3-(4-hydroxyphenyl)-2-ethoxycarbonyl-propionic acid ethyl ester | 77094-90-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(4-hydroxyphenyl)-2-ethoxycarbonyl-propionic acid ethyl ester
• 英文别名: (p-hydroxybenzyl)-malonic acid,diethyl ester；(p-hydroxybenzyl) malonic acid, diethyl ester；Propanedioic acid, [(4-hydroxyphenyl)methyl]-, diethyl ester；diethyl 2-[(4-hydroxyphenyl)methyl]propanedioate
• CAS: 77094-90-7
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: WQZQTEDGHBZZOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-2-ethoxycarbonyl-propionic acid ethyl ester 在 Pearlman's catalyst sodium hydroxide 、 18-冠醚-6 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  The β-glucuronyl-based prodrug strategy allows for its application on β-glucuronyl-platinum conjugates

  摘要：

  The use of platinum drugs in antitumour therapy is well established. An important drawback of these chemotherapeutics is the lack of selectivity for tumour cells, usually resulting in severe toxic side effects. A glucuronyl-platinum conjugate was designed and synthesised to test the compatibility of platinum compounds with beta-glucuronidase-based prodrug therapy. Instantaneous cleavage of the beta-glucuronic bond in the glucuronyl-platinum conjugate was observed upon addition of beta-glucuronidase resulting in Pt-II(dach)(4-hydroxybenzylmalonate) and glucuronic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.015
• 作为产物：
  描述：

  4-benzoyloxybenzyl bromide 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 3-(4-hydroxyphenyl)-2-ethoxycarbonyl-propionic acid ethyl ester
  参考文献：
  名称：

  The β-glucuronyl-based prodrug strategy allows for its application on β-glucuronyl-platinum conjugates

  摘要：

  The use of platinum drugs in antitumour therapy is well established. An important drawback of these chemotherapeutics is the lack of selectivity for tumour cells, usually resulting in severe toxic side effects. A glucuronyl-platinum conjugate was designed and synthesised to test the compatibility of platinum compounds with beta-glucuronidase-based prodrug therapy. Instantaneous cleavage of the beta-glucuronic bond in the glucuronyl-platinum conjugate was observed upon addition of beta-glucuronidase resulting in Pt-II(dach)(4-hydroxybenzylmalonate) and glucuronic acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.015

文献信息

• Reactivity of new precursors of quinone methides
  作者：Bernard Loubinoux、Joseph Miazimbakana、Philippe Gerardin

  DOI：10.1016/s0040-4039(00)99619-9

  日期：1989.1

  The azidomethylene protecting group allows the synthesis of unstable phenolic compounds which are used as quinone methide precursors in the alkylations of alcohols, phenols, azide, thiophenol, amines, enols and enolates.

  叠氮基亚甲基保护基团允许合成不稳定的酚类化合物，在醇，酚，叠氮化物，硫酚，胺，烯醇和烯醇化物的烷基化中用作醌甲基化物前体。
• A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides
  作者：Yin Zheng、Suihan Zhang、Kam-Hung Low、Weiwei Zi、Zhongxing Huang

  DOI：10.1021/jacs.1c12404

  日期：2022.2.2

  can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access

  对映体富集的叔烷基卤化物普遍存在于生物活性分子中，可作为通用合成中间体来构建复杂结构。虽然常规获得这些基序通常取决于立体选择性碳-卤素或碳-碳键形成反应，但相比之下，使用卤代和前手性四取代碳的不对称方法在很大程度上难以捉摸。在这里，我们报告了一套具有脯氨醇或哌啶醇衍生的四齿配体的双核锌催化剂可以将大量容易获得的卤代丙二酸酯还原为α-卤代-β-羟基酯。这些多官能化的叔烷基氟化物、氯化物和溴化物被证明是氟化药物类似物和多卤化单萜的有用中间体。
• Aminobenzoic and aminocyclohexane-carboylic acid compounds, compositions, and their method of use
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0361365A1

  公开（公告）日：1990-04-04

  Compounds of the formula wherein X is inhibit the action of neutral endopeptidase. As a result, such compounds produce diuresis, natriuresis, and lower blood pressure as well as being useful in the treatment of congestive heart failure, relieving pain, and diarrhea when administered to a mammalian host.

  其中X的化合物抑制中性内肽酶的作用。因此，这些化合物产生利尿、排钠和降低血压的效果，同时在治疗充血性心力衰竭、缓解疼痛和腹泻时对哺乳动物宿主有用。
• Malonic acid derivatives and methods for their synthesis
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0254080A2

  公开（公告）日：1988-01-27

  The present invention refers to a new class of malonic acid derivatives of general formula I wherein R¹ and R², each independently, represent hydrogen or a carboxyl protecting group, and the residue R corresponds to the side-chain of the amino acids lysine, ornithine, tyrosine, cysteine, aspartic acid and glutamic acid wherein the additional functionalities are suitably protected. The new compounds of the present invention are useful for preparing analogues of biologically active peptides wherein the direction of some amide bonds in which the amino acids lysine, ornithine, tyrosine, cysteine, aspartic acid or glutamic acid are involved, has been reversed.

  本发明涉及一类新的丙二酸衍生物，其通式为 I 其中R¹和R²各自独立地代表氢或羧基保护基团，残基R对应于氨基酸赖氨酸、鸟氨酸、酪氨酸、半胱氨酸、天冬氨酸和谷氨酸的侧链，其中附加官能团受到适当保护。 本发明的新化合物可用于制备生物活性肽的类似物，其中赖氨酸、鸟氨酸、酪氨酸、半胱氨酸、天门冬氨酸或谷氨酸参与的某些酰胺键的方向已被逆转。
• Toll-like receptor 2 antagonists. Part 1: Preliminary SAR investigation of novel synthetic phospholipids
  作者：Mark R. Spyvee、Huiming Zhang、Lynn D. Hawkins、Jesse C. Chow

  DOI：10.1016/j.bmcl.2005.08.080

  日期：2005.12

  Novel synthetic phospholipid compound I was discovered to be an antagonist of human toll-like receptor 2 (TLR2) signaling. In a preliminary SAR campaign we synthesized several analogues of 1 and found that considerable structural changes could be made without loss of TLR2 antagonistic activity. (c) 2005 Elsevier Ltd. All rights reserved.