methyl O^α-benzoylglycolate | 29747-05-5

• 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 O^α-benzoylglycolate
• 英文别名: methyl O-benzoylglycolate；methyl benzoylglycolate；methyl 2-benzoyloxyacetate；2-Methoxy-2-oxoethyl benzoate；(2-methoxy-2-oxoethyl) benzoate
• CAS: 29747-05-5
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: XVBCLDIWVJJXTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl O^α-benzoylglycolate 在 溶剂黄146 作用下， 反应 4.0h， 生成 Benzoic acid 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromen-3-yl ester
  参考文献：
  名称：

  The synthesis and transformations of substituted 2-hydroxy-3-dimethylaminopropenoates. The preparation of condensed 3-hydroxypyran-2-ones

  摘要：

  A convenient synthesis of substituted 2-hydroxy-3-dimethylaminopropenoates is reported. They react with cyclic 1,3-diketones, with aromatic and heteroaromatic hydroxy compounds to afford the corresponding 3-substituted hydroxytetrahydro-2H-1-benzopyran-2-ones, benzo- and naphthopyran-2-ones and azolo- and azinopyran-2-ones, respectively. Catalytic debenzylation of 3-benzyloxy substituted fused pyran-2-ones gives free 3-hydroxy derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00534-1
• 作为产物：
  描述：

  (aminocarbonyl)methyl benzoate 在 盐酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.06h， 生成 methyl O^α-benzoylglycolate
  参考文献：
  名称：

  Thomas, H. Guenter; Kessel, Stephan, Chemische Berichte, 1985, vol. 118, # 7, p. 2777 - 2788

  摘要：

  DOI：

文献信息

• [EN] ENZYME INHIBITORS<br/>[FR] INHIBITEURS D'ENZYMES
  申请人：UNIV AUSTRALIAN

  公开号：WO2004007417A1

  公开（公告）日：2004-01-22

  A compound of Formula (I) wherein R is a biomolecular residue, or derivative thereof, of a C-terminal amide biomolecule which is activated by the action of PAM; and X is O or CH2 or a salt, or prodrug thereof.

  式（I）的化合物中，其中R是C-末端酰胺生物分子的生物分子残基或其衍生物，通过PAM的作用被激活；X是O或CH2或其盐或前药。
• Inhibition of Peptidylglycine α-Amidating Monooxygenase by Exploitation of Factors Affecting the Stability and Ease of Formation of Glycyl Radicals
  作者：Brendon J. W. Barratt、Christopher J. Easton、David J. Henry、Iris H. W. Li、Leo Radom、Jamie S. Simpson

  DOI：10.1021/ja046204n

  日期：2004.10.1

  Peptidylglycine alpha-amidating monooxygenase catalyzes the biosynthesis of peptide hormones through radical cleavage of the C-terminal glycine residues of the corresponding prohormones. We have correlated ab initio calculations of radical stabilization energies and studies of free radical brominations with the extent of catalysis displayed by peptidylglycine alpha-amidating monooxygenase, to identify

  肽基甘氨酸 α-酰胺化单加氧酶通过自由基切割相应激素原的 C 端甘氨酸残基来催化肽激素的生物合成。我们将自由基稳定能的从头计算和自由基溴化的研究与肽基甘氨酸 α-酰胺化单加氧酶显示的催化程度相关联，以确定酶抑制剂的类别。特别是我们发现，在密切相关的系统中，用甘氨酸取代乙醇酸使计算的自由基稳定能降低了 34.7 kJ mol(-1)，在四氯化碳中回流时用 N-溴代琥珀酰亚胺的溴化速率降低了一个因子至少 2000，并停止单加氧酶的催化作用，同时保持与酶的结合。
• Pyrimidine derivatives and processes for the preparation thereof
  申请人：Yuhan Corporation

