(1-methyl-1,2,3,4-tetrahydroquinolin-2-yl)acetonitrile | 957763-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1-methyl-1,2,3,4-tetrahydroquinolin-2-yl)acetonitrile
• CAS: 957763-79-0
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: APAMMBMXTHWRIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1-methyl-1,2,3,4-tetrahydroquinolin-2-yl)acetonitrile 在 盐酸 作用下， 反应 3.0h， 以79%的产率得到(1-methyl-1,2,3,4-tetrahydroquinolin-2-yl)acetic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of tetrahydroquinoline-linked thiazolidinedione derivatives as pparγ selective activators

  摘要：

  A series of tetrahydroquinoline-linked thiazolidinediones was designed and synthesized and their peroxisome proliferator activated receptor-gamma (PPAR gamma) agonistic activities were evaluated. A number of analogs were revealed to have significant PPAR gamma agonistic activity. Among these compounds, compound 1h possessing N-heptyl moiety was found to be the most active in PPAR gamma transactivation assay. Molecular modeling suggested that the heptyl group of 1h appropriately interacts with hydrophobic amino acid residues in the active site of PPAR gamma.

  DOI：

  10.1016/s0385-5414(07)00053-6
• 作为产物：
  描述：

  氰化钠 、 2-iodomethyl-1-methyl-1,2,3,4-tetrahydroquinoline 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以94%的产率得到(1-methyl-1,2,3,4-tetrahydroquinolin-2-yl)acetonitrile
  参考文献：
  名称：

  Design, synthesis, and evaluation of tetrahydroquinoline-linked thiazolidinedione derivatives as pparγ selective activators

  摘要：

  A series of tetrahydroquinoline-linked thiazolidinediones was designed and synthesized and their peroxisome proliferator activated receptor-gamma (PPAR gamma) agonistic activities were evaluated. A number of analogs were revealed to have significant PPAR gamma agonistic activity. Among these compounds, compound 1h possessing N-heptyl moiety was found to be the most active in PPAR gamma transactivation assay. Molecular modeling suggested that the heptyl group of 1h appropriately interacts with hydrophobic amino acid residues in the active site of PPAR gamma.

  DOI：

  10.1016/s0385-5414(07)00053-6

文献信息

• Chemodivergent C(sp3)–H and C(sp2)–H cyanomethylation using engineered carbene transferases
  作者：Juner Zhang、Ailiena O. Maggiolo、Edwin Alfonzo、Runze Mao、Nicholas J. Porter、Nayla M. Abney、Frances H. Arnold

  DOI：10.1038/s41929-022-00908-x

  日期：——

  The ubiquity of C–H bonds presents an opportunity to efficiently elaborate and build complexity in organic molecules. Methods for selective functionalization, however, must differentiate among multiple, chemically similar C–H bonds: enzymes are attractive because they can be finely tuned using directed evolution to achieve divergent reaction outcomes. Here we present engineered enzymes that effect

  C-H 键的普遍存在为有效地阐述和构建有机分子的复杂性提供了机会。然而，选择性功能化的方法必须区分多个化学上相似的 C-H 键：酶之所以有吸引力，是因为它们可以使用定向进化进行微调，以实现不同的反应结果。在这里，我们提出了具有独特选择性的工程酶，可实现全新的 C–H 烷基化（C–H 卡宾插入）：基于细胞色素 P450 的卡宾转移酶将 α-氰基卡宾传递到 α-氨基 C( sp 3 ) -H键或N-取代芳烃的邻位芳烃C( sp 2 )-H键。这两种转化通过不同的机制进行，但只需要对蛋白质支架进行最小的改变来调整酶的化学选择性。 C( sp 3 )–H 烷基酶的结构研究揭示了活性位点螺旋破坏，与天然酶相比，这改变了底物结合袋的结构和静电。总的来说，这项工作展示了使用高度可调的酶作为 C-H 官能化催化剂进行不同分子衍生化的优势。