methyl 4-cyanomethylpyrrole-2-carboxylate | 1158716-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-cyanomethylpyrrole-2-carboxylate
• 英文别名: methyl 4-(cyanomethyl)-1H-pyrrole-2-carboxylate
• CAS: 1158716-14-3
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: SZZYLQREXWSJEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 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：
  65.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 methyl 4-cyanomethylpyrrole-2-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Pyrrole[2,3-d]azepino compounds as agonists of the farnesoid X receptor (FXR)

  摘要：

  Pyrrole[2,3-d]azepines have been identified as potent agonists of the farnesoid X receptor (FXR). Based on the planar X-ray crystal structure of WAY-362450 1 in the ligand binding domain and molecular modeling studies, non-planar reduced compounds were designed which led to agonists that exhibit high aqueous solubility and retain moderate in vitro potency. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.148
• 作为产物：
  描述：

  methyl (2S,4E)-4-cyanomethylene-1-p-toluenesulfonylpyrrolidine-2-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以99%的产率得到methyl 4-cyanomethylpyrrole-2-carboxylate
  参考文献：
  名称：

  Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters

  摘要：

  4-氧代脯氨酸酯的格氏反应、维蒂希反应、特贝反应、霍纳-埃蒙斯反应和 Reformatsky 反应分别产生了相应的 4-酰化或 4-亚烷基化产物。这些产物经碱适当处理后会发生芳香化反应，产生 4-取代的吡咯-2-羧酸酯，如 4-甲基吡咯-2-羧酸甲酯，这是 Atta texana 的一种踪迹信息素。

  DOI：

  10.1248/cpb.57.167

文献信息

• 1,4,5,6-TETRAHYDRO -PYRROLO[2,3-d]AZEPINES AND -IMIDAZO[4,5-d]AZEPINES AS MODULATORS OF NUCLEAR RECEPTOR ACTIVITY
  申请人：Mehlmann John Francis

  公开号：US20090137554A1

  公开（公告）日：2009-05-28

  Disclosed are chemical entities including compounds of Formula I and pharmaceutically acceptable salts thereof, wherein X is chosen from CN, CF 3 , CF 2 H, S(O) n R 8 , and S(O) 2 N(R 9 )R 10 ; Y is chosen from CR 11 and N; Z is chosen from O and NH; R 3 is chosen from —C(O)R 12 and —C(O)N(R 9 )R 10 ; and n, R 1 , R 2 and R 4 -R 12 are defined herein; compositions comprising one or more such chemical entities; and methods of using one or more such chemical entities for modulating the activity of certain receptors (e.g., farnesoid X) or for the treatment or prevention of one or more symptoms of disease or disorder related to the activity of those receptors.

  本发明涉及化学实体，包括式I的化合物及其药学上可接受的盐，其中X选择自CN、CF3、CF2H、S(O)nR8和S(O)2N(R9)R10；Y选择自CR11和N；Z选择自O和NH；R3选择自—C(O)R12和—C(O)N(R9)R10；n、R1、R2和R4-R12在此定义；包含一种或多种此类化学实体的组合物；以及使用一种或多种此类化学实体调节某些受体（例如法尼索德X）的活性或治疗或预防与这些受体活性相关的一种或多种疾病或症状的方法。
• Pyrrole[2,3-d]azepino compounds as agonists of the farnesoid X receptor (FXR)
  作者：John F. Mehlmann、Matthew L. Crawley、Joseph T. Lundquist、Ray J. Unwalla、Douglas C. Harnish、Mark J. Evans、Callain Y. Kim、Jay E. Wrobel、Paige E. Mahaney

  DOI：10.1016/j.bmcl.2009.07.148

  日期：2009.9

  Pyrrole[2,3-d]azepines have been identified as potent agonists of the farnesoid X receptor (FXR). Based on the planar X-ray crystal structure of WAY-362450 1 in the ligand binding domain and molecular modeling studies, non-planar reduced compounds were designed which led to agonists that exhibit high aqueous solubility and retain moderate in vitro potency. (C) 2009 Elsevier Ltd. All rights reserved.
• Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters
  作者：Yasushi Arakawa、Naomi Yagi、Yukimi Arakawa、Ken-ichi Tanaka、Shigeyuki Yoshifuji

  DOI：10.1248/cpb.57.167

  日期：——

  The Grignard, Wittig, Tebbe, Horner–Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.

  4-氧代脯氨酸酯的格氏反应、维蒂希反应、特贝反应、霍纳-埃蒙斯反应和 Reformatsky 反应分别产生了相应的 4-酰化或 4-亚烷基化产物。这些产物经碱适当处理后会发生芳香化反应，产生 4-取代的吡咯-2-羧酸酯，如 4-甲基吡咯-2-羧酸甲酯，这是 Atta texana 的一种踪迹信息素。