ethyl 2-(tetrahydrothiophen-3-yl)acetate | 150332-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: ethyl 2-(tetrahydrothiophen-3-yl)acetate
• 英文别名: ethyl 2-(thiolan-3-yl)acetate
• CAS: 150332-02-8
• 化学式: C₈H₁₄O₂S
• 分子量: 174.264
• InChiKey: JAPAOTYLWINGNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(tetrahydrothiophen-3-yl)acetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.58h， 以89%的产率得到2-(tetrahydrothiophen-3-yl)ethanol
  参考文献：
  名称：

  通过固相肽合成制备 C 端肽 α-酮酸的一般策略†

  摘要：

  一个新的 氰硫-ylide 为基础的接头使合成 C-末端肽α-酮酸通过固相合成。所需接头的制备及其在各种领域的应用C报道了具有未受保护侧链的末端肽 α-酮酸。

  DOI：

  10.1039/b901198f
• 作为产物：
  描述：

  ethyl 2-(dihydrothiophen-3(2H)-ylidene)acetate 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到ethyl 2-(tetrahydrothiophen-3-yl)acetate
  参考文献：
  名称：

  通过固相肽合成制备 C 端肽 α-酮酸的一般策略†

  摘要：

  一个新的 氰硫-ylide 为基础的接头使合成 C-末端肽α-酮酸通过固相合成。所需接头的制备及其在各种领域的应用C报道了具有未受保护侧链的末端肽 α-酮酸。

  DOI：

  10.1039/b901198f

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015180612A1

  公开（公告）日：2015-12-03

  Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

  揭示了新型视黄醇相关孤儿受体γ（RORγ）调节剂及其在通过RORγ介导的疾病治疗中的应用。
• Potent HIV protease inhibitors: the development of tetrahydrofuranylglycines as novel P2-ligands and pyrazine amides as P3-ligands
  作者：Arun K. Ghosh、Wayne J. Thompson、M. Katharine Holloway、Sean P. McKee、Tien T. Duong、Hee Yoon Lee、Peter M. Munson、Anthony M. Smith、Jenny M. Wai、Paul L. Darke、Joan A. Zugay、Emilio A. Emini、William A. Schleif、Joel R. Huff、Paul S. Anderson

  DOI：10.1021/jm00068a006

  日期：1993.8.1

  A series of protease inhibitors bearing constrained unnatural amino acids at the P2-position and novel heterocycles at the P3-position of compound 1 (Ro 31-8959) were synthesized, and their in vitro enzyme inhibitory and antiviral activities were evaluated. Replacement of P2-asparagine of compound 1 with (2S,3'R)-tetrahydrofuranylglycine resulted in improvement in enzyme inhibitory as well as antiviral potencies (compound 23). Interestingly, incorporation of (2S,3'S)-tetrahydrofuranylglycine at the P2-position proved to be less effective. The resulting compound 24 was 100-fold less potent than the 2S,3R-isomer (compound 23). This stereochemical preference indicated a hydrogen-bonding interaction between the tetrahydrofuranyl oxygen and the residues of the S2-region of the enzyme active site. Furthermore, replacement of P3-quinolinoyl ligand of 1 with various novel heterocycles resulted in potent inhibitors of HIV proteases. Of particular interest, compound 2 with (2S,3'R)-tetrahydrofuranylglycine at P2 and pyrazine derivative at P3 is one of the most potent inhibitors of HIV-1 (IC50 value 0.07 nM) and HIV-2 (IC50 value 0.18 nM) proteases. Another important result in this series is the identification of compound 27 in which the P2-P3-amide carbonyl has been removed. The resulting compound 27 has exhibited improvement in antiviral potency while retaining the enzyme inhibitory potency similar to compound 1.
• PIPERAZINE DERIVATIVES AS ROR-GAMMA MODULATORS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3148975B1

  公开（公告）日：2018-11-28
• NOVEL COMPOUNDS
  申请人：GlaxoSmithKline Intellectual Property Developement Limited

  公开号：US20170197978A1

  公开（公告）日：2017-07-13

  The present invention relates to novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
• US9902735B2
  申请人：——

  公开号：US9902735B2

  公开（公告）日：2018-02-27