1-Bromcyclopentyl-p-methylphenylketon | 6758-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Bromcyclopentyl-p-methylphenylketon
• 英文别名: (1-Bromocyclopentyl)-(4-methylphenyl)methanone；(1-bromocyclopentyl)-(4-methylphenyl)methanone
• CAS: 6758-17-4
• 化学式: C₁₃H₁₅BrO
• 分子量: 267.166
• InChiKey: VZYPAOWHVKLEEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Bromcyclopentyl-p-methylphenylketon 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以550 mg的产率得到(1-azidocyclopentyl)(p-tolyl)methanone
  参考文献：
  名称：

  铁催化的叔α-叠氮基酮的酰基迁移：酰胺和异喹诺酮类化合物的合成方法。

  摘要：

  本文报道，在较高的温度下，通过在DMF中用FeBr 2处理，可以将叔α-叠氮基苯基酮转化为酰胺。该反应通过从α-碳到氮原子的1，2-苯甲酰基迁移而伴随着氮分子的排出而进行。该方案适用于合成N-（环戊-1-烯-1-基）苯甲酰胺，N-（环己-1-烯-1-基）苯甲酰胺和N-苯甲酰基-α-甲基烯胺。异喹诺酮类的简便治疗方法。

  DOI：

  10.1021/acs.orglett.8b00409
• 作为产物：
  描述：

  环戊基(4-甲基苯基)甲酮 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 1-Bromcyclopentyl-p-methylphenylketon
  参考文献：
  名称：

  N，N'-二氧化物-金属络合物催化α-酮醇，α-羟基醛和α-氨基缩醛的不对称酰基环重排。

  摘要：

  环状α-酮醇的高度对映选择性酰基肌醇重排反应已经开发出来，其中手性Al（III）–N，N'-二氧化物配合物为催化剂。该策略以中等到良好的产率和高对映选择性提供了一系列光学活性的2-酰基-2-羟基环己酮。在改性条件下也可以实现无环α-羟基醛和α-亚氨基的不对称异构化，得到中等程度的相应手性α-羟基酮和α-氨基酮。此外，将产物进一步转化为对映体富集的二醇。

  DOI：

  10.1021/acs.orglett.0c01626

文献信息

• Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by <i>N</i>,<i>N</i>′-Dioxide–Metal Complexes
  作者：Li Dai、Xiangqiang Li、Zi Zeng、Shunxi Dong、Yuqiao Zhou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acs.orglett.0c01626

  日期：2020.7.2

  N′-dioxide complex as catalyst. This strategy provided an array of optically active 2-acyl-2-hydroxy cyclohexanones in moderate to good yields with high enantioselectivities. The asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions, affording the corresponding chiral α-hydroxy ketones and α-amino ketones in moderate results. Moreover, further

  环状α-酮醇的高度对映选择性酰基肌醇重排反应已经开发出来，其中手性Al（III）–N，N'-二氧化物配合物为催化剂。该策略以中等到良好的产率和高对映选择性提供了一系列光学活性的2-酰基-2-羟基环己酮。在改性条件下也可以实现无环α-羟基醛和α-亚氨基的不对称异构化，得到中等程度的相应手性α-羟基酮和α-氨基酮。此外，将产物进一步转化为对映体富集的二醇。
• Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
  作者：Tonghao Yang、Xing Fan、Xiaopeng Zhao、Wei Yu

  DOI：10.1021/acs.orglett.8b00409

  日期：2018.4.6

  transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones

  本文报道，在较高的温度下，通过在DMF中用FeBr 2处理，可以将叔α-叠氮基苯基酮转化为酰胺。该反应通过从α-碳到氮原子的1，2-苯甲酰基迁移而伴随着氮分子的排出而进行。该方案适用于合成N-（环戊-1-烯-1-基）苯甲酰胺，N-（环己-1-烯-1-基）苯甲酰胺和N-苯甲酰基-α-甲基烯胺。异喹诺酮类的简便治疗方法。
• Discovery of novel ketamine‐inspired derivatives as a protective agent against renal ischemic/reperfusion injury in Wistar rats
  作者：Li Zhu、Yin Zhang

  DOI：10.1111/cbdd.14011

  日期：2022.7

  AbstractRenal ischemia‐reperfusion (I/R) injury is a limiting factor for the success of renal grafts and is deemed greatly responsible for the mortality. A novel series of ketamine‐inspired compounds was synthesized and subjected to NF‐ĸB transcriptional inhibitory activity in LPS‐stimulated RAW264.7 cells, where entire set of compounds showed mild‐to‐moderate significant NF‐ĸB transcriptional inhibitory activity (IC50 6.53–67.52 µM). Compound 6d showed highest inhibitory activity among the tested series (IC50 2.62 µM) and found more potent as compared to ketamine as standard. The effect of compound 6d was further quantified in I/R injury in Wistar rats, where it dose‐dependently improves kidney function of rats with significant amelioration of kidney injury as suggested by histopathologic examination of renal tissues. It further showed reduction in the generation of pro‐inflammatory cytokines and improves the antioxidant status of experimental rats. Compound 6d inhibited apoptosis and increases the expression of Bcl2 and decreases Bax, and cleaved caspase‐3 level. It further reduces TLR‐4 and NF‐κB expression in renal cells of rats, with increases in IκB‐α level in Western blot analysis as compared to I/R group. In summary, our current study showed the development of a novel class of ketamine‐inspired derivatives against renal ischemia/reperfusion injury.