methyl 4-(phenethylcarbamoyl)benzoate

• 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: methyl 4-(phenethylcarbamoyl)benzoate
• 英文别名: Methyl 4-(2-phenylethylaminocarbonyl)benzoate；methyl 4-(2-phenylethylcarbamoyl)benzoate
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: AZJUYXNPKUTNIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(phenethylcarbamoyl)benzoate 在 羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 N-hydroxy-N'-phenethyl-terephthalamide
  参考文献：
  名称：

  Potent and Selective Inhibition of Histone Deacetylase 6 (HDAC6) Does Not Require a Surface-Binding Motif

  摘要：

  Hydroxamic acids were designed, synthesized, and evaluated for their ability to selectively inhibit human histone deacetylase 6 (HDAC6). Several inhibitors, including compound 14 (BRD9757), exhibited excellent potency and selectivity despite the absence of a surface-binding motif. The binding of these highly efficient ligands for HDAC6 is rationalized via structure-activity relationships. These results demonstrate that high selectivity and potent inhibition of HDAC6 can be achieved through careful choice of linker element only.

  DOI：

  10.1021/jm301355j
• 作为产物：
  描述：

  tert-butyl ((diethylcarbamoyl)oxy)(phenethyl)carbamate 在 三氟乙酸 、 柠檬酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.25h， 生成 methyl 4-(phenethylcarbamoyl)benzoate
  参考文献：
  名称：

  水性条件下酰基硅烷和羟胺之间的化学选择性形成酰胺的连接

  摘要：

  我们报道了在水性条件下酰基硅烷与羟胺的酰胺形成反应（ASHA连接）。结扎快速，化学选择性，温和，高产，并具有出色的功能组耐受性。一系列市售药物，多肽，天然产物和生物活性化合物的后期修饰显示了反应的鲁棒性和功能基团耐受性。反应成功的关键可能是通过布鲁克型重排可能形成牢固的Si-O键。鉴于其简单性和高效性，这种连接方法有潜力在药物化学和化学生物学领域中展现出新的应用。

  DOI：

  10.1002/anie.202012459

文献信息

• Direct oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process
  作者：Renzhong Fu、Yang Yang、Jin Zhang、Jintao Shao、Xuming Xia、Yunsheng Ma、Rongxin Yuan

  DOI：10.1039/c5ob02376a

  日期：——

  A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights

  已经报道了一种简单有效的方法，可在无溶剂条件下直接由杂多阴离子型离子液体催化的醛和胺直接合成酰胺。发现该实用方案可耐受具有不同官能团的多种底物。主要亮点是中等至出色的产量，无溶剂介质和操作简便。简要研究了所提出的双重催化机理。此外，基于杂多阴离子的离子液体易于用于该氧化酰胺化。
• An efficient, eco-friendly and sustainable tandem oxidative amidation of alcohols with amines catalyzed by heteropolyanion-based ionic liquids via a bifunctional catalysis process
  作者：Renzhong Fu、Yang Yang、Wei Feng、Qiuxia Ge、Yan Feng、Xiaojun Zeng、Wen Chai、Jun Yi、Rongxin Yuan

  DOI：10.1016/j.tet.2016.11.002

  日期：2016.12

  eco-friendly and sustainable method for the tandem oxidative amidation of alcohols with amines has been reported. Using heteropolyanion-based ionic liquids as the catalyst and tert-butyl hydroperoxide as the oxidant, this amidation reaction is operationally straightforward and provides a series of primary, secondary and tertiary amides derivatives in moderate to good yields. Solvent-free media, microwave-promoted

  已经报道了一种有效的，生态友好的和可持续的方法，用于醇与胺的串联氧化酰胺化。使用基于杂多阴离子的离子液体作为催化剂，使用叔丁基氢过氧化物作为氧化剂，该酰胺化反应操作简单，并以中等至良好的产率提供了一系列伯，仲和叔酰胺衍生物。无溶剂介质，微波促进条件和催化剂的可重复使用性是主要亮点。此外，在本报告中已对所提出的双功能催化机理进行了简要研究。
• Iron-catalysed oxidative amidation of alcohols with amines
  作者：Silvia Gaspa、Andrea Porcheddu、Lidia De Luca

  DOI：10.1039/c3ob40170g

  日期：——

  A new iron-catalysed oxidative amidation of differently substituted benzylic alcohols with mono- and di-substituted amines was developed.

