2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one | 1542131-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one
• 英文别名: 2-(1H-Benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one；2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-one
• CAS: 1542131-26-9
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: FUYHSYWFKAPTKX-UHFFFAOYSA-N

物化性质

• 沸点：
  493.2±40.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以33.333%的产率得到
  参考文献：
  名称：

  Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution

  摘要：

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.

  DOI：

  10.1021/ol403630g
• 作为产物：
  描述：

  4-甲氧基吡啶 在 盐酸 、 水 、 lithium tri-t-butoxyaluminum hydride 、 copper(I) bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 乙基苯 为溶剂， 反应 11.84h， 生成 2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution

  摘要：

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.

  DOI：

  10.1021/ol403630g

文献信息

• Development of a Concise, Asymmetric Synthesis of a Smoothened Receptor (SMO) Inhibitor: Enzymatic Transamination of a 4-Piperidinone with Dynamic Kinetic Resolution
  作者：Zhihui Peng、John W. Wong、Eric C. Hansen、Angela L. A. Puchlopek-Dermenci、Hugh J. Clarke

  DOI：10.1021/ol403630g

  日期：2014.2.7

  A concise, asymmetric synthesis of a smoothened receptor inhibitor (1) is described. The synthesis features an enzymatic transamination with concurrent dynamic kinetic resolution (DKR) of a 4-piperidone (4). to establish the two stereogenic centers required in a single step. This efficient reaction affords the desired anti amine (3) in >10:1 dr and >99% ee. The title compound is prepared in only five steps with 40% overall yield.