2-叔-丁基氧羰基氨基-5-庚烯酸 | 119808-36-5

• 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
• 中文名称: 2-叔-丁基氧羰基氨基-5-庚烯酸
• 中文别名: 6-庚烯酸,2-[[(1,1-二甲基乙氧基)羰基]氨基]-
• 英文名称: 2-tert-butoxycarbonylamino-hept-6-enoic acid
• 英文别名: 2-tert-Butyloxycarbonylamino-5-heptenoic Acid；2-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-enoic acid
• CAS: 119808-36-5
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: WPKPUPUWFHDYRR-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70oC
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-叔-丁基氧羰基氨基-5-庚烯酸 在 Hoveyda-Grubbs catalyst second generation 、 三异丙基硅烷 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 46.0h， 生成
  参考文献：
  名称：

  大型宏周期库的面向多样性的方法

  摘要：

  基于“构建/偶联/配对”策略的面向多样性的大环化合物库方法可用于生成1.8⋅10 5种化合物的虚拟化学空间，并有可能通过“配对后”修饰进一步扩展。该方法依靠4-5个反应步骤，其中包括闭环复分解为关键步骤，在平行化学条件下的总合成效率为61％。

  DOI：

  10.1002/ejoc.202100195
• 作为产物：
  描述：

  ethyl 2-tert-butoxycarbonylamino-hept-6-enoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 乙醇 为溶剂， 以94%的产率得到2-叔-丁基氧羰基氨基-5-庚烯酸
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Boronic Acid-Based Histone Deacetylase Inhibitors

  摘要：

  Guided by the proposed catalytic mechanism of histone deacetylases (HDACs), we designed and synthesized a series of boronic acid-based HDAC inhibitors bearing an alpha-amino acid moiety. In this series, compounds (S)-18, 20, and 21 showed potent HDAC-inhibitory activity, highlighting the significance of the (S)-amino acid moiety. In cancer cell growth inhibition assays, compounds (S)-18. 20, and 21 exerted strong activity, and the values of the ratio of the concentration causing 50% growth inhibition (GI(50)) to the concentration causing 50% enzyme inhibition (IC50), i.e., GI(50)/IC50, were low. The potency of these compounds was similar to that of clinically used suberoylanilide hydroxamic acid (SAHA) (2). The results of Western blot analysis indicated that the-cancer cell growth-inhibitory activity of compounds (S)-18, 20, and 21 is the result of HDAC inhibition. A molecular modeling study suggested that the hydrated boronic acid interacts with zinc ion, Tyr residue, and His residue in the active site of HDACs. Our findings indicate that these boronic acid derivatives represent an entry into a new class of HDAC inhibitors.

  DOI：

  10.1021/jm900125m

文献信息

• Use of the Claisen/metathesis reaction sequence for the synthesis of enantiomerically pure 1-aminocycloalkene-1-carboxylic acids
  作者：Karen Plé、Arnaud Haudrechy、Nicolas P. Probst

  DOI：10.1016/j.tet.2010.05.008

  日期：2010.7

  the preparation of enantiomerically pure 1-aminocycloalkene-1-carboxylic acids is reported using a chelate Claisen rearrangement–metathesis sequence. Enantioselectivity is achieved through substrate control and a highly ordered transition state, without the use of a chiral auxiliary. A synthesis of 1-aminocyclopent-3-ene-1-carboxylic acid 1 in five steps and 47% overall yield is also described.

  据报道，使用螯合的克莱森重排-复分解序列可以有效地制备对映体纯的1-氨基环烯-1-羧酸。对映选择性是通过底物控制和高度有序的过渡态实现的，无需使用手性助剂。还描述了通过五个步骤合成1-氨基环戊-3-烯-1-羧酸1并且总产率为47％的方法。
• Inhibitors of hepatitis C virus
  申请人：——

  公开号：US20040038872A1

  公开（公告）日：2004-02-26

  The present invention relates to macrocyclic compounds, methods for making these compounds, pharmaceutical compositions and the therapeutic or prophylactic use of these compounds by administering said compounds to mammals to prevent or treat hepatitis C virus (HCV) infection.

  本发明涉及大环化合物、制备这些化合物的方法、药物组合物以及通过将这些化合物给哺乳动物预防或治疗丙型肝炎病毒（HCV）感染的治疗或预防使用。
• PROCESS FOR PREPARING PYRANO - [2,3-C]PYRIDINE DERIVITAVES
  申请人：Sisko Joseph

  公开号：US20130116436A1

  公开（公告）日：2013-05-09

  The present invention relates to a process comprising the step of dehydrating a compound of Formula (I): with a suitable dehydrating reagent to form a compound of Formula (II): wherein R 1 -R 7 are as defined herein. Compounds of Formula (II) have shown promise as intermediates to compounds useful for treating bacterial infections.

  本发明涉及一种过程，包括将式(I)化合物与适当的脱水试剂脱水，形成式(II)化合物：其中R1-R7如本文所定义。式(II)化合物已经显示出作为中间体的潜力，用于制备治疗细菌感染的化合物。
• INHIBITORS OF HEPATITIS C VIRUS
  申请人：Bristol-Myers Squibb Co.

  公开号：EP1455809A2

  公开（公告）日：2004-09-15
• NEW THIO DERIVATIVES BEARING LACTAMS AS POTENT HDAC INHIBITORS AND THEIR USES AS MEDICAMENTS
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP2758371B1

  公开（公告）日：2016-06-15