octyl 3-nitro-5-(trifluoromethyl)benzoate | 203513-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: octyl 3-nitro-5-(trifluoromethyl)benzoate
• CAS: 203513-25-1
• 化学式: C₁₆H₂₀F₃NO₄
• 分子量: 347.334
• InChiKey: AWLJNUCIHXMRNS-UHFFFAOYSA-N

物化性质

• 沸点：
  389.5±42.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 3-nitro-5-(trifluoromethyl)benzoate 在 palladium on activated charcoal Amberlyst A-21 ion-exchange resin 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 18.3h， 生成 3-[(2-Chloro-4-trifluoromethyl-pyrimidine-5-carbonyl)-amino]-5-trifluoromethyl-benzoic acid octyl ester
  参考文献：
  名称：

  2-Chloro-4-(trifluoromethyl)pyrimidine-5-N-(3‘,5‘-bis(trifluoromethyl)phenyl)- carboxamide:  A Potent Inhibitor of NF-κB- and AP-1-Mediated Gene Expression Identified Using Solution-Phase Combinatorial Chemistry

  摘要：

  Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-kB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution-phase parallel synthesis, inhibitors of both NF-kB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-kB as potential therapeutic targets. The synthesis and preliminary structure-activity relationships of these compounds is addressed.

  DOI：

  10.1021/jm970671g
• 作为产物：
  描述：

  3-三氟甲基苯甲酸 在 nitronium tetrafluoborate 、 氢气 作用下， 以 环丁砜 为溶剂， 生成 octyl 3-nitro-5-(trifluoromethyl)benzoate
  参考文献：
  名称：

  Altering the Stereochemistry of Allylation Reactions of Cyclic .alpha.-Sulfinyl Radicals with Diarylureas

  摘要：

  Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis[3-(trifluoromethyl)-5-(carbooctyloxy)phenyl] urea have been investigated. This urea was shown to be about as selective at promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.

  DOI：

  10.1021/jo00091a007

文献信息

• Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer
  作者：Amanda K. Turek、David J. Hardee、Andrew M. Ullman、Daniel G. Nocera、Eric N. Jacobsen

  DOI：10.1002/anie.201508060

  日期：2016.1.11

  towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron‐deficient quinones are used. We have successfully employed HBD‐coupled electron transfer as a strategy to activate electron‐deficient quinones

  在各种合成和生物学环境中，醌是重要的有机氧化剂，它们很容易通过氢键活化为电子转移。尽管已经观察到路易斯碱性弱氧化醌的氢键供体（HBD）的这种作用，但是当使用反应性更强和合成上有用的缺电子醌时，很难实现可比的活化。我们已经成功地将HBD耦合电子转移作为激活缺电子醌的策略。对HBD的系统研究导致发现某些特定的HBD对电子转移的速率和热力学具有极大的影响。我们进一步证明，这些HBD可用作醌介导的模型合成转化中的催化剂。
• Altering the Stereochemistry of Allylation Reactions of Cyclic .alpha.-Sulfinyl Radicals with Diarylureas
  作者：Dennis P. Curran、Lung Huang Kuo

  DOI：10.1021/jo00091a007

  日期：1994.6

  Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis[3-(trifluoromethyl)-5-(carbooctyloxy)phenyl] urea have been investigated. This urea was shown to be about as selective at promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.
• 2-Chloro-4-(trifluoromethyl)pyrimidine-5-<i>N</i>-(3‘,5‘-bis(trifluoromethyl)phenyl)- carboxamide:  A Potent Inhibitor of NF-κB- and AP-1-Mediated Gene Expression Identified Using Solution-Phase Combinatorial Chemistry
  作者：Robert W. Sullivan、Colin G. Bigam、Paul E. Erdman、Moorthy S. S. Palanki、David W. Anderson、Mark E. Goldman、Lynn J. Ransone、Mark J. Suto

  DOI：10.1021/jm970671g

  日期：1998.2.1

  Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-kB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution-phase parallel synthesis, inhibitors of both NF-kB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-kB as potential therapeutic targets. The synthesis and preliminary structure-activity relationships of these compounds is addressed.