(R)-5-methyl-2-(phenylsulfinyl)cyclohex-2-en-1-one | 790699-53-5

• 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: (R)-5-methyl-2-(phenylsulfinyl)cyclohex-2-en-1-one
• 英文别名: (5R)-2-(benzenesulfinyl)-5-methylcyclohex-2-en-1-one
• CAS: 790699-53-5
• 化学式: C₁₃H₁₄O₂S
• 分子量: 234.319
• InChiKey: WNAKKXCXESNPIF-HQNRFAHOSA-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-methyl-2-(phenylsulfinyl)cyclohex-2-en-1-one 在 copper(l) iodide 、 calcium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 25.75h， 生成 (R)-(-)-3,5-dimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  来自 (R)-Pulegone 的 (R)- 和 (S)-3,5-Dimethylcyclohex-2-en-1-ones 的对映发散合成

  摘要：

  摘要 R-(+)-pulegone (1) 转化为 (R)-5-methyl-2-(phenylsulfinyl)cyclohexanone (5)（65%，3 个步骤）。亚砜 5 转化为 R-(-)-3,5-二甲基环己-2-en-1-one (4)（53%，4 步）和 S-(+)-4（26%，3 步）。

  DOI：

  10.1080/00397919408010206
• 作为产物：
  描述：

  (R)-(+)-3-甲基环己酮 在 potassium tert-butylate 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-5-methyl-2-(phenylsulfinyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  New DNA binding ligands as a model of chromomycin A3

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A(3) (CRA(3)) which contains a hydroxylated tetrahydroanthracene chromophore substituted with di and trisaccharides. The trisaccharide part of CRA(3) that is supposed to contribute to form the Mg2+-coordinated dimer was expected to be mimicked by a simple alkyl group attached to the chromophore part as new model compounds. The present study has successfully demonstrated that the new ligands form Mg2+-coordinated dimer complexes to exhibit DNA-binding affinity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.043

文献信息

• Protection of all cleavable sites of DNA with the multiple CGCG or continuous CGG sites from the restriction enzyme, indicative of simultaneous binding of small ligands
  作者：Hirotaka Murase、Gentaro Wakisaka、Tomoharu Noguchi、Shigeki Sasaki

  DOI：10.1016/j.bmc.2020.115730

  日期：2020.10

  synthesized and evaluated by a restriction enzyme inhibition assay. DNA substrates composed of multiple CGCG or CGG sites are fully hydrolyzed by a restriction enzyme that is selective for each sequence. Under such conditions, the full-length DNA substrate remains only when the ligand binds to all binding sites and protects it from hydrolysis by the restriction enzymes. In the assay using AccII and the

  合成了具有酮酚和异羟肟酸单元的蒽酮配体（1 – 12），并通过限制酶抑制试验进行了评估。由多个CGCG或CGG位点组成的DNA底物被对每个序列具有选择性的限制酶完全水解。在这种条件下，全长DNA底物仅在配体结合所有结合位点并保护其不受限制酶水解时保留。在使用Acc II和以不同的非结合AT碱基对间隔包含不同数量CGCG位点的50-mer DNA底物的测定中，CGCG位点越多，全长DNA越增加。即同时结合配体（5）到CGCG的位置按（CGCG）5 >（CGCG）2 >（CGCG）1的顺序增加。此外，异羟肟酸与蒽酮骨架的间隔长度在CGCG位点之间的d（A / T）碱基对数目的偏爱中起着重要作用。长的间隔配体（5）相对于具有五个AT对的CGCG位点优先，而短的间隔配体（10）相对于具有两个AT对的CGCG位点优先。在使用限制性内切酶Fnu的测定中，间隔最短的配体（12）在同时结合由16个连续CGG位点组成的54-mer
• Stereoselective synthesis of (+)-2-deoxyolivin based on cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivative
  作者：Yoshinari Haruta、Kazumitsu Onizuka、Kyouichi Watanabe、Kyoko Kono、Akihiro Nohara、Kenichi Kubota、Shuhei Imoto、Shigeki Sasaki

  DOI：10.1016/j.tet.2008.05.080

  日期：2008.7

  tricyclic aglycon core, olivin. In this study, we established the efficient synthesis of the anthracenone core skeleton based on a cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivatives, which is promoted by the combined use of molecular sieves, proton sponge, and a Lewis acid. The cyclohexenone with four chiral centers was synthesized by asymmetric and diastereoselective

  olivomycins是该化合物的aureolic家族中的代表性抗肿瘤抗生素，其包含三环糖苷配基核心olivin。在这项研究中，我们建立了基于间苯二甲酸酐与手性环己烯酮衍生物之间的环加成反应的蒽环核心骨架的有效合成方法，该反应可通过分子筛，质子海绵和路易斯酸的组合使用而得到促进。通过不对称和非对映选择性反应合成具有四个手性中心的环己烯酮，并使其与高邻苯二甲酸酐进行环加成反应，然后进行一系列反应以完成（+）-2-脱氧低聚香醇的立体选择性合成。
• Enantiodivergent Syntheses of (R)- and (S)-3,5-Dimethylcyclohex-2-en-1-ones from (R)-Pulegone
  作者：A. Nangia、G. Prasuna

  DOI：10.1080/00397919408010206

  日期：1994.7

  Abstract R-(+)-pulegone (1) is transformed to (R)-5-methyl-2-(phenylsulfinyl)cyclohexanone (5) (65%, 3 steps). Sulfoxide 5 is converted to R-(-)-3,5-dimethylcyclohex-2-en-1-one (4) (53%, 4 steps) and S-(+)-4 (26%, 3 steps).

  摘要 R-(+)-pulegone (1) 转化为 (R)-5-methyl-2-(phenylsulfinyl)cyclohexanone (5)（65%，3 个步骤）。亚砜 5 转化为 R-(-)-3,5-二甲基环己-2-en-1-one (4)（53%，4 步）和 S-(+)-4（26%，3 步）。
• New DNA binding ligands as a model of chromomycin A3
  作者：Shuhei Imoto、Yoshinari Haruta、Kyouichi Watanabe、Shigeki Sasaki

  DOI：10.1016/j.bmcl.2004.07.043

  日期：2004.10

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A(3) (CRA(3)) which contains a hydroxylated tetrahydroanthracene chromophore substituted with di and trisaccharides. The trisaccharide part of CRA(3) that is supposed to contribute to form the Mg2+-coordinated dimer was expected to be mimicked by a simple alkyl group attached to the chromophore part as new model compounds. The present study has successfully demonstrated that the new ligands form Mg2+-coordinated dimer complexes to exhibit DNA-binding affinity. (C) 2004 Elsevier Ltd. All rights reserved.