(E)-4-(4-(hydroxymethyl)phenyl)but-3-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(4-(hydroxymethyl)phenyl)but-3-en-2-one
• 英文别名: (E)-4-(3-oxobut-1-enyl)benzaldehyde；4-(3-oxobut-1-enyl)benzaldehyde；4-[(1E)-3-oxobut-1-en-1-yl]benzaldehyde；4-[(E)-3-oxobut-1-enyl]benzaldehyde
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: KSZRTQLIIKKDPN-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-formyl-N-methoxy-N-methylbenzamide 在 三氟甲磺酸三甲基硅酯 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.5h， 生成 (E)-4-(4-(hydroxymethyl)phenyl)but-3-en-2-one
  参考文献：
  名称：

  Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B

  摘要：

  Enones selectively react with a combination of PPh3 and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.

  DOI：

  10.1021/ol501463p

文献信息

• [EN] HYDROXAMATE-BASED INHIBITORS OF DEACETYLASES<br/>[FR] COMPOSÉS À BASE D'HYDROXAMATE EN TANT QU'INHIBITEURS DES DÉSACÉTYLASES
  申请人：NOVARTIS AG

  公开号：WO2012025164A1

  公开（公告）日：2012-03-01

  The present teachings relate to compounds of Formula (I): and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R1, R2, R3, R4, R5, ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula (I) and methods of use compounds of Formula (I) in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本教导涉及公式（I）的化合物及其药用盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z如本文所定义。本教导还提供制备公式（I）化合物的方法，以及利用公式（I）化合物治疗完全或部分由脱乙酰酶介导的病理状况或疾病的方法。
• Hydroxamate-Based Inhibitors of Deacetylases
  申请人：BROOKS Clinton A.

  公开号：US20110060009A1

  公开（公告）日：2011-03-10

  The present teachings relate to compounds of Formula I: and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula I and methods of use compounds of Formula I in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本教导涉及Formula I的化合物：及其药用盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z的定义如本文所述。本教导还提供制备Formula I化合物的方法，以及利用Formula I化合物治疗完全或部分由去乙酰酶介导的病理状况或疾病的方法。
• Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles
  作者：Song-Lin Zhang、Zhu-Qin Deng

  DOI：10.1039/c6ob01198e

  日期：——

  Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine

  报道了铜催化的β-羟基酮或腈与醛的转移醇醛式反应，这使得化学和立体选择性地接近（E）-α，β-不饱和酮和（E）-丙烯腈。建议原位铜（I）促进β-羟基酮或腈的逆向羟醛缩合反应的关键步骤，以生成反应性铜（I）烯醇盐或氰甲基中间体，随后发生醛缩醛与醛缩合以生成产物。该反应在6.0 mol％NaO t存在下，使用1.2 mol％Cu（IPr）Cl（IPr表示1,3-双（2,6-二异丙基苯基）咪唑-2-亚烷基）作为催化剂Bu助催化剂在室温或70°C下。一系列的芳基和杂芳基醛以及丙烯醛与可耐受的许多有用的官能团相容。在温和的弱碱性条件下，苯甲醛的竞争性Cannizzaro型反应和碱敏感官能团的副反应可以得到有效抑制，与经典的羟醛反应相比，该反应具有合成优势。该反应的合成潜力通过具有极高收率（高达91％）的生物活性喹啉和1,8-萘啶的一步合成得到了进一步证明。最后，在逆醛醇/醛醇两阶段机理的背景下，使用
• ENZYME INHIBITORS
  申请人：Donald Alastair David Graham

  公开号：US20120149736A1

  公开（公告）日：2012-06-14

  Compounds of formula (I), inhibit HDAC activity: wherein A, B and D independently represent ═CH— or ═N—; W is —CH═CH— Or —CH 2 CH 2 —; R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intra-cellular carboxylesterase enzymes to a carboxylic acid group; R2 and R3 are selected from the side chains of a natural or non-nat-ural alpha amino acid, provided that neither R2 nor R3 is hydrogen, or R2 and R3, taken together with the carbon to which they are attached, form a 3-6 membered saturated cycloalkyl or heterocyclyl ring; Y is a bond, —C(═O)—, —S(═O)2—, —C(═O)O—, —C(═O)NR′—, —C(═5)—NR′, —C(═NH)NR′ or —S(═O) 2 NR — wherein R′ is hydrogen or optionally substituted C 1 —C 6 alkyl; L 1 is a divalent radical of formula —(Alk 1 ) m ,(Q) n (Alk 2 ) p — wherein m, n, p, Q, Alk 1 and Alk 2 are as defined in the claims; X 1 represents a bond; —C(═O); or —S(═O) 2 —; —NR 4 C(═O)—, —C(═O)NR 4 —,— NR 4 C(═O)NR 5 —, —NR 4 S(═O) 2 —, or —S(═O) 2 NR 4 — wherein R4 and R5 are independently hydrogen or optionally substituted C 1 -C 6 alkyl; and z is 0 or 1.

  化合物的化学式（I），抑制HDAC活性：其中A、B和D分别表示═CH—或═N—; W是—CH═CH—或—CH2CH2—; R1是羧酸基（—COOH）或一个酯基，该酯基可被一个或多个细胞内羧酸酯酶水解成羧酸基; R2和R3是从天然或非天然α氨基酸的侧链中选择的，但R2和R3都不是氢，或R2和R3与它们所连接的碳一起形成3-6个成员的饱和环烷基或杂环基; Y是一个键，—C（═O）—，—S（═O）2—，—C（═O）O—，—C（═O）NR′—，—C（═5）—NR′，—C（═NH）NR′或—S（═O）2NR—，其中R′是氢或可选取代的C1-C6烷基; L1是具有公式—（Alk1）m，（Q）n（Alk2）p的二价基团，其中m、n、p、Q、Alk1和Alk2如权利要求中所定义; X1表示一个键;—C（═O）;或—S（═O）2—;—NR4C（═O）—，—C（═O）NR4—，—NR4C（═O）NR5—，—NR4S（═O）2—或—S（═O）2NR4—其中R4和R5独立地是氢或可选取代的C1-C6烷基; z为0或1。
• HYDROXAMATE-BASED INHIBITORS OF DEACETYLASES
  申请人：Brooks Clinton Alan

  公开号：US20130231373A1

  公开（公告）日：2013-09-05

  The present teachings relate to compounds of Formula (I): and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , ring A, and Z are as defined herein. The present teachings also provide methods of preparing compounds of Formula (I) and methods of use compounds of Formula (I) in treating pathologic conditions or disorders mediated wholly or in part by deacetylases.

  本发明涉及公式（I）化合物及其药学上可接受的盐、水合物、酯和前药，其中R1、R2、R3、R4、R5、环A和Z的定义如本文所述。本发明还提供制备公式（I）化合物的方法，以及使用公式（I）化合物治疗完全或部分通过去乙酰化酶介导的病理条件或疾病的方法。