(1,5-dimethyl-1H-indol-3-yl)acetonitrile | 176688-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1,5-dimethyl-1H-indol-3-yl)acetonitrile
• 英文别名: 2-(1,5-Dimethylindol-3-yl)acetonitrile
• CAS: 176688-97-4
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: XQBZSWANOXKPQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1,5-dimethyl-1H-indol-3-yl)acetonitrile 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 C-[1-(1,5-Dimethyl-1H-indol-3-yl)-cyclopentyl]-methylamine
  参考文献：
  名称：

  New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships

  摘要：

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.

  DOI：

  10.1016/0223-5234(96)80445-4
• 作为产物：
  描述：

  5-甲基吲哚-3-乙腈 、 碘甲烷 在 sodium hydride 作用下， 以89%的产率得到(1,5-dimethyl-1H-indol-3-yl)acetonitrile
  参考文献：
  名称：

  通过 NMR 光谱、分子建模和 X 射线晶体学对腈取代的螺环丙基羟吲哚的构型异构体进行结构解析

  摘要：

  关键词：核磁共振；1H-核磁共振；13C-核磁共振；螺环吲哚；环丙烷；各向异性；X 射线晶体学；DFT 计算

  DOI：

  10.1002/mrc.4293

文献信息

• Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst
  作者：Xiaojian Jiang、Haitao Wang、Haoquan He、Wei Wang、Yuqiang Wang、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1002/adsc.201801133

  日期：2018.12.21

  An enantioselective fluorination of 3‐functionalized oxindoles using electron‐rich amino urea catalyst is described. Various 3‐functionalized 3‐fluoro‐2‐oxindoles were obtained in good yields and enantio‐selectivity. The resulting enantioenriched 3‐methylene nitrile 3‐fluoro‐2‐oxindole product was found to inhibit indoleamine 2,3‐dioxygenase considerably.

  描述了使用富电子氨基脲催化剂对3-官能化吲哚进行对映选择性氟化的方法。获得了各种3官能化的3-氟-2-氧吲哚，并具有良好的收率和对映选择性。发现所得的对映体富集的3-亚甲基腈3-氟-2-氧吲哚产物可显着抑制吲哚胺2,3-二加氧酶。
• New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships
  作者：R Bellemin、J Decerprit、D Festal

  DOI：10.1016/0223-5234(96)80445-4

  日期：1996.1

  A series of ureas containing the indole group were synthesized and assessed for their ability to inhibit arterial and intestinal ACAT and to lower plasma total cholesterol in a cholesterol-fed rat model. The structural modulations carried out in this series led to compounds which proved to be very active in both the inhibition of aortic ACAT in vitro and the inhibition of rat cholesterol intestinal absorption in vivo. Several compounds from this series exhibit a remarkable hypocholesterolaemic effect with ED(25) less than 0.1 mg/kg po.
• Structure elucidation of configurational isomers of nitrile-substituted spirocyclopropyloxindoles by NMR spectroscopy, molecular modeling, and X-ray crystallography
  作者：J. Benjamín García-Vázquez、Daphne E. González-Juárez、Martha S. Morales-Ríos、Oscar R. Suárez-Castillo、Yolanda Mora-Pérez

  DOI：10.1002/mrc.4293

  日期：2015.12

  Keywords: NMR; 1H-NMR; 13C-NMR; spirooxindoles; cyclopropanes; anisotropy; X-ray crystallography; DFT calculations

  关键词：核磁共振；1H-核磁共振；13C-核磁共振；螺环吲哚；环丙烷；各向异性；X 射线晶体学；DFT 计算