1-(2,4-dimethoxyphenyl)pentan-1-one | 854659-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4-dimethoxyphenyl)pentan-1-one
• 英文别名: 1-(2,4-Dimethoxyphenyl)pentan-1-one
• CAS: 854659-33-9
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: NAKWTGBULLMEFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-(2,4-dimethoxyphenyl)pentan-1-one 在 palladium on activated charcoal sodium tetrahydroborate 、 三氯化铝 、 氢气 、 三溴化硼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -18.0~25.0 ℃ 、206.84 kPa 条件下， 反应 20.67h， 生成 1-(2,4-dihydroxy-5-pentyl-phenyl)-ethanone
  参考文献：
  名称：

  白三烯B4受体拮抗剂：LY255283系列羟基苯乙酮。

  摘要：

  制备了一系列羟基苯乙酮作为白三烯B4（LTB4）受体拮抗剂进行评估，最终以1- [5-乙基-2-羟基-4-[[6-甲基-6-（1H-四唑-5-基）庚基] [氧基]苯基]乙酮（化合物35，LY255283）。使用抑制特异性[3H] LTB4与人PMN结合的测定方法，我们发现活性需要5位非极性取代基的取代。最佳活性是通过3位氢，2位羟基，1位短链烷基酮以及将4位氧与不饱和末端相连的六碳或八碳链实现的功能。选择在结合试验中IC50为87 nM的化合物35进行进一步的临床前评估。

  DOI：

  10.1021/jm00088a018
• 作为产物：
  描述：

  3,5-dimethoxy-2-valeryl-benzoic acid 在 喹啉 、 铜 作用下， 生成 1-(2,4-dimethoxyphenyl)pentan-1-one
  参考文献：
  名称：

  Nogami, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 46,50; dtsch. Ref. S. 21, 23

  摘要：

  DOI：

文献信息

• <i>p</i>-Selective (sp²)-C–H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
  作者：Ganesh Pandey、Sandip Kumar Tiwari、Bhawana Singh、Kumar Vanka、Shailja Jain

  DOI：10.1039/c7cc07529d

  日期：——

  p-Selective (sp2)-C-H functionalization of electron rich arenes have been achieved for acylation and alkylation reaction, respectively, with acyl/alkylselenides by organic photoredox catalysis involving interesting mechanistic pathway.

  富电子芳烃的p-选择性（sp2）-CH功能化已通过涉及有趣机理的有机光氧化还原催化分别通过酰基/烷基硒化物进行酰化和烷基化反应。
• [EN] ALPHA-AMINO BORONIC ACID DERIVATIVES, SELECTIVE IMMUNOPROTEASOME INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE ALPHA-AMINO BORONIQUE, INHIBITEURS SÉLECTIFS DE L'IMMUNOPROTÉASOME
  申请人：ARES TRADING SA

  公开号：WO2013092979A1

  公开（公告）日：2013-06-27

  The present invention provides compounds of Formula (I) as inhibitors of LMP7 for the treatment of autoimmune and inflammatory diseases. In formula (I), Rb and Rc are independently selected from one another from H or C1-C6-alkyl; whereby Rb and Rc may be linked to form a 5 or 6 membered-ring containing the oxygen atoms to which they are linked; Q denotes Ar, Het or cycloalkyl; R1 R2 independently from each other denotes H, ORa, Hal, C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; Y denotes CR 3R4, preferably CH2 or C(CH3)2; R 3, R4 independently of one another denote H or C1-C6-alkyl; L denotes L1 or L2 or alkyl; n is an integer selected from 0 to 3; L 1 is Q1-CO-M- wherein Q 1 is Ar or Het, preferably, phenyl, naphthyl or pyridine, optionally substituted with 1 to 5 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; L2 is Q2-M- wherein Q 2 is a fused bicyclic system containing 1 nitrogen atom and 1 to 3 additional groups independently selected from O, S, N, or CO, and wherein at least one of the rings is aromatic whereby the fused bicyclic system is optionally substituted with 1 to 5 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; or Q 2 is unsaturated or aromatic 5 membered-ring system containing 1 to 3 heteroatoms selected from N, O, S and CO, and optionally substituted with a phenyl ring or pyridine ring whereby phenyl ring and pyridine ring are optionally substituted with 1 to 4 groups independently selected from ORa, Hal, phenyl, and C1-C6-alkyl wherein 1 to 5 H atoms may be independently replaced by OH or Hal; M is a linear or branched alkylene having 1 to 5 carbon atoms wherein 1 or 2 H atoms may be replaced by OR a or a phenyl ring optionally substituted with 1 to 5 groups independently selected from Hal, ORa, and C1-C6-alkyl optionally substituted with 1 to 5 groups independently selected from OH, and Hal; or M denotes a cycloalkylene having 3 to 7 carbon atoms; or M denotes a thiazolidinyl group; R a is H or C1-C6-alkyl wherein 1 to 5 H atom may be independently replaced by OH or Hal; Ar denotes a 6 membered-aromatic carbocyclic ring optionally fused with another carbocyclic saturated, unsaturated or aromatic ring having 5 to 8 carbon atoms; Het denotes a 5- or 6-membered saturated, unsaturated or aromatic heterocyclic ring having 1 to 3 heteroatoms independently selected from N, N+O-, O, S, SO, and SO 2, and optionally fused with another saturated, unsaturated or aromatic ring having 5 to 8 atoms and optionally containing 1 to 3 heteroatoms selected from N, O, and S; Hal denotes CI, Br, I of F; preferably CI or F.

