1-(5-isobutylthiophen-2-yl)ethanone | 84702-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-isobutylthiophen-2-yl)ethanone
• 英文别名: 1-(5-isobutyl-[2]thienyl)-ethanone；1-(5-Isobutyl-[2]thienyl)-aethanon；1-[5-(2-Methylpropyl)thiophen-2-yl]ethan-1-one；1-[5-(2-methylpropyl)thiophen-2-yl]ethanone
• CAS: 84702-96-5
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: OARPIKYRAJLSCE-UHFFFAOYSA-N

物化性质

• 沸点：
  131-133 °C(Press: 0.5 Torr)
• 密度：
  1.0317 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-isobutylthiophen-2-yl)ethanone 在 盐酸 、 4,4-二甲基-2-环己基-1-酮 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 异丙醇 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 反应 6.67h， 生成 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-isobutyl-thiophen-2-yl)-propan-1-one
  参考文献：
  名称：

  Novel S1P₁ Receptor Agonists - Part 2: From Bicyclo[3.1.0]hexane-Fused Thiophenes to Isobutyl Substituted Thiophenes

  摘要：

  Previously, we reported on the discovery of a novel series of bicyclo[3.1.0]hexane fused thiophene derivatives that serve as potent and selective S1P(1), receptor agonists. Here, we discuss our efforts to simplify the bicyclohexane fused thiophene head. In a first step the bicyclohexane moiety could be replaced by a simpler, less rigid cyclohexane ring without compromising the SIP receptor affinity profile of these novel compounds. In a second step, the thiophene head was simplified even further by replacing the cyclohexane ring with an isobutyl group attached either to position 4 or position S of the thiophene. These structurally much simpler headgroups again furnished potent and selective S1P(1) agonists (e.g., 87), which efficiently and dose dependently reduced the number of circulating lymphocytes upon oral administration to male Wistar rats. For several compounds discussed in this report lymphatic transport is an important route of absorption that may offer opportunities for a tissue targeted approach with minimal plasma exposure.

  DOI：

  10.1021/jm401456d
• 作为产物：
  描述：

  2-甲基-1-噻吩-2-丙烷-1-酮 在 氢氧化钾 、 磷酸 、 一水合肼 、 乙二醇 作用下， 生成 1-(5-isobutylthiophen-2-yl)ethanone
  参考文献：
  名称：

  Profft, Chemiker-Zeitung, Chemische Apparatur, 1958, vol. 82, p. 295,297

  摘要：

  DOI：

文献信息

• Thiophene derivatives as S1P1/EDGE1 receptor agonists
  申请人：Bolli Martin

  公开号：US20100048648A1

  公开（公告）日：2010-02-25

  The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.

  这项发明涉及新型噻吩衍生物，其制备以及作为药用活性化合物的用途。所述化合物特别作为免疫调节剂。
• Gol'dfarb et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3636,3639; engl. Ausg. S. 3596, 3598
  作者：Gol'dfarb et al.

  DOI：——

  日期：——
• WO2008/29306
  申请人：——

  公开号：——

  公开（公告）日：——
• THIOPHENE DERIVATIVES AS S1P1/EDG1 RECEPTOR AGONISTS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP2069322A2

  公开（公告）日：2009-06-17
• US8133910B2
  申请人：——

  公开号：US8133910B2

  公开（公告）日：2012-03-13