benzyl 4-amino-3-iodobenzoate | 1325676-49-0

• 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: benzyl 4-amino-3-iodobenzoate
• CAS: 1325676-49-0
• 化学式: C₁₄H₁₂INO₂
• 分子量: 353.159
• InChiKey: ZSTBBHYBVHPYRY-UHFFFAOYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  474.9±40.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-amino-3-iodobenzoate 在 三乙烯二胺 、 palladium diacetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.75h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of bidentate ligands designed to interact with PDZ domains

  摘要：

  We designed bidentate ligands to target PDZ domains through two binding sites: site S0, delimited by the GLGF loop, and site S1, a zone situated around loop beta(B)/beta(C). A molecular docking study allowed us to design a generic S0 binder, to which was attached a variable size linker, itself linked to an amino acid aimed to interact with the S1 site of PDZ domains. A series of 15 novel bidentate ligands was prepared in 6-11 steps in good overall yield (24-43%). Some of these ligands showed an inhibitory activity against serotonin 5-HT2A receptor/PSD-95 interaction. This was assessed by pull-down assay using a synthetic decapeptide corresponding to the C-terminal residues of the receptor as a bait. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.036
• 作为产物：
  描述：

  苯佐卡因 在 4-二甲氨基吡啶 、 碘 、 silver sulfate 、 三乙胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 benzyl 4-amino-3-iodobenzoate
  参考文献：
  名称：

  Synthesis and evaluation of bidentate ligands designed to interact with PDZ domains

  摘要：

  We designed bidentate ligands to target PDZ domains through two binding sites: site S0, delimited by the GLGF loop, and site S1, a zone situated around loop beta(B)/beta(C). A molecular docking study allowed us to design a generic S0 binder, to which was attached a variable size linker, itself linked to an amino acid aimed to interact with the S1 site of PDZ domains. A series of 15 novel bidentate ligands was prepared in 6-11 steps in good overall yield (24-43%). Some of these ligands showed an inhibitory activity against serotonin 5-HT2A receptor/PSD-95 interaction. This was assessed by pull-down assay using a synthetic decapeptide corresponding to the C-terminal residues of the receptor as a bait. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.036

文献信息

• Cyclic Diaryl λ³-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols <i>via</i> Aryne Intermediates
  作者：Matteo Lanzi、Torben Rogge、Tan Sang Truong、K. N. Houk、Joanna Wencel-Delord

  DOI：10.1021/jacs.2c10090

  日期：2023.1.11

  metal-free, and mild C–C and C–O couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these transformations is further demonstrated via the post-functionalization of C–C and C–O coupling products obtained from reactions of chloranes with

  高价氯烷是一类稀有且未被充分探索的试剂。它们独特的电子特性赋予了与普通碘化物和新出现的溴化物互补的反应性。这里报道了高度化学和区域选择性、无金属和温和的 C-C 和 C-O 偶联。实验和计算机制研究阐明了这些系统前所未有的反应性和选择性以及芳炔中间体的中介作用。通过在不同条件下氯烷与酚类反应获得的 C-C 和 C-O偶联产物的后官能化，进一步证明了这些转化的合成潜力。