  本发明提供了化合物的公式（I）作为LMP7的抑制剂，用于治疗自身免疫和炎症性疾病。在公式（I）中，Rb和Rc分别独立地从H或C1-C6-烷基中选择；其中Rb和Rc可以连接形成一个含有它们连接的氧原子的5或6元环；Q表示Ar，Het或环烷基；R1和R2彼此独立地表示H，ORa，Hal，C1-C6-烷基，其中1到5个H原子可以独立地被OH或Hal替换；Y表示CR 3R4，优选CH2或C(CH3)2；R3，R4彼此独立地表示H或C1-C6-烷基；L表示L1或L2或烷基；n是从0到3选择的整数；L1是Q1-CO-M-，其中Q1是Ar或Het，优选苯基，萘基或吡啶基，可选地取代为1到5个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；L2是Q2-M-，其中Q2是含有1个氮原子和1到3个额外基团的融合双环系统，独立选择自O，S，N或CO，其中至少一个环是芳香环，融合双环系统可选地取代为1到5个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；或Q2是不饱和或芳香的含有1到3个从N，O，S和CO中选择的杂原子的5元环系统，并可选地取代为苯环或吡啶环，其中苯环和吡啶环可选地取代为1到4个从ORa，Hal，苯基和C1-C6-烷基中独立选择的基团，其中1到5个H原子可以独立地被OH或Hal替换；M是具有1到5个碳原子的线性或支链烷基，其中1或2个H原子可以被ORa或可选地取代为1到5个从Hal，ORa和C1-C6-烷基中独立选择的基团，可选地取代为1到5个从OH和Hal中独立选择的基团；或M表示具有3到7个碳原子的环烷基；或M表示噻唑烷基；Ra是H或C1-C6-烷基，其中1到5个H原子可以独立地被OH或Hal替换；Ar表示一个6元芳香碳环，可选地与另一个含有5到8个碳原子的碳环饱和、不饱和或芳香环融合；Het表示一个含有1到3个从N，N+O-，O，S，SO和SO2中独立选择的杂原子的5或6元饱和、不饱和或芳香杂环，可选地与另一个含有5到8个原子的饱和、不饱和或芳香环融合，并可选地含有1到3个从N，O和S中选择的杂原子；Hal表示CI，Br，I或F；优选CI或F。
• Metal-Free Intermolecular Coupling of Arenes with Secondary Amides: Chemoselective Synthesis of Aromatic Ketimines and Ketones, and <i>N</i>-Deacylation of Secondary Amides
  作者：Pei-Qiang Huang、Ying-Hong Huang、Kai-Jiong Xiao

  DOI：10.1021/acs.joc.6b01647

  日期：2016.10.7

  The direct transformation of common secondary amides into aromatic ketimines and aromatic ketones with C–C bond formation is described. The reaction can also be used for N-deacylation of secondary amides to release amines. This method consists of in situ amide activation with triflic anhydride and intermolecular capture of the resulting highly electrophilic nitrilium intermediate with an arene. The

  描述了将普通仲酰胺直接转化为具有C–C键的芳族酮亚胺和芳族酮的方法。该反应也可以用于仲酰胺的N-脱酰以释放胺。该方法包括原位用三氟甲磺酸酰胺活化酰胺，并用芳烃在分子间捕获所得的高度亲电的腈中间体。该反应适用于各种仲酰胺（亲电子试剂），但是仅富电子和中等富电子的芳烃可以用作亲核试剂。由于使用了台式稳定的芳烃而不是反应性和碱性有机金属作为亲核试剂，因此在存在一系列敏感官能团（例如醛，酮，酯，氰基，硝基，和三级酰胺基。该反应可以看作是使用仲酰胺作为酰化剂的Friedel-Crafts型反应，或者是Bischler-Napieralski反应的分子间形式。
• Multiple remote C(sp³)–H functionalizations of aliphatic ketones <i>via</i> bimetallic Cu–Pd catalyzed successive dehydrogenation
  作者：Hongyi Li、Chang Yin、Sien Liu、Hua Tu、Ping Lin、Jing Chen、Weiping Su

  DOI：10.1039/d2sc05370e

  日期：——

  The dehydrogenation-triggered multiple C(sp3)–H functionalizations at remote positions γ, δ or ε, ζ to carbonyl groups of aliphatic ketones with aryl/alkenyl carboxylic acids as coupling partners have been achieved using a bimetallic Cu–Pd catalyst system. This reaction allows access to alkenylated isocoumarins and their derivatives in generally good yields with high functional group tolerance. The

  使用双金属 Cu-Pd 催化剂体系，以芳基/烯基羧酸为偶联伙伴，在远程位置 γ、δ 或 ε、ze 上脱氢触发多个 C(sp 3 )–H 官能化为脂肪酮的羰基。该反应可以以通常良好的收率和高官能团耐受性获得烯基化异香豆素及其衍生物。双金属Cu-Pd协同催化对脂肪酮的高效连续脱氢的鉴定，克服了脂肪酮中末端未取代烷基链连续脱氢去饱和所带来的长期挑战，对于实现这种双金属Cu-Pd催化脱氢至关重要偶联反应。
• Nogami, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 46,50; dtsch. Ref. S. 21, 23
  作者：Nogami

  DOI：——

  日期：——