1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-one | 1181225-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-one
• CAS: 1181225-30-8；1032917-35-3
• 化学式: C₂₃H₁₈BrNO
• 分子量: 404.306
• InChiKey: HZXGPCSMGXURBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-one 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  用于合成[小α]和[小δ]咔啉衍生物的区域选择性转换方法

  摘要：

  报道了从常见的吲哚基查耳酮肟酯前体开始的用于访问小α和小δ-咔啉衍生物的无金属方案。该反应涉及温和条件，并使用区域发散性方法...。

  DOI：

  10.1039/c6cc09468f
• 作为产物：
  描述：

  苯甲醛 在 四溴化碳 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 1.67h， 生成 1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-one
  参考文献：
  名称：

  可见光诱导卤素键辅助吲哚和查耳酮的傅克反应

  摘要：

   利益冲突 没有需要声明的冲突。

  DOI：

  10.1002/adsc.202400255

文献信息

• Synthesis and application of modified silica sulfuric acid as a solid acid heterogeneous catalyst in Michael addition reactions
  作者：Mohammad Ali Zolfigol、Hojat Veisi、Farajollah Mohanazadeh、Alireza Sedrpoushan

  DOI：10.1002/jhet.659

  日期：2011.7

  Modified silica sulfuric acid (MSSA) as a new type of silica sulfuric acid was prepared and effectively used in the conjugate addition of indole, pyrrole, and thiols with Michael acceptors under mild conditions at room temperature. Also, MSSA was used as a catalyst for the synthesis of 1,1,3‐tri‐indolyl compounds in good to excellent yield at room temperature. J. Heterocyclic Chem., (2011).

  制备了新型的二氧化硅硫酸改性的二氧化硅硫酸（MSSA），并在室温下于温和条件下有效地用于吲哚，吡咯和硫醇与迈克尔受体的共轭加成中。此外，MSSA还用作催化剂，可在室温下以良好至极好的收率合成1,1,3-三-吲哚基化合物。J.杂环化​​学。（2011）。
• Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as new reagents for conjugate addition of indole, pyrrole with α,β-unsaturated ketones
  作者：R. Ghorbani-Vaghei、S. Hajinazari、M. Engashte

  DOI：10.1007/s13738-012-0087-2

  日期：2012.10

  Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide[TBBDA] were used as efficient reagents for conjugate addition of indole and pyrrole with α,β-unsaturated ketones and also, double-conjugate 1,4-addition of indoles to dibenzylidenacetones.

  聚（N，N'-二溴-N-乙基苯-1,3-二磺酰胺）[PBBS]和N，N，N'，N'-四溴苯-1,3-二磺酰胺[TBBDA]用作有效试剂用于吲哚和吡咯与α，β-不饱和酮的共轭加成，以及吲哚与二亚苄基丙酮的双共轭1，4-加成。
• Chiral Phosphoric Acid Catalyzed Asymmetric Friedel–Crafts Alkylation of Indoles with Simple α,β-Unsaturated Aromatic Ketones
  作者：Hong-Ying Tang、Ai-Dang Lu、Zheng-Hong Zhou、Guo-Feng Zhao、Lian-Nian He、Chu-Chi Tang

  DOI：10.1002/ejoc.200700980

  日期：2008.3

  Asymmetric Michael-type Friedel–Crafts (F-C) alkylations of indoles with nonchelating α,β-unsaturated aromatic ketones catalyzed by a chiral H8-BINOL-based phosphoric acid were investigated. The reactions took place smoothly in the presence of only 2 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.(© Wiley-VCH

  研究了由基于手性 H8-BINOL 的磷酸催化的吲哚与非螯合 α,β-不饱和芳族酮的不对称迈克尔型 Friedel-Crafts (FC) 烷基化反应。反应在室温下仅 2 mol% 的催化剂存在下顺利进行，以良好的收率和适度的对映选择性提供所需的 FC 烷基化产物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2008)
• Catalytic conjugate addition of indole to α,β-unsaturated ketones by Co(ClO4)2·6H2O/bis-Schiff base complexes
  作者：Yong Hai Hui、Chun Mei Chen、Zheng Feng Xie

  DOI：10.1016/j.cclet.2012.03.015

  日期：2012.5

  Co(ClO4)2·6H2O/bis-Schiff base complexes promoted the conjugate addition of indole to α,β-unsaturated ketones under mild conditions, giving the corresponding addition products with high yields. And the complex has been characterized with XRD and IR.

  Co（ClO 4）2 ·6H 2 O /双-席夫碱配合物在温和条件下促进了吲哚向α，β-不饱和酮的共轭加成反应，从而以高收率得到了相应的加成产物。并用XRD和IR对复合物进行了表征。
• Al-MCM-41 as a mild and ecofriendly catalyst for Michael addition of indole to α,β-unsaturated ketones
  作者：Thirumeni Subramanian、Mayilvasagam Kumarraja、Kasi Pitchumani

  DOI：10.1016/j.molcata.2012.05.024

  日期：2012.11

  Mesoporous Al-MCM-41 catalyzes the chemoselective Michael addition reaction between indoles and alpha,beta-unsaturated ketones to afford beta-indolylketones at room temperature with excellent yields. The higher catalytic activity is attributed to Lewis acidic Al and the large surface area. The catalyst is readily recovered and reused more than six times without loss in its catalytic activity. The substitution at the indole nucleus occurs exclusively at the 3-position and N-alkylation products are not observed. (C) 2012 Elsevier B.V. All rights reserved.