phenacyl 4-(hydroxymethyl)benzoate | 136581-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenacyl 4-(hydroxymethyl)benzoate
• 英文别名: 2-Oxo-2-phenylethyl 4-(hydroxymethyl)benzoate
• CAS: 136581-11-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: DNIZDXQRAOZBFN-UHFFFAOYSA-N

物化性质

• 沸点：
  485.5±35.0 °C(predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenacyl 4-(hydroxymethyl)benzoate 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]oxymethyl]benzoic acid
  参考文献：
  名称：

  Simultaneous Multiple Synthesis of Peptide Amides by the Multipin Method. Application of Vapor-Phase Ammonolysis

  摘要：

  A method for simultaneously preparing large numbers of peptide amides is described. Side-chain deprotected, support-bound peptide esters 1 and 2 are incubated with ammonia/tetrahydrofuran vapor. The cleaved peptide amides 3 are then eluted from the support with a solvent of choice. The approach is demonstrated in conjunction with the multipin method of multiple peptide synthesis. In this study, chromophoric model systems of support-bound 4-(oxymethyl)benzamido esters of the genetically coded amino acids (except Cys) 4 and glycolamido esters of Ile, Val and Pro 5 were cleaved using the vapor from solutions of 30% ammonia in tetrahydrofuran) methanol, and 2-propanol. The best yields were obtained with 30% ammonia in tetrahydrofuran. When methanol was used as cosolvent, the amide products were contaminated with methyl ester. When ammonia gas alone was used, very poor yields were recorded. Although the hindered amino acid esters 4(Ile, Val, Pro) cleaved with poor efficiency, the corresponding glycolamido esters S(Ile, Val, Pro) cleaved with >90% efficiency upon treatment with ammonia/tetrahydofuran vapor. Racemization studies on a : selection of dipeptides cleaved by the method demonstrated that only low levels of racemate were generated. Four test peptides 16-19 were prepared and characterized to demonstrate the general utility of the method. The approach gives ready access to hundreds to thousands of discrete peptide amides in quantities (10-100 nmol) sufficient for most biological, immunological, and pharmacological studies.

  DOI：

  10.1021/jo00087a041
• 作为产物：
  描述：

  4-羟甲基苯甲酸 、 2-溴苯乙酮 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 64.0h， 以81%的产率得到phenacyl 4-(hydroxymethyl)benzoate
  参考文献：
  名称：

  Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis

  摘要：

  A method of simultaneous multiple peptide synthesis which integrates synthesis, side-chain deprotection, cleavage, and purification so as to afford peptide solutions suitable for immediate biological testing is described. The approach utilizes a novel diketopiperazine-forming cleavable linker 1. Upon side-chain deprotection, 1 gives 2, which is stable to a protocol designed to remove contaminants from the support-bound peptide prior to cleavage. Peptide cleavage is then effected by treating 2 with a neutral or near neutral buffer to give peptide 4, which carries a C-terminal diketopiperazine moiety, in good yield. In this study the glycolamido and 4-(oxymethyl)benzamido esters of 1 have been appraised. The approach is demonstrated in model studies on 7 and 8 and in the preparation and characterization of peptides 17-21. The general approach allows 10-100-nmol quantities of many hundreds of peptides to be concurrently prepared in a relatively short period of time when used in conjunction with the multipin method of multiple peptide synthesis.

  DOI：

  10.1021/jo00023a035

文献信息

• [EN] PYRIDINE COMPOUNDS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE IV<br/>[FR] COMPOSES PYRIDINES UTILISES COMME INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005042488A1

  公开（公告）日：2005-05-12

  A compound represented by the formula wherein R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R3 is an optionally substituted aromatic group; R4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式表示为其中R1和R2相同或不同，每个都是可选择取代的碳氢基团或可选择取代的羟基团；R3是可选择取代的芳香基团；R4是可选择取代的氨基团；L是二价链状碳氢基团；Q是键或二价链状碳氢基团；X是氢原子、氰基、硝基、酰基、取代的羟基团、可选择取代的硫醇基团、可选择取代的氨基团或可选择取代的环状基团；但当X是乙氧羰基团时，Q为二价链状碳氢基团。该化合物具有肽酶抑制作用，可用作糖尿病等疾病的预防或治疗药物，并在功效、作用持续时间、特异性、毒性较低等方面具有优越性。
• Pyridine compounds as inhibitors of dipeptidyl peptidase IV
  申请人：Oi Satoru

  公开号：US20070037807A1

  公开（公告）日：2007-02-15

  A compound represented by the formula wherein R 1 and R 2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R 3 is an optionally substituted aromatic group; R 4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式为其中R1和R2是相同或不同的可选择取代的烃基或可选择取代的羟基；R3是可选择取代的芳香基；R4是可选择取代的氨基；L是二价链烃基；Q是键或二价链烃基；X是氢原子、氰基、硝基、酰基、可选择取代的羟基、可选择取代的硫醇基、可选择取代的氨基或可选择取代的环状基；但当X是乙氧羰基时，Q是二价链烃基。该化合物具有肽酶抑制作用，可用作预防或治疗糖尿病等药物，具有优异的疗效、持续时间、特异性、低毒性等特点。
• PYRIDINE COMPOUNDS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE IV
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1678138A1

  公开（公告）日：2006-07-12
• CN115974758
  申请人：——

  公开号：——

  公开（公告）日：——
• Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis
  作者：Andrew M. Bray、N. Joe Maeji、Robert M. Valerio、Rhonda A. Campbell、H. Mario Geysen

  DOI：10.1021/jo00023a035

  日期：1991.11

  A method of simultaneous multiple peptide synthesis which integrates synthesis, side-chain deprotection, cleavage, and purification so as to afford peptide solutions suitable for immediate biological testing is described. The approach utilizes a novel diketopiperazine-forming cleavable linker 1. Upon side-chain deprotection, 1 gives 2, which is stable to a protocol designed to remove contaminants from the support-bound peptide prior to cleavage. Peptide cleavage is then effected by treating 2 with a neutral or near neutral buffer to give peptide 4, which carries a C-terminal diketopiperazine moiety, in good yield. In this study the glycolamido and 4-(oxymethyl)benzamido esters of 1 have been appraised. The approach is demonstrated in model studies on 7 and 8 and in the preparation and characterization of peptides 17-21. The general approach allows 10-100-nmol quantities of many hundreds of peptides to be concurrently prepared in a relatively short period of time when used in conjunction with the multipin method of multiple peptide synthesis.