4-氰基-4-(4-溴苯基)环己酮 | 65619-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氰基-4-(4-溴苯基)环己酮
• 英文名称: 1-(4-bromophenyl)-4-oxocyclohexane-1-carbonitrile
• 英文别名: 1-(4-Bromophenyl)-4-oxocyclohexanecarbonitrile
• CAS: 65619-28-5
• 化学式: C₁₃H₁₂BrNO
• 分子量: 278.148
• InChiKey: KTUMOHADVSXZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4-氰基-4-(4-溴苯基)环己酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇 、 苯 为溶剂， 反应 42.0h， 生成 4-(p-bromophenyl)-4-dimethylaminocyclohexan-1-one. ethylene ketal
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  4-(p-Bromphenyl)-4-cyanopimelinsaeuredimethylester 在 硫酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 生成 4-氰基-4-(4-溴苯基)环己酮
  参考文献：
  名称：

  DE2723937

  摘要：

  公开号：

文献信息

• CHEMOSELECTIVE METHYLENE HYDROXYLATION IN AROMATIC MOLECULES
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20200087331A1

  公开（公告）日：2020-03-19

  A chemoselective and reactive Mn(CF 3 -PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

  一种化学选择性和反应性的Mn(CF3-PDP)催化体系首次实现了后期脂肪族C—H羟基化在芳香化合物中的战略优势。这一发现将有助于小分子药物的快速多样化和芳香类药物以及天然产物的代谢产物的鉴定。
• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR TRAITER DES ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE ACTIVITÉ DE STING
  申请人：IFM DUE INC

  公开号：WO2022015977A1

  公开（公告）日：2022-01-20

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

  本公开涉及化学实体（例如，化合物或药物可接受的盐，水合物，共晶体或化合物的药物组合），其抑制（例如，对抗）干扰素基因刺激剂（STING）。这些化学实体是有用的，例如，用于治疗在该主题（例如，人类）中增加（例如，过度）STING激活（例如，STING信号传导）对病理学和/或症状和/或病情进展有贡献的状况，疾病或障碍（例如，癌症）。本公开还涉及包含相同的组合物以及使用和制造相同的方法。
• Chemoselective methylene oxidation in aromatic molecules
  作者：Jinpeng Zhao、Takeshi Nanjo、Emilio C. de Lucca、M. Christina White

  DOI：10.1038/s41557-018-0175-8

  日期：2019.3

  labile aromatic functionalities remains a major unsolved problem. Such chemoselective reactivity is highly desirable for enabling late-stage oxidative derivatizations of pharmaceuticals and medicinally important natural products that often contain such functionality. Here, we report a simple manganese small-molecule catalyst Mn(CF3–PDP) system that achieves such chemoselectivity via an unexpected synergy

  尽管在过去十年中，位点选择性脂肪族C–H氧化的发展取得了重大进展，但是在存在更多易氧化的芳族官能团的情况下，能够氧化亚甲基C–H强键的能力仍然是一个主要未解决的问题。这种化学选择性反应性对于使通常包含这种功能性的药物和重要的天然药物能够进行后期的氧化衍生化是非常需要的。在这里，我们报告了一种简单的锰小分子催化剂Mn（CF 3-PDP）系统通过催化剂设计和酸添加剂的意外协同作用实现了这种化学选择性。在50种芳香族化合物中可进行制备型亚甲基远距离氧化，这些芳香族化合物具有可药用的卤素，氧，杂环和联芳基部分。在四种药物支架上均显示了晚期亚甲基氧化，包括乙炔雌二醇支架，在该支架上，其他可耐受芳香族基团的非定向CH氧化剂仅在活化的叔苄基位上进行氧化。证明了从高级中间体快速生成已知代谢物（吡拉格列汀）的方法。
• SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS
  申请人：Plettenburg Oliver

  公开号：US20110190341A1

  公开（公告）日：2011-08-04

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  本发明涉及公式（I）的取代异喹啉和异喹啉酮，用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶的磷酸化相关的疾病，以及含有这些化合物的组合物。
• Chemoselective methylene hydroxylation in aromatic molecules
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10961266B2

  公开（公告）日：2021-03-30

  A chemoselective and reactive Mn(CF3-PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

  一种化学选择性和反应性 Mn（CF3-PDP）催化剂系统，首次在芳香化合物中发挥了后期脂肪族 C-H 羟基化的战略优势。这一发现将使芳香族药物和天然产物迅速多样化并鉴定其代谢物，从而有利于小分子疗法。