3-(4-Iodo-phenyl)-propionyl chloride | 49618-02-2

• 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: 3-(4-Iodo-phenyl)-propionyl chloride
• 英文别名: 3-(4-Iodophenyl)propanoyl chloride
• CAS: 49618-02-2
• 化学式: C₉H₈ClIO
• 分子量: 294.519
• InChiKey: BZVVUGKENJGCBW-UHFFFAOYSA-N

物化性质

• 沸点：
  307.9±25.0 °C(Predicted)
• 密度：
  1.739±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-Iodo-phenyl)-propionyl chloride 在 水 、 palladium diacetate 、 碳酸氢钠 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 2-(3-(4-(4-methylphenyl)phenyl)propanamido)benzoic acid
  参考文献：
  名称：

  Affinity and kinetics study of anthranilic acids as HCA2 receptor agonists

  摘要：

  Structure-affinity relationship (SAR) and structure-kinetics relationship (SKR) studies were combined to investigate a series of biphenyl anthranilic acid agonists for the HCA(2) receptor. In total, 27 compounds were synthesized and twelve of them showed higher affinity than nicotinic acid. Two compounds, 6g (IC50 = 75 nM) and 6z (IC50 = 108 nM) showed a longer residence time profile compared to nicotinic acid, exemplified by their kinetic rate index (KRI) values of 1.31 and 1.23, respectively. The SAR study resulted in the novel 2-F, 4-OH derivative (6x) with an IC50 value of 23 nM as the highest affinity HCA(2) agonist of the biphenyl series, although it showed a similar residence time as nicotinic acid. The SAR and SKR data suggest that an early compound selection based on binding kinetics is a promising addition to the lead optimization process. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.018
• 作为产物：
  描述：

  3-(4-碘苯基)丙酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(4-Iodo-phenyl)-propionyl chloride
  参考文献：
  名称：

  铜催化氧化苄基C（sp3）-H环化合成β-内酰胺。

  摘要：

  β-内酰胺由于在天然产物和药物中普遍存在而成为重要的结构基序。我们在此报告了使用t BuOO t Bu合成β-内酰胺的Cu催化的分子内氧化C（sp 3）-H酰胺化反应。该方法基于Kharasch-Sosnovsky酰胺化，不需要C（sp 3）-H键的预功能化或定向基团的安装，从而可以直接合成β-内酰胺。我们的分子内功能化协议可以扩展到各种苄基C（sp 3）-H键，并显示出色的官能团耐受性。

  DOI：

  10.1002/chem.201905777

文献信息

• Mechanism of an Elusive Solvent Effect in Organozinc Reagent Synthesis
  作者：Erin M. Hanada、Kristof Jess、Suzanne A. Blum

  DOI：10.1002/chem.202002214

  日期：2020.11.26

  observation of organozinc intermediates and solvent effects on their build‐up and persistence. When combined with NMR spectroscopy, these imaging data pinpoint the previously elusive mechanistic origin of solvent effects in the synthesis of widely used organozinc reagents. These findings characterize the acceleration of oxidative addition of the starting organoiodide to the surface of zinc metal in DMSO

  在传统的整体分析技术无法直接观察到反应中间体及其在不同溶剂中的不同行为的情况下，通常很难理解溶剂的作用。在此，单颗粒荧光显微镜的灵敏度可以独特地直接观察有机锌中间体以及溶剂对它们的形成和持久性的影响。当与NMR光谱结合使用时，这些成像数据可精确地指出合成广泛使用的有机锌试剂中溶剂作用的先前难以捉摸的机理。这些发现表征了相对于THF，DMSO中的起始有机碘化物向锌金属表面的氧化加成的加速，但是一旦形成，表面中间体在两种溶剂中都表现出相似的持久性。
• Synthesis and in Vitro Evaluation of Iodinated Derivatives of Piperazine as a New Ligand for Sigma Receptor Imaging by Single Photon Emission Computed Tomography
  作者：Masahiko Hirata、Tetsuya Mori、Seigo Soga、Takuya Umeda、Yoshiro Ohmomo

  DOI：10.1248/cpb.54.470

  日期：——

  of radioiodinated analogues of 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine (SA4503) was synthesized and evaluated as a potential brain sigma-1 receptor imaging ligands by single photon emission computed tomography (SPECT). Iodinated analogues of SA4503 (4a-c) were prepared from piperazine in a high yield. The in vitro competition binding studies using [3H] DTG (sigma-1, 2), [3H] (+)-pentazocine

  合成了一系列新的1- [2-（3,4-二甲氧基苯基）乙基] -4-（3-苯基丙基）哌嗪（SA4503）的放射性碘类似物，并被单光子评估为潜在的脑sigma-1受体成像配体发射计算机断层扫描（SPECT）。从哌嗪以高产率制备SA4503的碘化类似物（4a-c）。在[3H] DTG（sigma-1，2），[3H]（+）-喷他佐辛（sigma-1）和[3H] DTG以及carbetapentane（sigma-2）作为sigma的条件下进行体外竞争结合研究受体选择性放射性配体被发现碘化类似物4a-c对sigma受体具有高亲和力（IC50：4a = 7.1、4b = 31.0和4c = 77.3 nM）。特别是，在苯环邻位带有碘的4a的亲和力比SA4503大4.4倍，比氟哌啶醇大3倍。异碘类似物4b与先导化合物SA4503相同。放射性碘化的衍生物[125I] 4a，4b是通过碘脱锡反应以高收率从相
• Reductive Deuteration of Acyl Chlorides for the Synthesis of α,α-Dideuterio Alcohols Using SmI2 and D2O
  作者：Hengzhao Li、Yuxia Hou、Mengqi Peng、Lijun Wang、Junyu Li、Lei Ning、Zemin Lai、Yixuan Li、Jie An

  DOI：10.3390/molecules28010416

  日期：——

  The synthesis of α,α-dideuterio alcohols has been achieved via single electron transfer reductive deuteration of acyl chlorides using SmI2 and D2O. This method is distinguished by its remarkable functional group tolerance and exquisite deuterium incorporation, which has also been applied to the synthesis of valuable deuterated agrochemicals and their building blocks.

  α,α-二氘醇的合成是通过使用 SmI2 和 D2O 对酰氯进行单电子转移还原氘化来实现的。该方法以其卓越的官能团耐受性和精细的氘掺入而著称，也已应用于合成有价值的氘代农用化学品及其结构单元。
• Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists
  作者：Olga Bobileva、Martins Ikaunieks、Gunars Duburs、Ilona Mandrika、Ramona Petrovska、Janis Klovins、Einars Loza

  DOI：10.1016/j.bmc.2017.06.028

  日期：2017.8

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.
• 10.1021/jm950476
  作者：Stark、Purand、Huels、Ligneau、Garbarg、Schwartz、Schunack

  DOI：10.1021/jm950476

  日期：——