  开发了一种新的铁催化氧化酰胺化不同取代的苄醇与单-和二-取代胺的方法。
• Substituted 3,4-dihydroxy-phenylethylamino compounds
  申请人：Fisons, plc

  公开号：US04720586A1

  公开（公告）日：1988-01-19

  There are provided compounds of formula I, ##STR1## in which R.sub.1 represents OH, R.sub.2 and R.sub.3, which may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, alkyl C1 to 6, nitro, nitrile, (CH.sub.2).sub.p R.sub.9 or SR.sub.9, W represents a single bond, a 1,2; 1,3; or 1,4-disubstituted benzene ring; a --CH.dbd.CH--group or a 1,4-cyclohexanediyl group; X respresents NH, O, S, SO.sub.2, CO, CH.sub.2, CONH or --COO; Y represents (CH.sub.2)q, CO, CS, SO.sub.2 and R.sub.20 represents hydrogen, or Y represents CR.sub.15 R.sub.16 CR.sub.17 R.sub.18, wherein the carbon atom bearing R.sub.15 and R.sub.16 is adjacent to X and in which R.sub.15 and R.sub.18, together with the carbon atom to which they are attached form a carbonyl group, and R.sub.15, R.sub.16 and R.sub.20 each represent hydrogen, or R.sub.15 and R.sub.20 together form a chain --CH.sub.2 --, and R.sub.16, R.sub.17 and R.sub.18 each represent hydrogen, or R.sub.15, R.sub.16, R.sub.17 and R.sub.18 each independently represent hydrogen or alkyl C1 to 6 and R.sub.20 represents hydrogen; Z represents a single bond, NR.sub.19, CH.sub.2, O, CO, S or SO.sub.2, in which R.sub.19 represents hydrogen or alkyl C1 to 6; n, and m each independently represent an integer from 1 to 4 inclusive; q represents an integer from 1 to 3 inclusive; p represents 0 or an integer from 1 to 3 inclusive; R.sub.9 represents phenyl or phenyl substituted by hydroxy, and R.sub.10 represents hydrogen or chlorine, provided that (i) when R.sub.1 represents --OH, R.sub.2 and R.sub.3 both represent hydrogen, X represents NH, Y represents (CH.sub.2).sub.q, Z represents a single bond and R.sub.20 represents hydrogen, W does not represent a single bond; (ii) when R.sub.1 represents --OH, R.sub.2 and R.sub.3 both represent hydrogen, W represents a single bond, X represents NH and Z represents a single bond, then at least one of R.sub.15, R.sub.16, R.sub.17 and R.sub.18 is alkyl C1 to 6; (iii) when X represents SO.sub.2, CO, COO or CONH, then Y does not represent CO, CS or SO.sub.2 ; (iv) when Y represents CO, CS or SO.sub.2, then Z does not represent CO or SO.sub.2, and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

  提供了化合物I的公式，其中R.sub.1代表OH，R.sub.2和R.sub.3可以相同或不同，各自独立地代表氢，氟，氯，溴，烷基C1至6，硝基，腈基，（CH.sub.2）.sub.pR.sub.9或SR.sub.9，W代表单键，1,2; 1,3;或1,4-二取代苯环；-CH.dbd.CH-基团或1,4-环己基基团；X代表NH，O，S，SO.sub.2，CO，CH.sub.2，CONH或-COO；Y代表（CH.sub.2）q，CO，CS，SO.sub.2和R.sub.20代表氢，或Y代表CR.sub.15 R.sub.16 CR.sub.17 R.sub.18，其中带有R.sub.15和R.sub.16的碳原子邻接X，且R.sub.15和R.sub.18与它们附着的碳原子一起形成羰基基团，且R.sub.15，R.sub.16和R.sub.20各代表氢，或R.sub.15和R.sub.20一起形成链-CH.sub.2-，R.sub.16，R.sub.17和R.sub.18各代表氢，或R.sub.15，R.sub.16，R.sub.17和R.sub.18各自独立地代表氢或烷基C1至6，R.sub.20代表氢；Z代表单键，NR.sub.19，CH.sub.2，O，CO，S或SO.sub.2，其中R.sub.19代表氢或烷基C1至6；n和m各自独立地代表从1到4的整数，包括1和4；q代表从1到3的整数；p代表0或从1到3的整数；R.sub.9代表苯基或被羟基取代的苯基，R.sub.10代表氢或氯，但是当R.sub.1代表-OH时，R.sub.2和R.sub.3都代表氢，X代表NH，Y代表（CH.sub.2）.sub.q，Z代表单键，R.sub.20代表氢时，W不代表单键；当R.sub.1代表-OH时，R.sub.2和R.sub.3都代表氢，W代表单键，X代表NH，Z代表单键时，至少有一个R.sub.15，R.sub.16，R.sub.17和R.sub.18是烷基C1至6；当X代表SO.sub.2，CO，COO或CONH时，Y不代表CO，CS或SO.sub.2；当Y代表CO，CS或SO.sub.2时，Z不代表CO或SO.sub.2，且其药学上可接受的衍生物。还描述了将公式I的化合物用作制药物的用途，制备化合物和制药，例如心脏，含有化合物的组合物。
• Dihydroxy-phenethylamino compounds useful as pharmaceuticals
  申请人：Fisons, plc

  公开号：US04803225A1

  公开（公告）日：1989-02-07

  There are provided compounds of formula I, ##STR1## and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

  提供了公式I的化合物，##STR1##以及其药学上可接受的衍生物。还描述了公式I化合物作为药物的用途，制备化合物和制药方法，例如含有这些化合物的制药，如心脏组成物。