1-(4-bromobenzyl)-5-bromo-1H-indole | 674811-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4-bromobenzyl)-5-bromo-1H-indole
• 英文别名: 5-bromo-1-(4-bromobenzyl)-1H-indole；5-Bromo-1-[(4-bromophenyl)methyl]indole
• CAS: 674811-25-7
• 化学式: C₁₅H₁₁Br₂N
• 分子量: 365.067
• InChiKey: NPKYWERIVMSCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-5-bromo-1H-indole 在 lithium hydroxide monohydrate 、 sodium carbonate 、 ethyl 2-nitrosopropenoate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Indole-Derived Psammaplin A Analogues as Epigenetic Modulators with Multiple Inhibitory Activities

  摘要：

  A SAR study has been carried out around a modified scaffold of the natural product psammaplin A obtained by replacing the o-bromophenol unit by an indole ring. A series of indole psammaplin A constructs were generated in a short synthetic sequence that starts with the functionalization of the C3 indole position with in situ generated nitrosoacrylate, and this is followed by protection of the beta-indole-alpha-oximinoesters, saponification, condensation with symmetrical diamines, and deprotection. Biochemical and cellular characterization using U937 and MCF-7 cells confirmed that many of these analogues displayed more potent actitivies than the parent natural product. Moreover, in addition to the reported HDAC and DNMT dual epigenetic inhibitory profile of the parent compound, some analogues, notably 4a (UVI5008), also inhibited the NAD(+)-dependent SIRT deacetylase enzymes. The SAR study provides structural insights into the mechanism of action of these multiple epigenetic ligands and paves the way for additional structural exploration to optimize their pharmacological profiles. Because of their multi(epi)target features and their action in ex vivo samples, the indole-based psammaplin A derivatives are attractive molecules for the modulation of epigenetic disorders.

  DOI：

  10.1021/jm300618u
• 作为产物：
  描述：

  4-溴苄醇 、 N-tosyl-5-bromoindole 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到1-(4-bromobenzyl)-5-bromo-1H-indole
  参考文献：
  名称：

  吲哚和苯酚与（氘代）醇盐的去甲苯基（氘代）烷基化。

  摘要：

  描述了用醇盐/醇作为烷基化试剂的吲哚和酚的N / O-（氘代）烷基化的有效策略。连续的脱甲苯基化/烷基化转化具有温和的反应条件，高的ipso-选择性和良好的官能团耐受性（> 50个例子）。还实现了未保护的吲哚与醇和TsCl的一锅选择性N-烷基化。该方法的应用通过使用易于获得的标记醇引入同位素标记（CD3和13CH3）基团以及药物合成来证明。

  DOI：

  10.1021/acs.orglett.9b02639

文献信息

• Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
  作者：Pranjal P. Bora、Manisha Bihani、Scott Plummer、Fabrice Gallou、Sachin Handa

  DOI：10.1002/cssc.201900316

  日期：2019.7.5

  Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site‐specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine‐tuning

  吲哚和芳烃的高度选择性直接单氟化是通过一种方法实现的，该方法可以使底物和氟源在胶束中发生特定位置的溶解。这种方法对具有出色的官能团耐受性的多种底物具有高度的选择性。吲哚和芳烃在胶束中的结合常数和溶解度的差异允许选择性的微调。对照实验提出了一条基本途径，并提供了对环境无害的两亲PS-750-M胶束作用的见解。动态光散射实验强烈表明了底物和氟源的特定位置溶解度。该方法已成功地适应于克规模，
• Aryl Nitriles from Alkynes Using <i>tert</i>-Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage
  作者：Uttam Dutta、David W. Lupton、Debabrata Maiti

  DOI：10.1021/acs.orglett.6b00147

  日期：2016.2.19

  Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl

  炔烃复分解之外的炔烃C≡C键断裂仍然是反应发现中一个不发达的领域。最近，据报道氮化可以使炔烃生成腈。报道了用于末端炔烃的无金属C≡C键裂解以产生腈的新方案。这种方法提供了一个机会来合成范围广泛的包含芳基，杂芳基和天然产物衍生物的腈（38个例子）。另外，证明了t BuONO用作末端芳基炔烃的强大氮化剂的潜力。
• Scalable α-Arylation of Nitriles in Aqueous Micelles using Ultrasmall Pd Nanoparticles: Surprising Formation of Carbanions in Water
  作者：Manisha Bihani、Tharique N. Ansari、Lucie Finck、Pranjal P. Bora、Jacek B. Jasinski、Bhavana Pavuluri、David K. Leahy、Sachin Handa

  DOI：10.1021/acscatal.0c01196

  日期：2020.6.19

  A scalable synthetic method is described for both the preparation of ultrasmall palladium nanoparticles and their subsequent use in catalyzing an α-arylation reaction of nitriles in aqueous micelles. This method involves the intermediacy of carbanions or keteniminates, which are presumably stabilized by the micellar environment rather than being quenched with water. These Pd nanoparticles are thoroughly

  描述了可扩展的合成方法，用于制备超小钯纳米颗粒及其在催化胶束中腈的α-芳基化反应中的后续应用。该方法涉及碳负离子或酮亚胺的中间产物，据推测是由胶束环境稳定的，而不是用水淬灭的。这些Pd纳米粒子已被彻底表征。使用31 P NMR光谱的机理研究表明，膦配体与Pd表面结合，而对照实验证实了钯的零氧化态。超过35个示例演示了转换的范围，其中一个示例的大小为50 g。
• Fe/Al pillared clay catalyzed solvent-free synthesis of bisindolylmethanes using diversely substituted indoles and carbonyl compounds
  作者：Deepak K. Sharma、Altaf Hussain、Mallikharjuna Rao Lambu、Syed Khalid Yousuf、Sudip Maiety、Baldev Singh、Debaraj Mukherjee

  DOI：10.1039/c2ra22258b

  日期：——

  A fast, solvent-free solid acid mediated synthetic strategy for the synthesis of bisindolylmethanes has been developed. The process is applicable to a wide range of substrates with different protecting group survival properties. Reusability of Fe/Al pillared clay for more than 5 cycles without significant loss of catalytic activity adds to the features of the reaction.

  我们开发了一种快速、无溶剂的固体酸介导合成双吲哚甲烷的方法。该工艺适用于多种具有不同保护基团存活特性的底物。铁/铝柱状粘土可重复使用 5 次以上而不会明显丧失催化活性，这也是该反应的一大特点。
• Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides
  作者：Ming-Hui Zhu、Cheng-Long Yu、Ya-Lan Feng、Muhammad Usman、Dayou Zhong、Xin Wang、Nasri Nesnas、Wen-Bo Liu

  DOI：10.1021/acs.orglett.9b02639

  日期：2019.9.6

  An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The

  描述了用醇盐/醇作为烷基化试剂的吲哚和酚的N / O-（氘代）烷基化的有效策略。连续的脱甲苯基化/烷基化转化具有温和的反应条件，高的ipso-选择性和良好的官能团耐受性（> 50个例子）。还实现了未保护的吲哚与醇和TsCl的一锅选择性N-烷基化。该方法的应用通过使用易于获得的标记醇引入同位素标记（CD3和13CH3）基团以及药物合成来证明。