1-(4-methoxy-phenyl)-nonan-1-one | 52754-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxy-phenyl)-nonan-1-one
• 英文别名: 1-(4-methoxyphenyl)nonan-1-one；p-anisyl octyl ketone；1-(4-Methoxy-phenyl)-nonan-1-on；4'-methoxynonanophenone；p-Methoxynonanophenon
• CAS: 52754-68-4
• 化学式: C₁₆H₂₄O₂
• mdl: MFCD01097365
• 分子量: 248.365
• InChiKey: HKMYZRGEJASUJM-UHFFFAOYSA-N

物化性质

• 熔点：
  119-119.5 °C
• 沸点：
  365.3±15.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• 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：

  1-(4-methoxy-phenyl)-nonan-1-one 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5-(4-Methoxy-phenyl)-trideca-2,4-dienoic acid (1-methyl-4-pyridin-3-yl-butyl)-amide
  参考文献：
  名称：

  Pentadienyl carboxamide derivatives as antagonists of platelet activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,-E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxy-phenyl)-N- [1-methyl-4-(3-pyridinyl)butyl]- 2,4-pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4- (3-pyridinyl)butyl]-2,4-decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H- 1-(4-morpholinyl)-1-propanone (45).

  DOI：

  10.1021/jm00128a026
• 作为产物：
  描述：

  在 tetrabutylammonium borohydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以0.359 g的产率得到1-(4-methoxy-phenyl)-nonan-1-one
  参考文献：
  名称：

  通过可控的β-羟基磺酰基中间体的顺/反片段化立体合成烯烃。

  摘要：

  酰化的三氟乙基链烷磺酸盐中羰基的还原遵循Felkin-Ahn选择性，并且根据反应条件，如此形成的非对映异构体β-羟基磺酰基中间体会发生合成和反片段化。实际上，以立体发散的方式形成异构的E-和Z-烯烃，其模仿了Peterson烯烃化反应的机理。

  DOI：

  10.1039/c9ob01563a

文献信息

• Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents
  作者：Souya Dohi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2012.05.059

  日期：2012.8

  groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well

  通过衍生自芳基或烷基溴化物的格利雅试剂的反应，然后与芳族或脂族醛的反应以及随后用1,3-二碘的处理，可以有效地以高收率高效地制备各种二芳基酮，烷基芳基酮和二烷基酮。一锅法中的-5,5-二甲基乙内酰脲和K 2 CO 3。相同的处理的芳族溴化物轴承吸电子基团，如酯，腈，酮和硝基与我-PrMgCl·LiCl或PhMgCl代替Mg，也以良好的收率提供了相应的二芳基和烷基芳基酮。以上方法是用于制备各种带有富电子芳族基团和缺电子芳族基团的二芳基酮和烷基芳基酮以及二烷基酮的简单且实用的无过渡金属的方法。
• Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system
  作者：Nicolas R. Vautravers、Damien D. Regent、Bernhard Breit

  DOI：10.1039/c1cc10683j

  日期：——

  Based on a conceptually innovative bifunctional P,N ligand, an efficient protocol for the rhodium-catalyzed inter- and intramolecular hydroacylation of alkenes has been developed.

  基于概念上创新的双功能P，N配体，已开发出铑催化烯烃分子间和分子内加氢酰化的有效方案。
• Synthesis of Alkyl Aryl Ketones by Pd/Light Induced Carbonylative Cross-Coupling of Alkyl Iodides and Arylboronic Acids
  作者：Shuhei Sumino、Takahito Ui、Ilhyong Ryu

  DOI：10.1021/ol401363t

  日期：2013.6.21

  Alkyl aryl ketones were synthesized by the carbonylative cross-coupling reaction of alkyl iodides and arylboronic acids under combined Pd/light conditions. In this reaction, it is likely that an acylpalladium species would be formed via carbonylation of the alkyl radical, which would then undergo transmetalation of an arylboronic acid to give the corresponding acyl(aryl)palladium species, ready to

  烷基芳基酮是通过在碘化钯/轻质条件下烷基碘化物和芳基硼​​酸的羰基交叉偶联反应合成的。在该反应中，很可能通过烷基的羰基化形成酰基铝物种，然后对芳基硼酸进行金属转移，得到相应的酰基（芳基）钯物种，准备进行还原消除以生成烷基。芳基酮。
• Cu/Mn bimetallic catalysis enables carbonylative Suzuki–Miyaura coupling with unactivated alkyl electrophiles
  作者：Dominic R. Pye、Li-Jie Cheng、Neal P. Mankad

  DOI：10.1039/c7sc01170a

  日期：——

  carbonylative C–C coupling of arylboronic esters with alkyl halides, allowing for the convergent synthesis of ketones. The system operates under mild conditions and exhibits complementary reactivity to Pd catalysis. The method is compatible with a wide range of arylboronic ester nucleophiles and proceeds smoothly for both primary and secondary alkyl iodide electrophiles. Preliminary mechanistic experiments

  由铜-卡宾和锰-羰基助催化剂组成的双金属体系被用于芳基硼酸酯与烷基卤的羰基化碳-碳偶联，从而可以收敛地合成酮。该系统在温和条件下运行，并表现出与Pd催化互补的反应性。该方法与广泛的芳基硼酸酯亲核试剂兼容，并且对于伯和仲烷基碘亲电试剂均能顺利进行。初步的力学实验证实了由相互依赖的循环组成的假设催化机制，其中Cu-卡宾助催化剂进行金属转移以生成有机铜亲核试剂，Mn-羰基助催化剂通过单电子转移活化卤代烷亲电子体，然后进行可逆羰基化反应生成酰基锰亲电子体。然后，两个循环与异双金属，释放产物的C–C偶联步骤相交。
• Palladium-Catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of Pyrazolones Enabled by α-(Trifluoromethyl)alkenyl Acetates
  作者：Dong Li、Wande Zhang、Shuaibo Zhang、Wuding Sun、Jinfeng Zhao、Baomin Wang、Jingping Qu、Yuhan Zhou

  DOI：10.1021/acs.orglett.1c01957

  日期：2021.8.6

  pyrazolones using α-(trifluoromethyl)alkenyl acetates as a novel trifluoromethylated allylation reagent is described, affording various functionalized chiral pyrazolones containing a trifluoromethylated allyl substituent in high yields with excellent regio-/enantio-/diastereoselectivities. Mechanistically, the double-bond migration of α-(trifluoromethyl)alkenyl acetates in the presence of 1,8-diazabicyclo[5

  描述了使用 α-(三氟甲基) 烯基乙酸酯作为新型三氟甲基化烯丙基化试剂的吡唑啉酮的第一个不对称三氟甲基化烯丙基烷基化，以高产率提供各种含有三氟甲基化烯丙基取代基的官能化手性吡唑啉酮，并具有优异的区域-/对映-/非对映选择性。从机理上讲，在 1,8-二氮杂双环 [5.4.0] undec-7-ene 存在下，α-（三氟甲基）烯基乙酸酯的双键迁移是初始且有趣的步骤。更重要的是，该研究对于提供一种新型且广泛适用的含三氟甲基的烯丙基化试剂具有重要意义。