3-(2-chlorophenoxy)-1-propyne | 17061-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-chlorophenoxy)-1-propyne
• 英文别名: 1-chloro-2-(prop-2-yn-1-yloxy)benzene；1-chloro-2-(prop-2-ynyloxy)benzene；1-chloro-2-prop-2-ynoxybenzene
• CAS: 17061-92-6
• 化学式: C₉H₇ClO
• mdl: MFCD13192002
• 分子量: 166.607
• InChiKey: CPJYMVHZHGCWOU-UHFFFAOYSA-N

物化性质

• 沸点：
  74-76 °C(Press: 3 Torr)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-chlorophenoxy)-1-propyne 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 0.5h， 生成 2,6-Bis[3-(2-chlorophenoxy)propyl]-1-methylpyridin-1-ium;trifluoromethanesulfonate
  参考文献：
  名称：

  Strategies To Reduce hERG K⁺Channel Blockade. Exploring Heteroaromaticity and Rigidity in Novel Pyridine Analogues of Dofetilide

  摘要：

  Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG interaction but most importantly may reveal drug design principles to reduce hERG affinity. In the present study, a novel library of neutral and positively charged heteroaromatic derivatives of the class III antiarrhythmic agent dofetilide was synthesized and assessed for hERG affinity in radioligand binding and manual patch clamp assays. Structural modifications of the pyridine moiety, side chain, and peripheral aromatic moieties were evaluated, thereby revealing approaches for reducing hERG binding affinity. In particular, we found that the extra rigidity imposed close to the positively charged pyridine moiety can be very efficient in decreasing hERG affinity.

  DOI：

  10.1021/jm301564f
• 作为产物：
  描述：

  甲磺酸-2-丙炔-1-醇 、 邻氯苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以72%的产率得到3-(2-chlorophenoxy)-1-propyne
  参考文献：
  名称：

  Waste-minimised copper-catalysed azide–alkyne cycloaddition in Polarclean as a reusable and safe reaction medium

  摘要：

  在这里，我们报告了一种通常有用的有机反应的第一个例子，即铜催化的偶氮化物-炔烃环加成反应，在Polarclean/水混合物中作为反应介质进行。

  DOI：

  10.1039/c7gc03022c

文献信息

• Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
  作者：Atulkumar Kamble、Ravindra Kamble、Suneel Dodamani、Sunil Jalalpure、Vijaykumar Rasal、Mahadev Kumbar、Shrinivas Joshi、Sheshagiri Dixit

  DOI：10.1007/s12272-017-0887-0

  日期：2017.4

  In the present paper 5-[4′-(4-[(4-aryloxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles (5a–g) and [2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl-substituted-1-carbodithioates (11h–q) have been designed and synthesized. These compounds were subjected to docking (against AT1 receptor protein enzyme in complex with Lisinopril), in vitro angiotensin converting enzyme inhibition

  在本文中 5-[4'-(4-[(4-芳氧基)甲基]-1H-1,2,3-三唑-1-基}甲基)[1,1'-联苯]-2-基]-1H-四唑 (5a-g) 和 [2'-(1H-四唑-5-基)[1,1'-联苯]-4-基]甲基-取代的-1-碳二硫代酸酯 (11h-q)已经设计和合成。这些化合物经过对接（针对与赖诺普利复合的 AT1 受体蛋白酶）、体外血管紧张素转化酶抑制、抗增殖、抗炎筛选（通过卵白蛋白变性抑制和红细胞膜稳定试验），最后抗- 真菌活性分析。一些化合物已显示出显着的药理特性。
• Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
  作者：Xiang-Ying Tang、Yong-Sheng Zhang、Lv He、Yin Wei、Min Shi

  DOI：10.1039/c4cc08343a

  日期：——

  The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans2and 3-methylene-2,3-dihydroindoles5has been developed via cycloisomerization of N/O-tethered aryltriazoles.

  通过N/O-连接的芳基三唑的环异构化，已经开发出了可控合成3-亚甲基-2,3-二氢苯并呋喃和3-亚甲基-2,3-二氢吲哚。
• [EN] HISTONE DEMENTHYLASE INHIBITORS<br/>[FR] INHIBITEURS D'HISTONE DÉMÉTHYLASE
  申请人：QUANTICEL PHARMACEUTICALS INC

  公开号：WO2014164708A1

  公开（公告）日：2014-10-09

  The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrrolopyridine derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition of histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

  本发明一般涉及治疗癌症和肿瘤性疾病的组合物和方法。本文提供了替代吡咯吡啶衍生物化合物和包含该化合物的药物组合物。所述化合物和组合物对组蛋白去甲基化酶的抑制具有用处。此外，所述化合物和组合物对癌症的治疗具有用处，如前列腺癌、乳腺癌、膀胱癌、肺癌和/或黑色素瘤等。
• Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloaddition
  作者：Dace Rasina、Aurora Lombi、Stefano Santoro、Francesco Ferlin、Luigi Vaccaro

  DOI：10.1039/c6gc01941b

  日期：——

  Herein, we report the first application of the furfuryl alcohol/water azeotrope as a sustainable and easily recoverable reaction medium in organic chemistry. The applicability of this novel medium was tested...

  在此，我们报道了糠醇/水共沸物在有机化学中作为可持续且易于回收的反应介质的首次应用。测试了这种新型培养基的适用性...
• Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins
  作者：Anu Arya、Vinod Kumar、Divya Mathur、Sukhdev Singh、Raju Brahma、Rajpal Singh、Seema Singh、G. L. Sharma、Virinder S. Parmar、Ashok K. Prasad

  DOI：10.1002/jhet.1917

  日期：2015.1

  A series of 50 novel 7‐[2‐hydroxy‐3‐(1,2,3‐triazol‐1‐yl)propyloxy]‐3‐alkyl‐4‐methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)‐catalyzed 1,3‐dipolar cycloaddition reaction “click chemistry” of 7‐(3‐azido‐2‐hydroxypropyloxy)‐3‐alkyl‐4‐methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7‐(3‐azido‐2‐hydroxypropyloxy)‐

  已设计并合成了一系列50种新颖的7- [2-羟基-3-（1,2,3-三唑-1-基）丙氧基] -3-烷基-4-甲基香豆素，并通过Cu（ I）催化7-（3-叠氮基-2-羟基丙氧基）-3-烷基-4-甲基香豆素与各种乙炔衍生物的1,3-偶极环加成反应“点击化学”。反过来，前体化合物，即7-（3-叠氮基-2-羟丙基氧基）-3-烷基-4-甲基香豆素，是通过环氧氯丙烷与7-羟基-3-烷基-4-甲基香豆素缩合而合成的。生成的7-环氧甲氧基-3-烷基-4-甲基香豆素与叠氮化钠中的环氧化物开环。所有合成的化合物均根据其光谱数据分析（IR，1 H-NMR，13 C-NMR光谱和HRMS）进行了明确鉴定。

表征谱图