tert-butyl (2-(2-iodophenoxy)ethyl)carbamate | 1056015-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (2-(2-iodophenoxy)ethyl)carbamate
• 英文别名: tert-butyl N-[2-(2-iodophenoxy)ethyl]carbamate
• CAS: 1056015-76-9
• 化学式: C₁₃H₁₈INO₃
• 分子量: 363.195
• InChiKey: JGTVXVURVGEFEM-UHFFFAOYSA-N

物化性质

• 沸点：
  426.0±30.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(2-iodophenoxy)ethyl)carbamate 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 六氟合硅酸 、 二异丙胺 作用下， 以 水 为溶剂， 反应 39.5h， 生成 tert-butyl (2-(2-((4-((3-(2-aminoethoxy)phenyl)ethynyl)-3-(2-((tert-butoxycarbonyl)amino)ethoxy)-phenyl)ethynyl)phenoxy)ethyl)carbamate
  参考文献：
  名称：

  Chemically Fueled Communication Along a Scaffolded Nanoscale Array of Squaramides

  摘要：

  摘要在几个纳米的范围内实现构象变化是异位调节蛋白功能的核心。人工复制这种机制将提供重要的通信工具，但需要纳米级的分子能在确定的形状之间可逆地切换，以响应信号分子。在这项研究中，1.8 纳米长的硬棒寡（苯乙炔）是可切换的多夸酰胺氢键中继的支架。相对于支架，每个中继体可以采用平行或反平行取向；首选取向由一端的导向基决定。一个胺引导基团对质子信号做出反应，酸碱循环产生多个可逆的中继方向变化，距离 1.8 纳米的末端 NH 报告了这些变化。此外，化学燃料也起着耗散信号的作用。随着燃料的消耗，中继器恢复到原来的方向，这说明了失衡分子信号的信息是如何传递到遥远的位置的。

  DOI：

  10.1002/anie.202307841
• 作为产物：
  描述：

  N-(叔丁氧羰基)乙醇胺 在 sodium periodate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2-(2-iodophenoxy)ethyl)carbamate
  参考文献：
  名称：

  铜催化的交叉偶联受Smiles重排的影响：关于使手性氟化1,4-苯并恶嗪衍生物的合成多样化的新篇章†

  摘要：

  研究了由它们的开链前体合成不同的手性氟化Boc- [1,4]苯并恶嗪。NMR光谱和晶体学数据表明，出现了Smiles重排（SR），然后进行了铜催化的偶联。通过仔细的反应优化，详细探讨了Boc保护基，溶剂，碱，催化剂和加合物构象变化的影响。在没有Boc的情况下未获得任何产品，表明其至关重要的作用。最后，提出了一种新的SR铜催化闭环机理。

  DOI：

  10.1039/c5ra18897k

文献信息

• Synthesis of Heteroaryl ortho-Phenoxyethylamines via Suzuki Cross-Coupling: Easy Access to New Potential Scaffolds in Medicinal Chemistry
  作者：Silvia Franchini、Leda Manasieva、Battisti Maria、Adolfo Prandi、Livio Brasili

  DOI：10.1055/s-0035-1560456

  日期：——

  in medicinal chemistry as privileged scaffolds for the design of highly potent and selective ligands. Herein an efficient, fast, and general method for the synthesis of heteroaryl phenoxyethylamines via Suzuki­ cross-coupling is reported. This approach offers the opportunity to obtain a large variety of biaryls incorporating five-membered (thiophene, furan, thiazole, pyrazole, imidazole) or six-membered

