(2-chlorophenyl)(thiophen-2-yl)methanone | 6933-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-chlorophenyl)(thiophen-2-yl)methanone
• 英文别名: (2-chlorophenyl)-thiophen-2-ylmethanone
• CAS: 6933-31-9
• 化学式: C₁₁H₇ClOS
• 分子量: 222.695
• InChiKey: QMDWNQPWWNZRGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  160 °C(Press: 1.6 Torr)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-chlorophenyl)(thiophen-2-yl)methanone 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到2-chlorophenyl(2-thienyl)methanol
  参考文献：
  名称：

  Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation

  摘要：

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-{alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

  DOI：

  10.1021/jm050273a
• 作为产物：
  描述：

  2-chlorophenyl(2-thienyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2-chlorophenyl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  CuII催化的二芳基和芳基杂芳基酮的不对称硅氢加成反应：在对苯二酚和新贝诺定的对映选择性合成中的应用

  摘要：

  用一定量的钠的叔丁醇和叔丁醇作为添加剂，催化量的一种廉价的和易于手柄铜源的Cu（OAc）2 ⋅ ħ 2O，一种可商购的且稳定的非外消旋二吡啶基膦配体，以及理想的化学计量的氢化物供体聚甲基氢硅氧烷（PMHS），形成了一种通用的原位催化剂体系，用于对映选择性还原广谱的手性二芳基和芳基杂芳基酮空气，产率高，对映选择性好（至96％）。特别地，该方法的实际可行性通过其在光学富集的有效抗组胺药奥芬那君和新贝尼定的不对称合成中的成功应用得到证明。

  DOI：

  10.1002/chem.201200379

文献信息

• One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling
  作者：Hongxiang Wu、Baiping Xu、Yue Li、Fengying Hong、Dezhao Zhu、Junsheng Jian、Xiaoer Pu、Zhuo Zeng

  DOI：10.1021/acs.joc.5b02667

  日期：2016.4.1

  A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min.

  已经开发了钯催化的一锅法合成芳基酮。三嗪酸酯与芳基硼酸偶联时，在1 mol％Pd（PPh 3）2 Cl 2存在下30分钟，以中等至极好的收率（高达95％）提供芳基酮。
• Rhodium-catalyzed Synthesis of 1-Arylisoquinoline Derivatives through Annulative Coupling of 3-Aryl-1,2-benzisoxazoles and Alkynes
  作者：Teppei Noguchi、Yuji Nishii、Masahiro Miura

  DOI：10.1246/cl.170618

  日期：2017.10.5

  annulative coupling of 3-aryl-1,2-benzisoxazoles and alkynes efficiently proceeds in the presence of a Cp*Rh(III) catalyst to produce 2-(1-isoquinolinyl)phenols of interest in medicinal chemistry as well as materials chemistry. The products may also be useful precursors of quinoline-based bidentate ligands.

  在 Cp*Rh(III) 催化剂的存在下，3-芳基-1,2-苯并异恶唑和炔烃的直接环化偶联有效地进行，以生产药物化学和材料化学中感兴趣的 2-(1-异喹啉基) 苯酚。产物也可以是基于喹啉的双齿配体的有用前体。
• Ni and Cu-catalyzed one pot synthesis of unsymmetrical 1,3-di(hetero)aryl-1H-indazoles from hydrazine, o-chloro (hetero)benzophenones, and (hetero)aryl bromides
  作者：Carson Wiethan、Christopher M. Lavoie、Andrey Borzenko、Jillian S. K. Clark、Helio G. Bonacorso、Mark Stradiotto

  DOI：10.1039/c7ob00841d

  日期：——

  cyclization of in situ generated ortho-chlorobenzophenone hydrazone derivatives, to afford 3-(hetero)aryl-1H-indazoles, is documented for the first time. The product 1H-indazoles can be transformed subsequently in a one-pot procedure into 1,3-di(hetero)aryl-1H-indazoles via copper-catalyzed N-arylation with (hetero)aryl bromides.

  首次记载了镍催化的原位生成的邻氯二苯甲酮derivatives衍生物的环化反应，得到3-（杂）芳基-1 H-吲唑。产物1 H-吲唑可随后通过一锅法经铜与（杂）芳基溴的N-芳基化反应转变为1,3-二（杂）芳基-1 H-吲唑。
• TFAA/H₃PO₄-Mediated C-2 Acylation of Thiophene: A Direct Synthesis of Known and Novel Thiophene Derivatives of Pharmacological Interest
  作者：P. Bindu、Shravan Reddy Naini、K. Shanmukha Rao、P. K. Dubey、Sarbani Pal

  DOI：10.1002/jhet.1106

  日期：2014.5

  aliphatic and aromatic carboxylic acids were reacted with thiophene in the presence of trifluoroacetic anhydride and H3PO4 to give a variety of acylated thiophenes in good to excellent yields. The methodology was used to prepare known nonsteroidal anti‐inflammatory drug‐based novel compounds of potential pharmacological significances. Molecular modeling studies were carried out by using nonsteroidal

  在三氟乙酸酐和H 3 PO 4的存在下，许多脂肪族和芳香族羧酸与噻吩反应，以良好或优异的收率得到各种酰化的噻吩。该方法用于制备具有潜在药理学意义的已知的基于非甾体抗炎药的新型化合物。分子建模研究是通过使用基于非甾体抗炎药的噻吩衍生物评估其环氧化酶在计算机上的抑制潜力而进行的。在对接研究和随后的体外测定的基础上，基于消炎痛的噻吩衍生物被鉴定为具有平衡选择性的新型环氧合酶2抑制剂。
• In Situ Generation of Palladium Nanoparticles: Ligand-Free Palladium Catalyzed Pivalic Acid Assisted Carbonylative Suzuki Reactions at Ambient Conditions
  作者：Qing Zhou、Shaohua Wei、Wei Han

  DOI：10.1021/jo402366p

  日期：2014.2.7

  selective carbonylative Suzuki reactions of aryl iodides with arylboronic acids using an in situ generated nanopalladium system furnished products in high yields. The reactions were performed under ambient conditions and in the absence of an added ligand. The key to success is the addition of pivalic acid, which can effectively suppress undesired Suzuki coupling. The synthesis can be easily scaled up, and

  使用原位生成的纳米钯系统，芳基碘化物与芳基硼酸的高度选择性羰基化Suzuki反应可提供高收率的产品。反应在环境条件下和不存在添加的配体的情况下进行。成功的关键是添加新戊酸，它可以有效抑制不希望的Suzuki偶联。合成很容易扩大规模，催化体系最多可重复使用9次。讨论了活性催化物质的性质。