4,4'-(1,4-phenylene)bis(but-3-yn-1-ol) | 134519-88-3

• 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: 4,4'-(1,4-phenylene)bis(but-3-yn-1-ol)
• 英文别名: 4,4'-benzene-1,4-diylbisbut-3-yn-1-ol；1,4-bis(4-hydroxy-1-butynyl)benzene；4,4'-(1,4-phenylene)dibut-3-yn-1-ol；4-[4-(4-hydroxybut-1-ynyl)phenyl]but-3-yn-1-ol
• CAS: 134519-88-3
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: UAVWARVMTGUXDP-UHFFFAOYSA-N

物化性质

• 熔点：
  148.4-149.5 °C
• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-(1,4-phenylene)bis(but-3-yn-1-ol) 在 palladium on activated charcoal 氢气 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 4-[4-(4-氧代丁基)苯基]丁醛
  参考文献：
  名称：

  通过sa（II）催化的分子内频哪醇偶联反应合成平面手性对环环烷。

  摘要：

  [反应：见正文]通过sa催化的频哪醇偶联反应合成了一系列[n]对环庚二醇（n = 8-12）以形成ansa桥。通过使用氨基醇助剂及其选择性裂解，通过手性拆分（对于n = 10）或通过结晶诱导的不对称转化（对于n = 11），可以通过几个步骤从二醇中衍生出对映体纯的[n]对环环烷酸酯。

  DOI：

  10.1021/ol0506258
• 作为产物：
  描述：

  1,4-二碘苯 、 1-三甲基甲硅烷基氧基-3-丁炔 在 C₁₆H₂₀Cl₂N₂O₂Pd 、 水 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以90%的产率得到4,4'-(1,4-phenylene)bis(but-3-yn-1-ol)
  参考文献：
  名称：

  Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

  摘要：

  A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross -coupling reactions to proceed at room temperature or 60 degrees C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross -coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.086

文献信息

• Synthesis of Strapped Porphyrins: Toward Isolation of the Chromophore on Semiconductor Surfaces
  作者：Chi-Hang Lee、Elena Galoppini

  DOI：10.1021/jo100434t

  日期：2010.6.4

  Strapped porphyrins, designed to bind planar to semiconductor surfaces, were synthesized as model dyes to study the sensitization processes on metal oxide semiconductor nanoparticles surfaces. The strap was added to limit porphyrin−porphyrin stacking and contacts with the semiconductor, while constraining the anchoring groups’ orientation. Diester ZnPorOMe2 (2b) was made of a Zn(II) 5,10,15,20-tetraphenylporphyrin

  合成设计用于结合平面与半导体表面的带状卟啉作为模型染料，以研究在金属氧化物半导体纳米颗粒表面上的敏化过程。添加表带以限制卟啉-卟啉的堆积和与半导体的接触，同时限制了锚定基团的方向。二酯ZnPorOMe 2（2b）由Zn（II）5,10,15,20-四苯基卟啉（ZnTPP）制成，其中5和15个内消旋苯基由1,4-亚苯基双（丁基-4-氧基）束缚单元（表带）并在间位带有甲基苯甲酸酯（锚定基团）。合成过程涉及有用的中间体二溴化物ZnPorOBr 2（2a）。相应的不含金属的H 2 PorOBr 2的X射线结构表明，在晶体中，条带位于大环上方，并相对于卟啉平面倾斜。表征包括1 H- 1 H COSY，1 H- 13 C HMQC和DEPT。与ZnTPP相比，2b的光谱和电化学性质变化不大，表明该性质不受系链或锚定基团的很大影响。2b的HOMO-LUMO间隙在2.14 V时是ZnTPP衍生物的典型特征。化合物2b与TiO
• Quaternary ammonium compounds having muscle relaxation activity
  申请人：Tobishi Yakuhin Kogyo Kabushiki Kaisha

  公开号：US05093370A1

  公开（公告）日：1992-03-03

  A quaternary ammonium having a muscle relaxation activity compound represented by the formula (I): ##STR1## wherein R.sub.1 represents a methylene, a lower alkylenoxy, a lower alkenylene, a lower alkynylene, --CO--, --COO--, a lower alkylene carbonyloxy, --CH(OR.sub.5)--, a lower alkylenecarbonyl, a hydroxy lower alkylene, --O--, --S--, --SO--, or --SO.sub.2 --; R.sub.2 represents a hydrogen atom, a hydroxy lower alkyl, an aldehyde, a lower alkyl carbonyl, --NO.sub.2, or --NHR.sub.6 ; R.sub.3 represents a hydrogen atom of a group --R.sub.1 --(CH.sub.2).sub.a --[CH(CH.sub.2 A)--CH.sub.2 ].sub.b --A; R.sub.4 represents an anion; R.sub.5 and R.sub.6 represent a hydrogen atom or a acetyl; A represents a quaternary ammonium group; a represents an integer of 1 to 8; b represents 0 or 1; m represents an integer of 1 to 4; and (Z) represents a trivalent benzene ring, a trivalent naphthalene ring, a trivalent diphenyl or a trivalent ethane radical.

  一种具有肌肉松弛活性的四价铵化合物，其化学式为(I)：##STR1## 其中R.sub.1代表亚甲基、较低的烷氧基、较低的烯基、较低的炔基、--CO--、--COO--、较低的烷基羰氧基、--CH(OR.sub.5)--、较低的烯基羰基、羟基较低的烷基、--O--、--S--、--SO--或--SO.sub.2--; R.sub.2代表氢原子、羟基较低烷基、醛、较低烷基羰基、--NO.sub.2或--NHR.sub.6; R.sub.3代表羟基较低烷基的氢原子，一个羟基较低烷基，一个醛基，一个较低烷基羰基，一个--NO.sub.2或--NHR.sub.6; R.sub.3代表一个羟基较低烷基，一个醛基，一个较低烷基羰基，一个--NO.sub.2或--NHR.sub.6; R.sub.4代表一个阴离子; R.sub.5和R.sub.6代表一个氢原子或一个乙酰基; A代表一个四价铵基团; a代表1到8的整数; b代表0或1; m代表1到4的整数; (Z)代表三价苯环、三价萘环、三价二苯基或三价乙烷基。
• Bis-azaaromatic quaternary ammonium salts as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release: An investigation of binding conformation
  作者：Guangrong Zheng、Zhenfa Zhang、Marharyta Pivavarchyk、Agripina G. Deaciuc、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2007.10.052

  日期：2007.12

  A series of conformationally restricted bis-azaaromatic quaternary ammonium salts (3 and 4) have been designed and synthesized in order to investigate the possible binding conformations of N,N'-dodecane-1,12-diyl-bis-3-picolinium dibromide (bPiDDB; 2), a compound which potently inhibits neuronal nicotinic acetylcholine receptors (nAChRs) mediating nicotine-evoked dopamine release. The preliminary structure-activity relationships of these new analogues suggest that bPiDDB binds in an extended conformation at the nAChR binding site, and that flexibility of the linker may be important for its high potency in inhibiting nAChRs mediating nicotine-evoked dopamine release. (c) 2007 Elsevier Ltd. All rights reserved.
• New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation
  作者：Sergio A. Caldarelli、Siham El Fangour、Sharon Wein、Christophe Tran van Ba、Christian Périgaud、Alain Pellet、Henri J. Vial、Suzanne Peyrottes

  DOI：10.1021/jm3014585

  日期：2013.1.24

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).
• US5093370A
  申请人：——

  公开号：US5093370A

  公开（公告）日：1992-03-03