(R)-2-((S)-3-oxo-3-phenyl-1-(p-tolyl)propyl)cyclohexanone | 1058744-70-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-2-((S)-3-oxo-3-phenyl-1-(p-tolyl)propyl)cyclohexanone
• CAS: 1058744-70-9
• 化学式: C₂₂H₂₄O₂
• 分子量: 320.431
• InChiKey: MJRASALQHLUNPS-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((S)-3-oxo-3-phenyl-1-(p-tolyl)propyl)cyclohexanone 在 selenium(IV) oxide 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.5h， 生成 3-(4-methylphenyl)-1-phenyl-3-(4,5,6,7-tetrahydro-1,2,3-benzoselenadiazol-4-yl)-1-propanone
  参考文献：
  名称：

  A facile synthesis of carbocycle-fused mono and bis-1,2,3-selenadiazoles and their antimicrobial and antimycobacterial studies

  摘要：

  A series of mono and bis-1,2,3-selenadiazole derivatives have been synthesized by the oxidative cyclization of mono and bis semicarbazones of 2-(3-oxo-1,3-diarylpropyl)-1-cyclohexanones using selenium(IV) oxide. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 11632) and Candida albicans (ATCC 90028) and in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB). Among these compounds, 1,3-di(4-chlorophenyl)-3-(4,5,6,7-tetrahydro-1,2,3-benzoselenadiazol-4-yl)-1-propanone (2h) and 3-(4-chlorophenyl)-1-(4-methylphenyl)-3-(4,5,6,7-tetrahydro-1,2,3-benzoselenadiazol-4-yl)-1-propanone (2g) were found to be the most active compounds with MIC of 3.3 and 3.5 mu M respectively against MTB. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.007
• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 环己酮 在 对硝基苯酚 、 C₁₈H₃₄N₂ 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以92%的产率得到
  参考文献：
  名称：

  基于手性C2对称的吡咯烷基四胺催化的酮类化合物在硝基烯烃和查尔酮中的直接不对称迈克尔加成反应

  摘要：

  C 2对称的基于吡咯烷的四胺（可从商业原料获得）显示出良好的催化活性，可将酮不​​对称地迈克尔加成至硝基烯烃，特别是对查耳酮。反应进行以高收率和高度选择性的方式得到相应的产物。

  DOI：

  10.1002/cjoc.201200214

文献信息

• C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones
  作者：Shijun Ma、Lulu Wu、Ming Liu、Yongmei Wang

  DOI：10.1039/c2ob06897d

  日期：——

  A C2-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of diastereo- and enantioselectivities (up to >99 : 1 dr and 93% ee) under mild conditions. By studying the ESI-MS of the intermediates, a proposed mechanism was disclosed.

  开发了一种C 2对称四胺催化剂，用于将酮不对称地添加到查耳酮。在温和条件下，以良好的化学收率获得了相应的加合物1,5-二羰基化合物，具有很高的非对映选择性和对映选择性（高达> 99：1 dr和93％ee）。通过研究中间体的ESI-MS，公开了一种提出的机制。
• Pyrrolidine–pyridine base catalysts for the enantioselective Michael addition of ketones to chalcones
  作者：Da-Zhen Xu、Sen Shi、Yingjun Liu、Yongmei Wang

  DOI：10.1016/j.tet.2009.09.001

  日期：2009.11

  A series of pyrrolidine-pyridine base organocatalysts have been developed and 3a found to be a highly effective catalyst for the asymmetric Michael addition reactions of ketones to chalcones. The reaction generated the corresponding products 1, 5-diketones in excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 100% ee). (c) 2009 Elsevier Ltd. All rights reserved.