4-(allyloxycarbonylmethoxy)benzyl 4-nitrophenyl carbonate | 192064-31-6

• 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: 4-(allyloxycarbonylmethoxy)benzyl 4-nitrophenyl carbonate
• 英文别名: 4-nitrophenyl-4'-hydroxymethylphenyl-1'-oxyallylacetate carbonate；4'-nitrophenyl-4-(hydroxymethylphenoxyallylacetate)carbonate；Prop-2-enyl 2-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenoxy]acetate
• CAS: 192064-31-6
• 化学式: C₁₉H₁₇NO₈
• 分子量: 387.346
• InChiKey: ZFQDXQCMEHABPE-UHFFFAOYSA-N

物化性质

• 沸点：
  546.6±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(allyloxycarbonylmethoxy)benzyl 4-nitrophenyl carbonate 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 硫代水杨酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [4-({(4-{tert-Butoxycarbonyl-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-amino}-butyl)-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamoyloxy}-methyl)-phenoxy]-acetic acid
  参考文献：
  名称：

  Optimising inhibitors of Trypanothione reductase using solid-phase chemistry

  摘要：

  A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K-i of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00471-6
• 作为产物：
  描述：

  氯乙酸丙烯酯 在 吡啶 、 sodium cyanoborohydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 4-(allyloxycarbonylmethoxy)benzyl 4-nitrophenyl carbonate
  参考文献：
  名称：

  Optimising inhibitors of Trypanothione reductase using solid-phase chemistry

  摘要：

  A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K-i of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00471-6

文献信息

• Solid-Phase Synthesis of 89 Polyamine-Based Cationic Lipids for DNA Delivery to Mammalian Cells
  作者：Boon-ek Yingyongnarongkul、Mark Howarth、Tim Elliott、Mark Bradley

  DOI：10.1002/chem.200305232

  日期：2004.1.23

  gene delivery systems to overcome extracellular and intracellular barriers is a critical issue for future clinical applications of gene therapy. In recent years much effort has been focused on the development of a variety of DNA carriers, and cationic liposomes have become the most common non-viral gene delivery system. Solid-phase synthesis was used to produce three libraries of polyamine-based cationic

  非病毒基因传递系统克服细胞外和细胞内壁垒的能力是基因治疗未来临床应用的关键问题。近年来，许多努力集中在各种DNA载体的开发上，阳离子脂质体已成为最常见的非病毒基因递送系统。固相合成用于生产三个具有多种疏水性尾巴的多胺基阳离子脂质文库。这些被表征，并且当配制成阳离子脂质体时，确定这些化合物的DNA结合和转染能力的结构-活性关系。两种阳离子脂质产生了人类细胞的高效转染。令人惊讶的是，这两种化合物均来自该文库，具有两个头基和一个脂族尾基，被认为是去污剂样的化合物类别，对转染的研究很少。这些阳离子脂质是用于基因递送的有前途的试剂，并说明了用于脂质复合物发现的固相合成方法的潜力。
• A linker for amidines in solid phase synthesis
  作者：Patrick Roussel、Mark Bradley、Ian Matthews、Peter Kane

  DOI：10.1016/s0040-4039(97)01013-7

  日期：1997.7

  A range of linkers for the important amidine pharmacophore, cleavable using acid or light have been developed for use in library synthesis. The utility of these linkers is demonstrated by the solid phase synthesis of the Novartis (ex-Ciba) phase II compound CGS-25019C.

  已经开发了重要的am药药基团的一系列连接基，可使用酸或光将其裂解以用于文库合成。诺华（Ciba前）II期化合物CGS-25019C的固相合成证明了这些接头的效用。
• Solid-phase synthesis of a lysine-capped bis-dendron with remarkable DNA delivery abilities
  作者：Siew-Eng How、Asier Unciti-Broceta、Rosario M. Sánchez-Martín、Mark Bradley

  DOI：10.1039/b804771e

  日期：——

  Solid-phase synthesis of a generation 3.0 polyamidourea 1→3 C-branched bis-dendron followed by capping of the peripheral amino groups with L-lysine gave an efficient transfection reagent.

  固相合成第 3.0 代聚氨基脲 1→3 C 支链双树枝状化合物，然后用 L-赖氨酸封盖外围氨基，就得到了一种高效的转染试剂。
• Inhibition of the tissue factor/factor VIIa complex — Lead optimisation using combinatorial chemistry
  作者：Patrick Roussel、Mark Bradley、Peter Kane、Christine Bailey、Ruth Arnold、Andrew Cross

  DOI：10.1016/s0040-4020(99)00266-5

  日期：1999.5

  Following a high throughput screen (HTS) for the inhibition of the tissue factor/factor VIIa complex and the identification of a number of original hits a lead optimisation programme was initiated to improve their potency. This necessitated the development of an amidine based linker which allowed the generation of a library of amidinonaphthols prepared both by multiple parallel synthesis (MPS) and split and mix methods. The most active compound had an IC50 of 4 mu M some 10x more potent than the original lead compound, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Internal resin capture — A self purification method for the synthesis of C-terminally modified peptides
  作者：Michael Davies、Mark Bradley

  DOI：10.1016/s0040-4020(99)00146-5

  日期：1999.4

  A synthetic strategy which allows for the general modification of peptides at the C-terminus has long been the goal of the synthetic chemist. We report here the full synthetic details of our inversion and modification methodology demonstrating the method with the synthesis of peptide amides, alcohols, nitriles and a range of other modified peptides. (C) 1999 Elsevier Science Ltd. All rights reserved.