methyl 4-cyclopropyl-1H-pyrrole-2-carboxylate | 1263082-23-0

• 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-cyclopropyl-1H-pyrrole-2-carboxylate
• 英文别名: Methyl 4-cyclopropyl-1H-pyrrole-2-carboxylate
• CAS: 1263082-23-0
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: QTUAIBRPGOPEFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-cyclopropyl-1H-pyrrole-2-carboxylate 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Discovery and evaluation of Ca v 3.2-selective T-type calcium channel blockers

  摘要：

  We identified and characterized a series of pyrrole amides as potent, selective Ca(v)3.2-blockers. This series culminated with the identification of pyrrole amides 13b and 26d, with excellent potencies and/or selectivities toward the Ca(v)3.1- and Ca(v)3.3-channels. These compounds display poor physicochemical and DMPK properties, making their use difficult for in vivo applications. Nevertheless, they are well-suited for in vitro studies. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.062
• 作为产物：
  描述：

  4-碘-1-(甲苯-4-磺酰基)-1H-吡咯-2-羧酸甲酯 在 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 methyl 4-cyclopropyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Discovery and evaluation of Ca v 3.2-selective T-type calcium channel blockers

  摘要：

  We identified and characterized a series of pyrrole amides as potent, selective Ca(v)3.2-blockers. This series culminated with the identification of pyrrole amides 13b and 26d, with excellent potencies and/or selectivities toward the Ca(v)3.1- and Ca(v)3.3-channels. These compounds display poor physicochemical and DMPK properties, making their use difficult for in vivo applications. Nevertheless, they are well-suited for in vitro studies. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.062

文献信息

• Enantioselective Synthesis of <i>N</i>-Benzylic Heterocycles by Ni/Photoredox Dual Catalysis
  作者：Caitlin R. Lacker、Travis J. DeLano、Emily P. Chen、Jongrock Kong、Kevin M. Belyk、Tiffany Piou、Sarah E. Reisman

  DOI：10.1021/jacs.2c07917

  日期：2022.11.9

  trifluoroborates with aryl bromides using Ni/photoredox dual catalysis has been developed. This C(sp2)–C(sp3) cross-coupling provides access to pharmaceutically relevant chiral N-benzylic heterocycles in good to excellent enantioselectivity when bioxazolines (BiOX) are used as the chiral ligand. High-throughput experimentation significantly streamlined reaction development by identifying BiOX ligands for further

  已经开发出使用 Ni/光氧化还原双重催化的 α -N-杂环三氟硼酸盐与芳基溴化物的不对称交叉偶联。当双恶唑啉 (BiOX) 用作手性配体时，这种 C(sp 2 )–C(sp 3 ) 交叉偶联提供了获得药学相关的手性N-苄基杂环的途径，具有良好至优异的对映选择性。高通量实验通过识别 BiOX 配体进行进一步研究以及快速优化新三氟硼酸盐的条件，显着简化了反应开发。
• EP2460794
  申请人：——

  公开号：——

  公开（公告）日：——
• PHARMACEUTICAL COMPOSITION CONTAINING FUSED HETERO-RING DERIVATIVE
  申请人：Tachibana Yuuki

  公开号：US20120277238A1

  公开（公告）日：2012-11-01

  The present invention provides a compound which indicates a histamine H4 receptor modulating activity. A compound represented by a formula (I): wherein A ring is a ring represented by the following formula: wherein R 1 is substituted or unsubstituted alkyl, etc., W is —O—, etc., n is an integer of 0 to 6; X is —N(R 7 )— or —O—; R 7 is hydrogen, substituted or unsubstituted alkyl, etc.; Y is —C(R 8 )═ or —N═; R 8 is hydrogen, substituted or unsubstituted alkyl, etc.; Z is ═O, ═S, etc.; B ring is a ring represented by the following formula: wherein R 10 is each independently substituted or unsubstituted alkyl, halogen, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted amino; R 11 , R 12a and R 12b are each independently hydrogen or substituted or unsubstituted alkyl, etc.; p is an integer of 0 to 4, or its pharmaceutically acceptable salt, or a solvate thereof.
• Discovery and evaluation of Ca v 3.2-selective T-type calcium channel blockers
  作者：Olivier Bezençon、Luboš Remeň、Sylvia Richard、Catherine Roch、Melanie Kessler、Eric A. Ertel、Richard Moon、Jacques Mawet、Thomas Pfeifer、Bruno Capeleto

  DOI：10.1016/j.bmcl.2017.09.062

  日期：2017.12

  We identified and characterized a series of pyrrole amides as potent, selective Ca(v)3.2-blockers. This series culminated with the identification of pyrrole amides 13b and 26d, with excellent potencies and/or selectivities toward the Ca(v)3.1- and Ca(v)3.3-channels. These compounds display poor physicochemical and DMPK properties, making their use difficult for in vivo applications. Nevertheless, they are well-suited for in vitro studies. (C) 2017 Elsevier Ltd. All rights reserved.