  公开号：US06352993B1

  公开（公告）日：2002-03-05

  The present invention relates to novel pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing the same as an active ingredient, their novel intermediates, and processes for the preparation thereof wherein: when A is piperidin-1-yl or —NH—B, wherein B is C3-C4 alkyl, C3-C4 alkenyl, C3-C7 cycloalkyl, C1-C3 alkoxyethyl, phenylethl which may be substituted or unsubstituted, 3-trifluoromethylphenylmethyl, 1-naphthylmethyl, 4-methylthiazol-2-yl or 4-phenylthiazol-2-yl, R1 is hydrogen or methyl; and R2, R3, R4 and R5 are hydrogen; or when A is a group of formula (II); when R1 is hydroxymethyl or C1-C3 alkoxymethyl, R2, R3, R4, R5 and R6 are hydrogen; and R7 is hydrogen or halogen; or when R1 is hydrogen or methyl, R7 is hydrogen or halogen; and one or two of R2, R3, R4, R5 and R6 is hydroxy, methoxy, or a group of formula (III) wherein Z is C1-C4 alkyl, substituted or unsubstituted C1-C4 alkenyl, cyloalkyl, benzyloxyalkyl, alkoxycarbonylalkyl, morpholinomethyl, piperidinomethyl, 4-substituted-piperazinomethyl, substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted benzyl, thiophen-2-yl-methyl, 1-substituted-pyrrolidin-2-yl or —CHR8NHR9, wherein R8 is hydrogen, methyl, isopropyl, benzyl, benzyloxymethyl, methylthioethyl, benzyloxycarbonylmethyl, carbamolymethyl, carbamoylethyl, or 1-benzylimidazol-4-ylmethyl and R9 is hydrogen or t-butoxycarbonyl; and the others are hydrogen or methyl.

  本发明涉及具有优异抗分泌活性的新型嘧啶衍生物的化学式(I)或其药学上可接受的盐，以及含有其作为活性成分的药物组合物，其新型中间体，以及其制备方法，其中：当A为哌啶-1-基或-NH-B时，其中B为C3-C4烷基，C3-C4烯基，C3-C7环烷基，C1-C3烷氧乙基，苯乙基，可以是取代或未取代的，3-三氟甲基苯甲基，1-萘甲基，4-甲基噻唑-2-基或4-苯基噻唑-2-基，R1为氢或甲基；而R2、R3、R4和R5为氢；或当A为化学式(II)的基团时；当R1为羟甲基或C1-C3烷氧甲基，R2、R3、R4、R5和R6为氢；而R7为氢或卤素；或当R1为氢或甲基，R7为氢或卤素；且R2、R3、R4、R5和R6中的一个或两个为羟基，甲氧基，或化学式(III)的基团，其中Z为C1-C4烷基，取代或未取代的C1-C4烯基，环烷基，苄氧基烷基，烷氧羰基烷基，吗啉甲基，哌啶甲基，4-取代哌嗪甲基，取代或未取代的苯基，萘基，取代或未取代的苄基，噻吩-2-基-甲基，1-取代吡咯啉-2-基或-NHR9，其中R8为氢，甲基，异丙基，苄基，苄氧甲基，甲硫乙基，苄氧羰基甲基，氨基甲基，氨基乙基，或1-苄基咪唑-4-基甲基，而R9为氢或叔丁氧羰基；其他为氢或甲基。
• [EN] PRO-DRUG FORMING COMPOUNDS<br/>[FR] COMPOSÉS POUR LA FORMATION DE PROMÉDICAMENTS
  申请人：EVESTRA INC

  公开号：WO2015006691A1

  公开（公告）日：2015-01-15

  Various prodrug compounds having the general structure: Active agent- (acid)-(linker) - SO2NR1R2 are described herein. Compounds having this general structure were shown to be more orally active than the unmodified parent molecule.

  本文描述了具有以下一般结构的各种前药化合物：活性药物-（酸）-（连接物）-SO2NR1R2。具有这种一般结构的化合物被证明比未经修改的母体分子更适合口服给药。
• Practical one-pot sequence for the asymmetric synthesis of 1,2 diols from primary alcohols
  作者：Philippe Hermange、François Portalier、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetlet.2012.11.137

  日期：2013.2

  practical one-pot three-step sequence is reported for the asymmetric synthesis of α-benzoyloxylated alcohols from primary alcohols. Good overall yields (36–52%) and enantioselectivities (91–94% e.e.) are obtained using a commercial organocatalyst in the key oxylation reaction. A simple modification in the protocol allows the formation of enantioenriched γ-benzoyloxylated α,β-unsaturated ester from alcohol

  报道了从伯醇不对称合成α-苯甲酰氧基化醇的实际一锅三步程序。在关键的氧化反应中使用商业有机催化剂可获得良好的总收率（36-52％）和对映选择性（91-94％ee）。方案中的简单修改即可从醇中形成对映体富集的γ-苯甲酰氧基化的α，β-不饱和酯。已将合成实用程序用于从己-1-醇轻松制备（-）-γ-八内酯。