  摘要 杂芳基邻苯氧基乙胺已在药物化学中广泛用作特权支架，用于设计高效和选择性的配体。本文报道了通过Suzuki交叉偶联合成杂芳基苯氧基乙胺的有效，快速和通用的方法。这种方法提供了机会，为适当的配体文库获得掺入五元（噻吩，呋喃，噻唑，吡唑，咪唑）或六元（吡啶，嘧啶）杂芳族环的多种联芳基。这里介绍的所有化合物以前从未合成过，并给出了完整的结构表征。 杂芳基邻苯氧基乙胺已在药物化学中广泛用作特权支架，用于设计高效和选择性的配体。本文报道了通过Suzuki交叉偶联合成杂芳基苯氧基乙胺的有效，快速和通用的方法。这种方法提供了机会，为适当的配体文库获得掺入五元（噻吩，呋喃，噻唑，吡唑，咪唑）或六元（吡啶，嘧啶）杂芳族环的多种联芳基。这里介绍的所有化合物以前从未合成过，并给出了完整的结构表征。
• Identification of a Potent and Selective 5-HT_1A Receptor Agonist with <i>In Vitro</i> and <i>In Vivo</i> Antinociceptive Activity
  作者：Pasquale Linciano、Claudia Sorbi、Antonella Comitato、Anna Lesniak、Magdalena Bujalska-Zadrożny、Agata Pawłowska、Anna Bielenica、Jolanta Orzelska-Górka、Ewa Kędzierska、Grażyna Biała、Simone Ronsisvalle、Silvia Limoncella、Livio Casarini、Elena Cichero、Paola Fossa、Grzegorz Satała、Andrzej J. Bojarski、Livio Brasili、Rita Bardoni、Silvia Franchini

  DOI：10.1021/acschemneuro.0c00289

  日期：2020.12.16

  Opioids are the gold standard drugs for the treatment of acute and chronic severe pain, although their serious side effects constitute a big limitation. In the search for new and safer drugs, 5-HT_1AR agonists are emerging as potential candidates in pain relief therapy. In this work, we evaluated the affinity and activity of enantiomers of the two newly synthesized, potent 5-HT_1AR agonists N-[(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-[2-(pyridin-4-yl)phenoxy]ethan-1-ammonium hydrogenoxalate (rac-1) and N-((2,2-diphenyl-1,3-dioxolan-4-yl)methyl)-2-(2-(1-methyl-1H-imidazol-5-yl)phenoxy)ethan-1-ammonium hydrogenoxalate (rac-2) in vitro and in vivo. The role of chirality in the interaction with 5-HT_1AR was evaluated by molecular docking. The activity of the rac-1 was tested in mouse models of acute pain (hot plate) and severe tonic nociceptive stimulation (intraplantar formalin test). Rac-1 was active in the formalin test with a reduction in paw licking in both phases at 10 mg/kg, and its effect was abolished by the selective 5-HT_1AR antagonist, WAY-100635. The eutomer (S)-1, but not the racemate, was active during the hot plate test at 10 and 20 mg/kg, and this effect was abolished by 30 min treatment with WAY-100635 at 30 min. Similarly to 8-OH-DPAT, (S)-1 evoked a slow outward current and depressed spontaneous glutamatergic transmission in superficial dorsal horn neurons, more effectively than rac-1. The eutomer (S)-1 showed promising developability properties, such as high selectivity over 5-HT subtypes, no interaction with the μ receptors, and low hepato- and cardiotoxicity. Therefore, (S)-1 may represent a potential candidate for the treatment of acute and chronic pain without having the adverse effects that are commonly associated with the classic opioid drugs.
• Fluorescence and Hybridization Properties of Peptide Nucleic Acid Containing a Substituted Phenylpyrrolocytosine Designed to Engage Guanine with an Additional H-Bond
  作者：Filip Wojciechowski、Robert H. E. Hudson

  DOI：10.1021/ja804233g

  日期：2008.9.24

  A new pyrrolocytosine derivative has been designed to selectively interact with guanine and has been evaluated in peptide nucleic acid where it imparts increased selective binding affinity for complementary oligonucleotides. The modified nucleobase also possesses an exceptionally high fluorescence quantum yield that is responsive to hybridization.