cyclooctyl(4-methoxyphenyl)methanone | 108395-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclooctyl(4-methoxyphenyl)methanone
• 英文别名: Cyclooctyl-(4-methoxyphenyl)methanone
• CAS: 108395-08-0
• 化学式: C₁₆H₂₂O₂
• mdl: MFCD20947200
• 分子量: 246.349
• InChiKey: KJPHEOWUSROGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴嘧啶 、 cyclooctyl(4-methoxyphenyl)methanone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以18%的产率得到Cyclooctyl-(4-methoxy-phenyl)-pyrimidin-5-yl-methanol
  参考文献：
  名称：

  Aromatase inhibition by 5-substituted pyrimidines and dihydropyrimidines

  摘要：

  The inhibition of estrogen biosynthesis has been suggested to be an effective treatment of hormone-dependent diseases, particularly breast cancer. Several series of 5-substituted pyrimidine derivatives have been synthesized and tested for their ability to inhibit the enzyme aromatase (estrogen synthetase). Compounds were evaluated in an in vitro assay that measured the inhibition of rat ovarian microsomal aromatase activity. Greatest inhibitory activity was achieved in the cases of diarylpyrimidinemethanols and diarylpyrimidinyl methanes which were substituted in the 4- and 4'-positions with electron-withdrawing substituents, particularly Cl.

  DOI：

  10.1021/jm00391a016
• 作为产物：
  描述：

  环辛醇 在 咪唑 、 potassium tert-butylate 、 碘 、 C₂₉H₄₀N₃O₂⁽¹⁺⁾*F₆P^(1-) 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 cyclooctyl(4-methoxyphenyl)methanone
  参考文献：
  名称：

  中离子卡宾催化醛的甲酰基烷基化

  摘要：

  以中离子卡宾 (MIC) 为催化剂，成功开发了一种用于醛和烷基卤化物偶联反应的无金属方案。这种多功能的策略通过后期功能化提供了多种多样的简单酮和生物活性分子。

  DOI：

  10.1002/anie.202303478

文献信息

• Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp³)–H Bond
  作者：Xinying Zhang、Zhangxin Wang、Xuesen Fan、Jianji Wang

  DOI：10.1021/acs.joc.5b01824

  日期：2015.11.6

  In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp(3))-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.
• TAYLOR, H. M.;JONES, C. D.;DAVENPORT, J. D.;HIRSCH, K. S.;KRESS, T. J.;WE+, J. MED. CHEM., 30,(1987) N 8, 1359-1365
  作者：TAYLOR, H. M.、JONES, C. D.、DAVENPORT, J. D.、HIRSCH, K. S.、KRESS, T. J.、WE+

  DOI：——

  日期：——
• Aromatase inhibition by 5-substituted pyrimidines and dihydropyrimidines
  作者：Harold M. Taylor、C. David Jones、James D. Davenport、Kenneth S. Hirsch、T. J. Kress、Dix Weaver

  DOI：10.1021/jm00391a016

  日期：1987.8

  The inhibition of estrogen biosynthesis has been suggested to be an effective treatment of hormone-dependent diseases, particularly breast cancer. Several series of 5-substituted pyrimidine derivatives have been synthesized and tested for their ability to inhibit the enzyme aromatase (estrogen synthetase). Compounds were evaluated in an in vitro assay that measured the inhibition of rat ovarian microsomal aromatase activity. Greatest inhibitory activity was achieved in the cases of diarylpyrimidinemethanols and diarylpyrimidinyl methanes which were substituted in the 4- and 4'-positions with electron-withdrawing substituents, particularly Cl.
• Mesoionic Carbene‐Catalyzed Formyl Alkylation of Aldehydes
  作者：Chang Liu、Zengyu Zhang、Liang‐Liang Zhao、Guy Bertrand、Xiaoyu Yan

  DOI：10.1002/anie.202303478

  日期：2023.6.12

  A metal-free protocol for the coupling reaction of aldehydes and alkyl halides was successfully developed with mesoionic carbenes (MICs) as catalysts. This versatile strategy delivers a large diversity of simple ketones as well as bio-active molecules by late-stage functionalization.

  以中离子卡宾 (MIC) 为催化剂，成功开发了一种用于醛和烷基卤化物偶联反应的无金属方案。这种多功能的策略通过后期功能化提供了多种多样的简单酮和生物活性分子。