5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde | 742100-39-6

• 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: 5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde
• 英文别名: 5-bromo-2-(2,5-dihydropyrrol-1-yl)benzaldehyde
• CAS: 742100-39-6
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: VFDUPHVXMJXYSH-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±42.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以80%的产率得到5-bromo-2-(1H-pyrrol-1-yl)phenylmethanol
  参考文献：
  名称：

  用于合成分子内氧化还原反应ñ -芳基吡咯由路易斯酸催化的†

  摘要：

  通过路易斯酸介导的1，5-氢化物转移和2-（3-吡咯啉-1-基）芳基醛的异构化来合成N-芳基吡咯的有效方法已经达到了高达89％的收率。该方法学适用于作为电子给体（D）/受体（A）分子的芴衍生物的合成。

  DOI：

  10.1039/c4ob02009j
• 作为产物：
  描述：

  3-吡咯啉 、 5-溴-2-氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde
  参考文献：
  名称：

  用于合成分子内氧化还原反应ñ -芳基吡咯由路易斯酸催化的†

  摘要：

  通过路易斯酸介导的1，5-氢化物转移和2-（3-吡咯啉-1-基）芳基醛的异构化来合成N-芳基吡咯的有效方法已经达到了高达89％的收率。该方法学适用于作为电子给体（D）/受体（A）分子的芴衍生物的合成。

  DOI：

  10.1039/c4ob02009j

文献信息

• Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction
  作者：Chun-Huan Jiang、Xiantao Lei、Le Zhen、Hong-Jin Du、Xiaoan Wen、Qing-Long Xu、Hongbin Sun

  DOI：10.3762/bjoc.10.306

  日期：——

  Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolcular [1,5]-hydride shift/isomerization reaction has been realized, using the inherent reducing power of 3-pyrrolines. A series of N-arylpyrrole containing amines are obtained in high yields.

  利用3-吡咯啉固有的还原能力，通过分子内[1,5]-氢化物转移/异构化反应实现了路易斯酸催化的2-（3-吡咯啉-1-基）苯甲醛的氧化还原中性胺化反应。以高收率获得了一系列含N-芳基吡咯的胺。
• ACRYLAMIDE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1593673A1

  公开（公告）日：2005-11-09

  A compound represented by the formula: wherein R1 is a 5- or 6-membered ring; R3 is a hydrogen atom, a lower alkyl group or a lower alkoxy group; R7 and R8 are each a hydrogen atom or a lower alkyl group; Z1 is another 5- or 6-membered aromatic ring; Z2 is a group represented by -Z2a-W1-Z2b- [wherein Z2a and Z2b are each O, S(O)m (wherein m is 0, 1 or 2), an imino group or a bond, and W1 is an alkylene chain]; X is CR (wherein R is a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acyl group, or R and adjacent R4 may form a 5- or 6-membered alicyclic heterocyclic group) or N; R4 is NR5R6 (wherein R5 and R6 are each a hydrogen atom, a hydrocarbon group, a heterocyclic group or an acyl group), or R5 and R6 are bonded to each other to form a heterocyclic group of NR5R6; and R2 is (1) an amino group which may be a quaternary ammonium or oxide, (2) a nitrogen-containing heterocyclic group which may contain a sulfur atom or an oxygen atom as the ring-constituting atom, in which the nitrogen atom may be converted to a quaternary ammonium or an oxide, or the like; or a salt thereof. The compound has excellent CCR5 antagonistic activity and thus is useful as a prophylactic and/or therapeutic medicine for HIV infection into human peripheral blood monocyte, especially for AIDS.

  一种化合物，其化学式表示为：其中R1是一个5-或6-成员环；R3是氢原子、较低的烷基或较低的烷氧基；R7和R8分别是氢原子或较低的烷基；Z1是另一个5-或6-成员芳香环；Z2是一个由-Z2a-W1-Z2b-表示的基团[其中Z2a和Z2b分别是O、S(O)m（其中m为0、1或2）、亚胺基或键，W1是一个烷基链]；X是CR（其中R是氢原子、较低的烷基、较低的烷氧基、酰基，或R和相邻的R4可能形成5-或6-成员脂环杂环基）或N；R4是NR5R6（其中R5和R6分别是氢原子、烃基、杂环基或酰基），或R5和R6相互连接形成NR5R6的杂环基；R2是（1）可能是季铵盐或氧化物的氨基团，（2）可能包含硫原子或氧原子作为构成环的原子的含氮杂环基，其中氮原子可以转化为季铵盐或氧化物，或类似物；或其盐。该化合物具有出色的CCR5拮抗活性，因此可用作预防和/或治疗HIV感染进入人类外周血单核细胞，特别是艾滋病的药物。
• Dearomatization of Indole Derivatives<i>via</i>Palladium-Catalyzed CH Bond Functionalization of Pyrroles: Convenient Construction of Spiroindolenines
  作者：Xiantao Lei、Hong-Yan Xie、Chang Xu、Xiaoyu Liu、Xiaoan Wen、Hongbin Sun、Qing-Long Xu

