2-(3-phenylpropyl)cyclohexanone | 53045-12-8

• 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: 2-(3-phenylpropyl)cyclohexanone
• 英文别名: 2-(3-phenyl-propyl)-cyclohexanone；2-(3-Phenyl-propyl)-cyclohexanon；Cyclohexanone, 2-(3-phenylpropyl)-；2-(3-phenylpropyl)cyclohexan-1-one
• CAS: 53045-12-8
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: QRDUEIJUEDRPSO-UHFFFAOYSA-N

物化性质

• 沸点：
  176 °C(Press: 13 Torr)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-phenylpropyl)cyclohexanone 在 正丁基锂 、 sodium acetate 、 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 3-Dimethoxymethyl-2-(4-fluoro-phenyl)-7-(3-phenyl-propyl)-4,5,6,7-tetrahydro-2H-indazole
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024
• 作为产物：
  描述：

  1,1'-联(环己烷)-1'-烯-2-胺 在 bis-triphenylphosphine-palladium(II) chloride 、 草酸 、 caesium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.17h， 生成 2-(3-phenylpropyl)cyclohexanone
  参考文献：
  名称：

  钯催化脂肪族酮，甲酰基和硝基的分子内α-芳基化

  摘要：

  通过使用PdCl 2（Ph 3 P）2 -Cs 2 CO 3，对设计适当的带有酮，甲酰基或硝基终止基团的底物进行分子内芳构化反应体系形成各种碳环化合物。取决于环化前体的结构，酮化合物中的芳基化可提供苯环化的桥环或螺环烷酮衍生物。取决于环化前体的结构和反应溶剂，甲酰基化合物中的芳基化发生在α位置（α-芳基化）或羰基碳（羰基芳基化）。α-芳基化的仲硝基以Nef反应的方式部分转化为酮，而叔硝基被部分消除，得到苯乙烯型烯烃。

  DOI：

  10.1016/j.tet.2004.09.112

文献信息

• Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines
  作者：Pandula T. Kirinde Arachchige、Suhashini Handunneththige、Marat R. Talipov、Nishantha Kalutharage、Chae S. Yi

  DOI：10.1021/acscatal.1c04732

  日期：2021.11.19

  mediate a regioselective deaminative coupling reaction of ketones with amines to form the α-alkylated ketone products. Both benzylic and aliphatic primary amines were found to be suitable substrates for the coupling reaction with ketones in forming the α-alkylated ketone products. The coupling reaction of PhCOCD3 with 4-methoxybenzylamine showed an extensive H/D exchange on both α-CH2 (41% D) and β-CH2

  发现由阳离子 Ru-H 配合物与 3,4,5,6-四氯-1,2-苯醌反应原位形成的催化体系介导酮与胺的区域选择性脱氨基偶联反应，形成α-烷基化酮产品。发现苄基和脂肪族伯胺都是与酮偶联反应形成α-烷基化酮产物的合适底物。PhCOCD 3与4-甲氧基苄胺的偶联反应在烷基化产物的α-CH 2 (41% D)和β-CH 2 (21%)位置上显示出广泛的H/D交换。从苯乙酮与对位取代苄胺p- XC反应获得的哈米特图6 H 4 CH 2 NH 2 (X = OMe, Me, H, F, Cl, CF 3 ) 显示出具有电子释放基团的胺底物的强烈促进作用 (ρ = -0.49 ± 0.1)。在苯乙酮与 4-甲氧基苄胺偶联反应的烷基化产物 ( C α = 1.020)的 α-碳上观察到最显着的碳同位素效应。来自分离的亚胺底物的烷基化反应动力学导致经验速率定律：速率 = k [Ru][亚胺]。通过阳离子 Ru-H
• Intramolecular Reactions of Benzylic Azides with Ketones:  Competition between Schmidt and Mannich Pathways
  作者：Aaron Wrobleski、Jeffrey Aubé

  DOI：10.1021/jo001367p

  日期：2001.2.1

  The Lewis acid-promoted reactions of benzylic azides with ketones can proceed by two major pathways. The azido-Schmidt reaction involves simple addition of azide to the ketone followed by rearrangement and ring expansion. In addition, benzylic azides can undergo prior rearrangement to afford iminium ions that can subsequently participate in a Mannich reaction. A series of ketones containing an alpha CH2(CH2)nCH(N3)Ph

  路易斯酸促进的苄基叠氮化物与酮的反应可以通过两个主要途径进行。叠氮基-施密特反应涉及将叠氮化物简单地添加到酮中，然后重排和扩环。另外，苄基叠氮化物可先进行重排以提供亚胺离子，其随后可参与曼尼希反应。制备了一系列含有αCH2（CH2）nCH（N3）Ph取代基（n = 1-3）的酮，以研究产物对酮环尺寸和系链长度的依赖性。对于所有检查的酮类，当使用四碳连接剂时（上述配方中的n = 1），由于分子内Schmidt反应而获得的双环内酰胺的收率很高，但曼尼希产品主要用于较长的拴系剂（n = 2，3）。 ）。
• Kinetic resolution of α-substituted ketones by Wittig reaction using a chiral tricyclic phosphonate
  作者：Koichi Narasaka、Eri Hidai、Yujiro Hayashi、Jean-Louis Gras

  DOI：10.1039/c39930000102

  日期：——

  Wittig reactions of α-substituted ketones using a chiral phosphonate derived from mannitol afford chiral olefins by kinetic resolution.

  使用甘露醇衍生的手性膦酸盐进行δ-取代酮的 Wittig 反应，通过动力学解析生成手性烯烃。
• Palladium-Catalyzed Intramolecular α-Arylation of Aliphatic Ketones
  作者：Hideaki Muratake、Mitsutaka Natsume

  DOI：10.1016/s0040-4039(97)01787-5

  日期：1997.10

  Cyclization reaction of 5 – 10 using 10 mol% of PdCl2(Ph3P)2 in the presence of 3 eq. of Cs2CO3 in hot THF or toluene afforded bridged or spiro compounds 11 – 16 in good to modest yields. © 1997 Elsevier Science Ltd.

  的环化反应5 - 10使用10摩尔％的PdCl的2（PH 3 P）2在3当量的存在。的铯2 CO 3在热THF或甲苯，得到桥接或螺环化合物11 - 16以优良至适中的产率。©1997爱思唯尔科学有限公司。
• Iron-Catalyzed Cyanide-Free Synthesis of Alkyl Nitriles: Oxidative Deconstruction of Cycloalkanones with Ammonium Salts and Aerobic Oxidation
  作者：Hong Xin、Mingyu Yang、Cheng Guan、Jialong Li、Pin Gao、Xu Yang、Xin-Hua Duan、Li-Na Guo

  DOI：10.1021/acs.orglett.4c00458

  日期：2024.3.22

  A sustainable, cyanide-free synthesis of alkyl nitriles via the aerobic oxidative deconstruction of unstrained cycloalkanones with ammonium salts has been developed. Using inexpensive and stable ammonium salts as the nitrogen source, a variety of alkyl nitriles containing a distal carbonyl group were obtained in good yields under visible-light-promoted iron catalysis. This protocol is characterized

  通过用铵盐对无张力环烷酮进行有氧氧化解构，开发了一种可持续、无氰化物的烷基腈合成方法。使用廉价且稳定的铵盐作为氮源，在可见光促进的铁催化下以良好的收率获得了多种含有远端羰基的烷基腈。该方案的特点是条件温和、材料丰富且环境友好、原子和步骤经济性高、废物产生最少。主要机理研究表明1 O 2很可能参与该反应。