3-benzoyl-2-cyanobutyronitrile | 312307-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2-cyanobutyronitrile
• 英文别名: (1-methyl-2-oxo-2-phenylethyl)propanedinitrile；Propanedinitrile, (1-methyl-2-oxo-2-phenylethyl)-；2-(1-oxo-1-phenylpropan-2-yl)propanedinitrile
• CAS: 312307-14-5
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: MFDOMAUESJOOMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2-cyanobutyronitrile 在 三氟乙酸 作用下， 反应 1.0h， 以77%的产率得到2-氨基-4-甲基-5-苯基呋喃-3-腈
  参考文献：
  名称：

  Acid-mediated Cyclization of 3-Benzoyl-2-cyanobutyronitrile to 2-Amino-4-methyl-5-phenylfuran-3-carbonitrile

  摘要：

  Cyclization of 3-benzoyl-2-cyanobutyronitrile to 2-amino-4-methyl-5-phenylfuran-3-carbonitrile was effected under acidic conditions, rather than the basic conditions previously reported. Since treatment with trifluoroacetic acid (TFA) at room temperature is very mild, 2-amino-4-methyl-5-phenylfuran-3-carbonitriles containing various functional groups can be accessed via this route.

  DOI：

  10.3987/com-03-s(p)13
• 作为产物：
  描述：

  苯丙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 3-benzoyl-2-cyanobutyronitrile
  参考文献：
  名称：

  Acid-mediated Cyclization of 3-Benzoyl-2-cyanobutyronitrile to 2-Amino-4-methyl-5-phenylfuran-3-carbonitrile

  摘要：

  Cyclization of 3-benzoyl-2-cyanobutyronitrile to 2-amino-4-methyl-5-phenylfuran-3-carbonitrile was effected under acidic conditions, rather than the basic conditions previously reported. Since treatment with trifluoroacetic acid (TFA) at room temperature is very mild, 2-amino-4-methyl-5-phenylfuran-3-carbonitriles containing various functional groups can be accessed via this route.

  DOI：

  10.3987/com-03-s(p)13

文献信息

• PROCESS FOR PRODUCING PYRROLE COMPOUND
  申请人：Ikemoto Tomomi

  公开号：US20110306769A1

  公开（公告）日：2011-12-15

  The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

  本发明提供了一种作为药物产品有用的磺酰吡咯化合物的生产方法，一种用于该方法的中间体的生产方法，以及一种新的中间体。本发明涉及一种生产磺酰吡咯化合物（VIII）的方法，包括还原化合物（III）并水解还原产物以得到化合物（IV），将化合物（IV）经过磺酰化反应得到化合物（VI），并将化合物（VI）经过胺化反应。
• An Efficient, Scalable and Eco‐friendly Synthesis of 4,5‐substituted Pyrrole‐3‐Carbonitriles by Intramolecular Annulation on Pd/C and HZSM‐5
  作者：Jianchao Chen、Chengtao Li、Yanan Zhou、Changshan Sun、Tiemin Sun

  DOI：10.1002/cctc.201900154

  日期：2019.4.4

  An efficient and eco‐friendly protocol for the synthesis of diverse 4,5‐substituted 1H‐pyrrole‐3‐carbonitriles has been developed using commercially available HZSM‐5 and Pd/C as recyclable heterogeneous catalysts with more excellent yields (up to 98 %) than traditional liquids acids, and successfully applied in the practical synthesis of vonoprazan. The conspicuous features of this protocol are higher

  使用市售的HZSM-5和Pd / C作为可回收的非均相催化剂，已开发出一种高效且环保的方案，用于合成多种4,5-取代的1H-吡咯-3-腈，具有更高的产率（高达98％） ）比传统的液体酸，并成功地将其实际应用合成了vonoprazan。该协议的显着特征是更高的产品收率，易于加工，生态友好和催化剂的可重复使用性。
• Process for producing pyrrole compound
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2765130A2

  公开（公告）日：2014-08-13

  The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

  本发明提供了一种可用作医药产品的磺酰基吡咯化合物的生产方法、一种用于该方法的中间体的生产方法以及一种新型中间体。 本发明涉及磺酰基吡咯化合物（VIII）的生产方法，其中包括还原化合物（III）并水解还原产物得到化合物（IV），将化合物（IV）进行磺化反应得到化合物（VI），以及将化合物（VI）进行胺化反应。
• Intermediates for use in a process of producing pyrrole compounds
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2765130B1

  公开（公告）日：2017-07-26
• US8822694B2
  申请人：——

  公开号：US8822694B2

  公开（公告）日：2014-09-02