  DOI：10.1002/adsc.201600135

  日期：2016.6.16

  An intramolecular palladium(II)‐catalyzed dearomative arylation reaction of indoles via CH bond functionalization was developed, providing access to structurally novel spiroindolenines with moderate to good yields. A one‐pot process for the synthesis of spiroindoline derivatives was also realized.

  分子内钯（II）催化的吲哚的dearomative芳基化反应通过Ç  H键的官能化的开发，提供对结构新颖的spiroindolenines中度至良好的产率。还实现了螺锅二氢吲哚衍生物的一锅法合成。
• Acrylamide derivative, process for producing the same, and use
  申请人：Shiraishi Mitsuru

  公开号：US20060160864A1

  公开（公告）日：2006-07-20

  A compound represented by the formula: wherein R 1 is a 5- or 6-membered ring; R 3 is a hydrogen atom, a lower alkyl group or a lower alkoxy group; R 7 and R 8 are each a hydrogen atom or a lower alkyl group; Z 1 is another 5- or 6-membered aromatic ring; Z 2 is a group represented by -Z 2a -W 1 -Z 2b - [wherein Z 2a and Z 2b are each O, S(O) m (wherein m is 0, 1 or 2), an imino group or a bond, and W 1 is an alkylene chain]; X is CR (wherein R is a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acyl group, or R and adjacent R 4 may form a 5- or 6-membered alicyclic heterocyclic group) or N; R 4 is NR 5 R 6 (wherein R 5 and R 6 are each a hydrogen atom, a hydrocarbon group, a heterocyclic group or an acyl group), or R 5 and R 6 are bonded to each other to form a heterocyclic group of NR 5 R 6 ; and R 2 is (1) an amino group which may be a quaternary ammonium or oxide, (2) a nitrogen-containing heterocyclic group which may contain a sulfur atom or an oxygen atom as the ring-constituting atom, in which the nitrogen atom may be converted to a quaternary ammonium or an oxide, or the like; or a salt thereof. The compound has excellent CCR5 antagonistic activity and thus is useful as a prophylactic and/or therapeutic medicine for HIV infection into human peripheral blood monocyte, especially for AIDS.

  该化合物的化学式为：其中R1是一个5-或6-成员环；R3是氢原子，低烷基或低烷氧基；R7和R8分别是氢原子或低烷基；Z1是另一个5-或6-成员芳香环；Z2是一个由-Z2a-W1-Z2b-表示的基团[其中Z2a和Z2b分别是O，S（O）m（其中m为0，1或2），亚胺基或键，W1是一个烷基链]；X为CR（其中R为氢原子，低烷基，低烷氧基，酰基或R和相邻的R4可能形成一个5-或6-成员脂环杂环基）或N；R4为NR5R6（其中R5和R6分别是氢原子，碳氢基团，杂环基或酰基），或R5和R6连接在一起形成一个NR5R6的杂环基；R2是（1）可能是季铵盐或氧化物的氨基基团，（2）可能包含硫原子或氧原子作为环构成原子的含氮杂环基团，在该基团中，氮原子可以转化为季铵盐或氧化物，或类似物；或其盐。该化合物具有优异的CCR5拮抗活性，因此可用作预防和/或治疗人外周血单核细胞HIV感染，特别是艾滋病的药物。
• Approach to N-aryl pyrroles via diphenyl phosphate-catalyzed [1,5]-Hydride shift/isomerization reaction with indoles
  作者：Xiantao Lei、Hong-Yan Xie、Si-Yuan Chen、Kai-Shun Teng、Xiaoan Wen、Qing-Long Xu、Hongbin Sun

  DOI：10.1016/j.tet.2015.04.112

  日期：2015.6

  A general method to synthesize N-aryl pyrrole derivatives was realized via the reactions of 2-(3-pyrroline-1-yl)arylaldehydes with indoles under acidic conditions, which underwent [1,5]-hydride shift/isomerization process. The desired products could be obtained in good to high yields with a wide substrate scope. (C) 2015 Elsevier Ltd. All rights reserved.