1-(3,5-dimethoxyphenyl)butan-1-one | 39911-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-dimethoxyphenyl)butan-1-one
• 英文别名: 3',5'-Dimethoxybutyrophenone
• CAS: 39911-73-4
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: FJDZRFNDHLKABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethoxyphenyl)butan-1-one 在 ammonium acetate 、 溶剂黄146 作用下， 生成 2,3-Dicyano-3-(3,5-dimethoxy-phenyl)-hexanoic acid ethyl ester
  参考文献：
  名称：

  合成冯·哈斯基施-因哈尔施托芬（von Haschisch-Inhaltsstoffen）。6. Mitteilung †

  摘要：

  （ - ） -新的合成Δ 8 -6a，10A-反四氢大麻酚类似物含有N-甲基-3-丙基-吡咯烷-3-基侧链，则报告。

  DOI：

  10.1002/hlca.19730560149
• 作为产物：
  描述：

  1-(3,5-dimethoxyphenyl)butan-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以79%的产率得到1-(3,5-dimethoxyphenyl)butan-1-one
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v

文献信息

• Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
  作者：Mei-Ling Wang、Hui Xu、Han-Yuan Li、Biao Ma、Zhen-Yu Wang、Xing Wang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c00296

  日期：2021.3.19

  Mizoroki–Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C–C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility

  未应变的芳基酮与丙烯酸酯/苯乙烯的Mizoroki-Heck反应是通过钯催化的配体促进的C-C键裂解实现的。各种（杂）芳基酮在反应中是相容的，从而以良好至优异的产率提供了烯烃产物。在某些药物，天然产物和香料衍生的芳基酮的后期烯烃聚合中的进一步应用证明了该方案的合成效用。通过采用酮作为导向基团和离去基团二者，1,2- bifunctionalization经由顺序实现邻-C-H的烷基化/本位-Heck烯。
• Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki–Miyaura Couplings
  作者：Zhen-Yu Wang、Biao Ma、Hui Xu、Xing Wang、Xu Zhang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c03048

  日期：2021.11.5

  Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C–C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

  在此，我们报告了通过钯催化的 Suzuki-Miyaura 交叉偶联反应对芳基酮进行的芳基化、烷基化和烯基化。吡啶-恶唑啉配体的使用是断裂无应变 C-C 键的关键。源自药物和天然产物的芳基酮的后期芳基化证明了该协议的合成效用。
• Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
  作者：Hui Xu、Biao Ma、Zunyun Fu、Han-Yuan Li、Xing Wang、Zhen-Yu Wang、Ling-Jun Li、Tai-Jin Cheng、Mingyue Zheng、Hui-Xiong Dai

  DOI：10.1021/acscatal.0c05372

  日期：2021.2.5

  electrophiles via Ar–C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol

  通过Ar–C（O）裂解将众多芳基酮转化为芳基亲电体，在Sonogashira型偶联中仍然是具有挑战性但非常理想的转化。在本文中，我们报道了钯催化的配体促进的未应变芳基酮的炔基化反应。该协议允许炔基化反应以一锅法进行，具有宽泛的官能团耐受性和底物范围。该协议在药物发现和化学生物学中的潜在应用通过许多药物和天然产物的后期多样化进一步证明。更重要的是，可以通过酮的连续炔基化连接衍生自药物和天然产物的两个不同的生物学重要片段。与常规Sonogashira反应中的芳基卤化物不同，配体促进的ipso -Ar–C（O）炔基化作用使邻位C–H活化。
• Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy
  作者：Xuefeng Tan、Weijun Zeng、Jialin Wen、Xumu Zhang

  DOI：10.1021/acs.orglett.0c02565

  日期：2020.9.18

  The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C–F···Na charge–dipole interaction in

  在不对称催化中，将氟原子与氢原子区分开是具有挑战性的。我们在此报告使用动态动力学拆分策略的铱催化的α-氟代酮氢化。在制备β-氟代醇中，对映异构体和非对映异构体的选择性均令人满意。DFT计算表明，在氢化物转移的过渡态中存在CF-·Na电荷-偶极相互作用。这种非共价相互作用将负责非对映异构体的控制。
• Rh‐Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones
  作者：Kezhuo Zhang、Jiaxin Huang、Wanxiang Zhao

  DOI：10.1002/chem.202103851

  日期：2022.3.10

  A novel strategy for the preparation of ketones from aldehydes and allylic boronic esters is presented. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. This approach features mild reaction conditions, broad substrate scope, and excellent functional groups. Mechanistic studies also supported that a tandem allylation

  提出了一种由醛和烯丙基硼酸酯制备酮的新策略。该反应涉及醛与烯丙基硼酸酯的烯丙基化和高烯丙基醇的 Rh 催化链行走。该方法具有反应条件温和、底物范围广、官能团优良等特点。机理研究还支持串联烯丙基化和链式行走过程。