[3-(1-Aminopropan-2-yl)phenyl]-phenylmethanone | 771573-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-(1-Aminopropan-2-yl)phenyl]-phenylmethanone
• 英文别名: [3-(1-aminopropan-2-yl)phenyl]-phenylmethanone
• CAS: 771573-45-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: GGPQNOXUUQVFEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吲哚-2-羧酸 、 [3-(1-Aminopropan-2-yl)phenyl]-phenylmethanone 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到N-(2-(3-benzoylphenyl)propyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway

  摘要：

  We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, amide conjugates of ketoprofen and indole, showed inhibitory activity and membrane permeability, while also improving the microsome stability. Among them, 33 and 42 inhibited Gli-luciferase reporter in C3H10T1/2 cells that were exogenously transfected with Gli1 with 2.6 mu M and 1.6 mu M of IC50, respectively, and in Rh30 cells that endogenously over-express Gli1, and were selective to Gli1 over Gli2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.001
• 作为产物：
  描述：

  2-(3-苯甲酰基苯基)-丙腈 在 nickel(II) triflate 、 氨 、 氢气 、 双(2-二苯基膦乙基)苯基磷 作用下， 以 2,2,2-三氟乙醇 为溶剂， 120.0 ℃ 、4.0 MPa 条件下， 反应 5.0h， 以70%的产率得到[3-(1-Aminopropan-2-yl)phenyl]-phenylmethanone
  参考文献：
  名称：

  镍催化腈和胺的氢化偶联用于一般胺合成

  摘要：

  合成胺的有效和通用方法在化学工业中仍然有很高的需求。在许多已知的方法中，催化加氢是一种经济有效且经工业验证的反应，目前用于生产多种此类化合物。我们报告了一种均相镍催化剂，用于将一系列芳族、杂芳族和脂肪族腈与伯胺和仲胺或氨进行氢化交叉偶联。该通用氢化方案通过直接和高选择性合成 > 230 种功能化和结构多样的胺（包括药学相关和手性产物）以及15N-同位素标记应用。

  DOI：

  10.1126/science.abn7565

文献信息

• Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway
  作者：Neeraj Mahindroo、Michele C. Connelly、Chandanamali Punchihewa、Lei Yang、Bing Yan、Naoaki Fujii

  DOI：10.1016/j.bmc.2010.05.001

  日期：2010.7

  We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, amide conjugates of ketoprofen and indole, showed inhibitory activity and membrane permeability, while also improving the microsome stability. Among them, 33 and 42 inhibited Gli-luciferase reporter in C3H10T1/2 cells that were exogenously transfected with Gli1 with 2.6 mu M and 1.6 mu M of IC50, respectively, and in Rh30 cells that endogenously over-express Gli1, and were selective to Gli1 over Gli2. (C) 2010 Elsevier Ltd. All rights reserved.
• Nickel-catalyzed hydrogenative coupling of nitriles and amines for general amine synthesis
  作者：Vishwas G. Chandrashekhar、Wolfgang Baumann、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1126/science.abn7565

  日期：2022.6.24

  Efficient and general methods for the synthesis of amines remain in high demand in the chemical industry. Among the many known processes, catalytic hydrogenation is a cost-effective and industrially proven reaction and currently used to produce a wide array of such compounds. We report a homogeneous nickel catalyst for hydrogenative cross coupling of a range of aromatic, heteroaromatic, and aliphatic

  合成胺的有效和通用方法在化学工业中仍然有很高的需求。在许多已知的方法中，催化加氢是一种经济有效且经工业验证的反应，目前用于生产多种此类化合物。我们报告了一种均相镍催化剂，用于将一系列芳族、杂芳族和脂肪族腈与伯胺和仲胺或氨进行氢化交叉偶联。该通用氢化方案通过直接和高选择性合成 > 230 种功能化和结构多样的胺（包括药学相关和手性产物）以及15N-同位素标记应用。