应，然后对两个末端进行氨基酯化功能化来合成远端氨基酸衍生物的方法。为了实现这一目标，我们在无金属和光催化条件下一步进行了环酮与胺化试剂和醇的开环反应。该方法直接提供带有C4-C6、C8和C12碳主链的远端氨基酸衍生物，例如γ、δ和ε-氨基酯。获得的氨基酯通过水解简单地转化为氨基酸。