1-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole | 870845-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole
• 英文别名: 1-(4-fluorophenyl)-2,5-dihydropyrrole
• CAS: 870845-82-2
• 化学式: C₁₀H₁₀FN
• 分子量: 163.195
• InChiKey: BWHVGBLJWXVPRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole 在 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(4-氟苯基)吡咯
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081
• 作为产物：
  描述：

  N,N-diallyl-4-fluoroaniline 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  通过过渡金属催化制备N-芳基和N-烷基吡咯啉 的原子有效途径†

  摘要：

  已经开发了由烯丙醇和胺合成N-芳基，N-甲苯磺酰基和N-烷基吡咯啉的方法。反应序列包括钯催化的烯丙基化步骤，其中使用未处理的烯丙醇以良好至极佳的产率生成二烯丙基化的胺。过量烯丙醇对于胺的有效二烯丙基化是必需的，其中过量的醇可以循环三次。对于芳基和甲苯基胺，使用Pd [P（OPh）3 ] 4；对于苄基和烷基胺，使用包含Pd（OAc）2，P n Bu 3和BEt 3的催化体系。胺的电子性质和空间影响都影响烯丙基化的效率。通过（H 2 IMes）（PCy 3）Cl 2 RuCHPh催化的闭环复分解，将分离出的二烯丙基化胺转化为它们相应的吡咯啉，收率良好。开发了一个一锅反应，其中苯胺将其转化为相应的吡咯啉，而无需分离二烯丙基化的中间体。此一锅法反应已成功放大至1 mL苯胺其中分离出N-苯基吡咯啉的产率为95％。证明了分两步制备3-甲基-1-苯基吡咯啉的反应的通用性。

  DOI：

  10.1039/c0ob00383b

文献信息

• Synthesis of Pyrrole Derivatives from Diallylamines by One-Pot Tandem Ring-Closing Metathesis and Metal-Catalyzed Oxidative Dehydrogenation
  作者：Weiqiang Chen、Jianhui Wang

  DOI：10.1021/om400046r

  日期：2013.3.25

  A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles

  在O 2存在下，通过钌卡宾催化的闭环复分解反应和FeCl 3 ·6H 2 O或CuCl 2 ·2H 2 O催化的原位氧化脱氢反应，由二烯丙基胺合成了一系列芳基取代的吡咯衍生物。反应温和，简单，方便。在拟议的催化体系中，氧气气氛对于获得高取代的吡咯转化率起着至关重要的作用。
• Cinnamide compound
  申请人：Kimura Teiji

  公开号：US20060004013A1

  公开（公告）日：2006-01-05

  The present invention relates to a compound represented by Formula (I): (wherein Ar 1 represents an imidazolyl group which may be substituted with 1 to 3 substituents; Ar 2 represents a pyridinyl group, a pyrimidinyl group, or a phenyl group which may be substituted with 1 to 3 substituents; X 1 represents (1) —C≡C— or (2) a double bond etc. which may be substituted; R 1 and R 2 represent, for example, a C1-6 alkyl group or C3-8 cycloalkyl group which may be substituted) or a pharmacologically acceptable salt thereof and to the use thereof as pharmaceutical agents. The object of the present invention is to find a therapeutic or preventive agent for diseases caused by Aβ. According to the present invention, a therapeutic or preventive agents for diseases caused by Aβ can be provided.

  本发明涉及一种由式（I）表示的化合物：（其中Ar1代表可以被1到3个取代基取代的咪唑基团；Ar2代表可以被1到3个取代基取代的吡啶基团、嘧啶基团或苯基；X1代表（1）-C≡C-或（2）可以被取代的双键等；R1和R2代表，例如，可以被取代的C1-6烷基或C3-8环烷基等）或其药理学上可接受的盐，并且用作药物剂。本发明的目的是寻找一种治疗或预防由Aβ引起的疾病的药剂。根据本发明，可以提供治疗或预防由Aβ引起的疾病的药剂。
• Cinnamide Compound
  申请人：Kimura Teiji

  公开号：US20080070902A1

  公开（公告）日：2008-03-20

  The present invention relates to a compound represented by Formula (I): (wherein Ar 1 represents an imidazolyl group which may be substituted with 1 to 3 substituents; Ar 2 represents a pyridinyl group, a pyrimidinyl group, or a phenyl group which may be substituted with 1 to 3 substituents; X 1 represents (1) —C≡C— or (2) a double bond etc. which may be substituted; R 1 and R 2 represent, for example, a C1-6 alkyl group or C3-8 cycloalkyl group which may be substituted) or a pharmacologically acceptable salt thereof and to the use thereof as pharmaceutical agents.

  本发明涉及一种由公式(I)表示的化合物：（其中Ar1代表一个咪唑基，可以用1到3个取代基取代；Ar2代表一个吡啶基，嘧啶基或苯基，可以用1到3个取代基取代；X1代表（1）-C≡C-或（2）一个双键等，可以用取代基取代；R1和R2代表例如C1-6烷基或C3-8环烷基，可以用取代基取代）或其药学上可接受的盐，并用作制药剂。
• CINNAMIDE COMPOUND
  申请人：KIMURA Teiji

  公开号：US20090281310A1

  公开（公告）日：2009-11-12

  The present invention relates to a process for preparing a compound of formula (6a): wherein Ar 1 represents an imidazolyl group which may be substituted with 1 to 3 substituents shown below; Ar 2 represents a pyridinyl group, a pyrimidinyl group or a phenyl group which may be substituted with 1 to 3 substituents; and R 11 represents a group selected from certain substituents.

  本发明涉及一种制备式（6a）化合物的方法，其中Ar1代表一种咪唑基团，该基团可能被下列1至3个取代基取代；Ar2代表一种吡啶基团、嘧啶基团或苯基团，该基团可能被下列1至3个取代基取代；R11代表从某些取代基中选择的一种基团。
• COMPOUND
  申请人：KIMURA Teiji

  公开号：US20110086860A1

  公开（公告）日：2011-04-14

  A compound represented by Formula (I) is provided: wherein Ar 1 represents an imidazolyl group which may be substituted with 1 to 3 substituents; Ar 2 represents a phenyl group which may be substituted with 1 to 3 substituents; X 1 represents (1) —C≡C— or (2) a double bond etc., which may be substituted; R 1 and R 2 represent, for example, a C1-6 alkyl group which may be substituted, or a pharmacologically acceptable salt thereof and to the use thereof as pharmaceutical agents.

  提供一种由式（I）表示的化合物： 其中Ar1代表一种咪唑基团，该基团可以被1到3个取代基取代；Ar2代表一种苯基团，该基团可以被1到3个取代基取代；X1代表（1）—C≡C—或（2）一个双键等，该双键可以被取代；R1和R2代表例如可以被取代的C1-6烷基或其药物学上可接受的盐，以及其作为制药剂的用途。