bis[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] butanedioate | 314069-31-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] butanedioate
• CAS: 314069-31-3
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: MGPVOUNUCYTFNG-ROUUACIJSA-N

物化性质

• 沸点：
  541.8±40.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] butanedioate 在 palladium on activated charcoal 氢气 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 25.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 生成 di(1S)-1-{[1-methyl-2-(2-methylprop-2-enoylamino) ethyl]oxycarbonyl}ethyl butane-1,4-dioate
  参考文献：
  名称：

  Oligo-α-hydroxy Ester Cross-Linkers:  Impact of Cross-Linker Structure on Biodegradable Hydrogel Networks

  摘要：

  We describe the synthesis of a series of biodegradable oligo-alpha-hydroxy ester cross-linkers and evaluate their impact on the degradation kinetics and macromolecule diffusion from a hydrogel network. By changing the steric and electronic environment at the site of degradation in the cross-linker, we were able to modulate the degradation, swelling kinetics, and corresponding release profiles of macromolecules from poly(HPMA) hydrogel networks under physiologically relevant conditions. As the steric hindrance and electron demand at the site of hydrolysis for three different cross-linkers was increased, the total time for the hydrogel network to completely dissolve increased from 2 to over 30 days while incubated in pH 7 buffer. As the number of hydrolyzable sites and the electron demand at the side of hydrolysis decreased, the time to completely dissolve decreased from weeks to several days. Increasing the cross-linking density for one of the degradable cross-linkers (1.5% to 3.0% feed ratio) increased the degradation time by several weeks. Burst release was absent for high molecular weight solutes because the release rate depended on controlled degradation of the polymer network and an increase in average network mesh size. The synthetically adaptable cross-linkers described herein offer a new approach for controlling the rate and extent of release from biodegradable hydrogel networks.

  DOI：

  10.1021/ma0518306
• 作为产物：
  描述：

  (S)-(-)-乳酸苄酯 、 丁二酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 16.0h， 以97%的产率得到bis[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] butanedioate
  参考文献：
  名称：

  Symmetrical biodegradable crosslinkers for use in polymeric devices

  摘要：

  There is a need for biodegradable hydrogels that deteriorate at defined rates under physiological conditions for use in engineered tissue constructs and drug delivery. These hydrogels should contain components that are readily synthesized, biocompatible and easily incorporated into hydrogel networks. This need was addressed through a judiciously designed series of crosslinkers composed of symmetrical oligo-glycolate and oligo-lactate esters terminated with vinylic moieties (1). These materials were incorporated into poly(HPMA) networks via free-radical polymerization. This work describes the preparation of symmetrical, lactate and glycolate ester based crosslinking agents and their incorporation into a hydrogel network composed of 2-hydroxypropyl methacrylamide (HPMA). By varying the number of lactic and glycolic acid residues (n = 0, 1, 2) within the crosslinker, the rate of hydrolytic degradation of the gel can be controlled. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.066

文献信息

• Degradable cross-linking agents and cross-linked network polymers formed therewith
  申请人：——

  公开号：US20030078339A1

  公开（公告）日：2003-04-24

  Degradable cross-linkers which are used to form polymer networks which degrade under aqueous conditions are described. These cross-linkers comprise a central polyacid, monomeric or oligomeric degradable regions and an optional water soluble regions. These monomers are preferably polymerized using free radical or condensation polymerization. Degradation occurs at the ester linkages after cross-linking polymer filaments, and results in soluble polymer filaments which may be cleared from the body. Preferred applications of these materials include, for example, controlled release of drugs and cosmetics, tissue engineering, wound healing, hazardous waste remediation, metal chelation, swellable devices for absorbing liquids and the prevention of surgical adhesions.

  可降解交联剂可用于形成在水性条件下降解的聚合物网络。这些交联剂由中心聚酸、单体或低聚物可降解区以及任选的水溶性区组成。这些单体最好采用自由基聚合或缩合聚合。在交联聚合物丝后，酯连接处会发生降解，从而产生可从体内清除的可溶性聚合物丝。这些材料的首选应用包括药物和化妆品的控释、组织工程、伤口愈合、有害废物修复、金属螯合、吸收液体的可膨胀装置以及防止手术粘连等。
• DEGRADABLE CROSS-LINKING AGENTS AND CROSS-LINKED NETWORK POLYMERS FORMED THEREWITH
  申请人：Access Pharmaceuticals, Inc.

  公开号：EP1263849A1

  公开（公告）日：2002-12-11
• US6521431B1
  申请人：——

  公开号：US6521431B1

  公开（公告）日：2003-02-18
• [EN] DEGRADABLE CROSS-LINKING AGENTS AND CROSS-LINKED NETWORK POLYMERS FORMED THEREWITH<br/>[FR] AGENTS DE RETICULATION BIODEGRADABLES ET FORMATION DE POLYMERES RETICULES
  申请人：ACCESS PHARMA INC

  公开号：WO2000078846A1

  公开（公告）日：2000-12-28

  Degradable cross-linkers which are used to form polymer networks which degrade under aqueous conditions are described. These cross-linkers comprise a monodispersed central polyacid, monodispersed monomeric or monodispersed oligomeric degradable regions and an optional water soluble regions. These monomers are preferably polymerized using free radical or condensation polymerization. Degradation occurs at degradable regions such as ester linkages after cross-linking polymer filaments, and results in soluble polymer filaments which may be cleared from the body. Preferred applications of these materials include, for example, controlled release of drugs and cosmetics, tissue engineering, wound healing, hazardous waste remediation, metal chelation, swellable devices for absorbing liquids and the prevention of surgical adhesions.
• Symmetrical biodegradable crosslinkers for use in polymeric devices
  作者：Allen A. Thomas、In Tae Kim、Patrick F. Kiser

  DOI：10.1016/j.tetlet.2005.10.066

  日期：2005.12

  There is a need for biodegradable hydrogels that deteriorate at defined rates under physiological conditions for use in engineered tissue constructs and drug delivery. These hydrogels should contain components that are readily synthesized, biocompatible and easily incorporated into hydrogel networks. This need was addressed through a judiciously designed series of crosslinkers composed of symmetrical oligo-glycolate and oligo-lactate esters terminated with vinylic moieties (1). These materials were incorporated into poly(HPMA) networks via free-radical polymerization. This work describes the preparation of symmetrical, lactate and glycolate ester based crosslinking agents and their incorporation into a hydrogel network composed of 2-hydroxypropyl methacrylamide (HPMA). By varying the number of lactic and glycolic acid residues (n = 0, 1, 2) within the crosslinker, the rate of hydrolytic degradation of the gel can be controlled. (c) 2005 Elsevier Ltd. All rights reserved.