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4-(4-nitrophenyl)-benzoic acid tert-butyl ester | 914659-71-5

中文名称
——
中文别名
——
英文名称
4-(4-nitrophenyl)-benzoic acid tert-butyl ester
英文别名
tert-butyl 4-(4-nitrophenyl)benzoate
4-(4-nitrophenyl)-benzoic acid tert-butyl ester化学式
CAS
914659-71-5
化学式
C17H17NO4
mdl
——
分子量
299.326
InChiKey
LFOIDKYVFRTDIP-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.2
  • 重原子数:
    22
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.24
  • 拓扑面积:
    72.1
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4-(4-nitrophenyl)-benzoic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下, 以 四氢呋喃 为溶剂, 生成 Tert-butyl 4-(4-aminophenyl)benzoate
    参考文献:
    名称:
    设计和合成非肽Ras CAAX模拟物作为有效的法呢基转移酶抑制剂。
    摘要:
    ras癌基因产物Ras的半胱氨酸法呢基化对于其转化活性是必需的,并且被法呢基转移酶(FTase)催化。Ras羧基末端四肽CAAX(C是半胱氨酸,A是任何脂肪族氨基酸,X是蛋氨酸或丝氨酸)是FTase识别的最小序列。我们在这里报告Ras CAAX非肽模拟物的设计,合成和生物学特性,其中半胱氨酸通过还原的伪肽键与4-氨基-3'-羧基联苯相连。这些非肽模拟物是FTase的有效抑制剂(IC50 = 40 nM,是最有效的抑制剂),对FTase的选择性高于GGTase I(香叶基香叶基转移酶I)。它们不是法呢基化的底物,没有肽特征,也没有可水解键。结构活性研究揭示了芳基环上羧酸位置以及半胱氨酸酰胺键还原的重要性。在4-氨基-3'-羧基联苯的2-位取代可提高抑制能力,而羧酸的去除则会导致抑制活性降低10倍。
    DOI:
    10.1021/jm950414g
  • 作为产物:
    描述:
    4-羧基苯硼酸四(三苯基膦)钯 硫酸 、 sodium carbonate 作用下, 以 乙醇二氯甲烷甲苯 为溶剂, 反应 36.0h, 生成 4-(4-nitrophenyl)-benzoic acid tert-butyl ester
    参考文献:
    名称:
    Abc Amino Acids:  Design, Synthesis, and Properties of New Photoelastic Amino Acids
    摘要:
    Photoisomerizable amino acids provide a direct avenue to the experimental manipulation of bioactive polypeptides, potentially allowing real-time, remote control of biological systems and enabling useful applications in nanobiotechnology. Herein, we report a new class of photoisomerizable amino acids intended to cause pronounced expansion and contraction in the polypeptide backbone, i.e., to be photoelastic. These compounds, termed Abc amino acids, employ a photoisomerizable azobiphenyl chromophore to control the relative disposition of aminomethyl and carboxyl substituents. Molecular modeling of nine Abc isomers led to the identification of one with particularly attractive properties, including the ability to induce contractions up to 13 angstrom in the backbone upon trans -> cis photoisomerization. This isomer, designated mpAbc, has substituents at meta and para positions on the inner (azolinked) and outer rings, respectively. An efficient synthesis of Fmoc-protected mpAbc was executed in which the biaryl components were formed via Suzuki couplings and the azo linkage was formed via amine/nitroso condensation; protected forms of three other Abc isomers were prepared similarly. An undecapeptide incorporating mpAbc was synthesized by conventional solid-phase methods and displayed characteristic azobenzene photochemical behavior with optimal conversion to the cis isomer at 360 nm and a thermal cis -> trans half-life of 100 min at 80 degrees C.
    DOI:
    10.1021/jo060763q
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文献信息

  • Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki–Miyaura coupling without intentionally added base
    作者:Aiichiro Nagaki、Yuya Moriwaki、Jun-ichi Yoshida
    DOI:10.1039/c2cc36197c
    日期:——
    We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding
    我们发现,集成的流动微反应器系统能够使用有机锂化学方法制备带有亲电官能团的硼酸酯,并且可以将其用于Suzuki-Miyaura交叉偶联中而无需故意添加碱。基于此方法,完成了两个带有亲电官能团的芳基卤化物的交叉偶联,以一次获得相应的联芳基化合物。
  • Abc Amino Acids:  Design, Synthesis, and Properties of New Photoelastic Amino Acids
    作者:Robert F. Standaert、Seung Bum Park
    DOI:10.1021/jo060763q
    日期:2006.10.1
    Photoisomerizable amino acids provide a direct avenue to the experimental manipulation of bioactive polypeptides, potentially allowing real-time, remote control of biological systems and enabling useful applications in nanobiotechnology. Herein, we report a new class of photoisomerizable amino acids intended to cause pronounced expansion and contraction in the polypeptide backbone, i.e., to be photoelastic. These compounds, termed Abc amino acids, employ a photoisomerizable azobiphenyl chromophore to control the relative disposition of aminomethyl and carboxyl substituents. Molecular modeling of nine Abc isomers led to the identification of one with particularly attractive properties, including the ability to induce contractions up to 13 angstrom in the backbone upon trans -> cis photoisomerization. This isomer, designated mpAbc, has substituents at meta and para positions on the inner (azolinked) and outer rings, respectively. An efficient synthesis of Fmoc-protected mpAbc was executed in which the biaryl components were formed via Suzuki couplings and the azo linkage was formed via amine/nitroso condensation; protected forms of three other Abc isomers were prepared similarly. An undecapeptide incorporating mpAbc was synthesized by conventional solid-phase methods and displayed characteristic azobenzene photochemical behavior with optimal conversion to the cis isomer at 360 nm and a thermal cis -> trans half-life of 100 min at 80 degrees C.
  • Design and Synthesis of Non-Peptide Ras CAAX Mimetics as Potent Farnesyltransferase Inhibitors
    作者:Yimin Qian、Andreas Vogt、Saïd M. Sebti、Andrew D. Hamilton
    DOI:10.1021/jm950414g
    日期:1996.1.1
    These non-peptide mimetics are potent inhibitors of FTase (IC50 = 40 nM for the most potent inhibitor) and are highly selective for FTase over GGTase I (geranylgeranyltransferase I). They are not substrates for farnesylation, do not have peptidic features, and have no hydrolyzable bonds. Structure-activity studies reveal the importance of the position of the carboxylic acid on the aryl ring as well as
    ras癌基因产物Ras的半胱氨酸法呢基化对于其转化活性是必需的,并且被法呢基转移酶(FTase)催化。Ras羧基末端四肽CAAX(C是半胱氨酸,A是任何脂肪族氨基酸,X是蛋氨酸或丝氨酸)是FTase识别的最小序列。我们在这里报告Ras CAAX非肽模拟物的设计,合成和生物学特性,其中半胱氨酸通过还原的伪肽键与4-氨基-3'-羧基联苯相连。这些非肽模拟物是FTase的有效抑制剂(IC50 = 40 nM,是最有效的抑制剂),对FTase的选择性高于GGTase I(香叶基香叶基转移酶I)。它们不是法呢基化的底物,没有肽特征,也没有可水解键。结构活性研究揭示了芳基环上羧酸位置以及半胱氨酸酰胺键还原的重要性。在4-氨基-3'-羧基联苯的2-位取代可提高抑制能力,而羧酸的去除则会导致抑制活性降低10倍。
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