phenacyl glycolate | 133038-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenacyl glycolate
• 英文别名: hydroxy-acetic acid 2-oxo-2-phenyl-ethyl ester；phenacyl 2-hydroxyacetate
• CAS: 133038-43-4
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD30479317
• 分子量: 194.187
• InChiKey: YMMMFMKSPOHZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Fmoc-L-脯氨酸 、 phenacyl glycolate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到phenacyl (9-fluorenylmethoxycarbonyl)-L-prolylglycolate
  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
• 作为产物：
  描述：

  羟基乙酸 、 2-溴苯乙酮 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 phenacyl glycolate
  参考文献：
  名称：

  Ketone precursors for organoleptic compounds

  摘要：

  该发明公开了式I的酮化合物：其中，Y是可选择取代的烷基，环烷基或环烷基烷基，其中每个烷基是直链或支链的，每个烷基和环烷基基团是饱和或不饱和的；R1是氢或取代的C1-6烷基基团，饱和或不饱和的，直链或支链的；A是含色团取代的芳香环或环系；n是整数；且在式I不是2-乙氧基-1-苯基-乙酮的限制条件下。这些化合物对于传递感官化合物特别是香料、香料、掩蔽剂和抗菌化合物非常有用。

  公开号：

  US06258854B1

文献信息

• Ketones useful as precursors for organoleptic compounds
  申请人：Givaudan Roure (International) S.A.

  公开号：EP0983990A2

  公开（公告）日：2000-03-08

  The ketones of the formula I are useful for the delivery of organoleptic compounds, especially for flavours, fragrances and masking agents and antimicrobial compounds.

  式 I 中的酮类化合物可用于传递感官化合物，特别是香精、香料、掩蔽剂和抗菌化合物。
• 新規ケトン類
  申请人：——

  公开号：JP2000095718A

  公开（公告）日：2000-04-04

  (57)【要約】\n【課題】 感覚刺激性化合物の先駆体としての新規なケトンを提供すること。\n【解決手段】 式Ｉ\n【化１】\n［式中、Ｙ、Ｒ1、Ａ及びｎは明細書において定義した通りである］で示されるケトンであって、２−エトキシ−１−フェニル−エタノン、ヒドロキシ酢酸２−オキソ−２−フェニル−エチルエステル、酢酸１−メチル−２−オキソ−２−フェニル−エチルエステル及びｐ−メトキシフェナシルアセテートではない上記ケトン。

  (57) [摘要] Јn [问题] 提供一种新型酮作为感官刺激化合物的前体。\解] 式 IЈn 的酮 [式 1] Јn [其中 Y、R1、A 和 n 如说明书中定义]，2-乙氧基-1-苯基-乙酮、羟基乙酸 2-氧代-2-苯基-乙基酯、乙酸 1-甲基-2-氧代-2-苯基-乙基酯和上述酮类，但不包括对甲氧基苯乙酸酯。
• Simultaneous Multiple Synthesis of Peptide Amides by the Multipin Method. Application of Vapor-Phase Ammonolysis
  作者：Andrew M. Bray、Akhil G. Jhingran、Robert M. Valerio、N. Joe Maeji

  DOI：10.1021/jo00087a041

  日期：1994.4

  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.
• US6258854B1
  申请人：——

  公开号：US6258854B1

  公开（公告）日：2001-07-10