4-hept-1-ynyl-benzaldehyde | 121866-31-7

• 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-hept-1-ynyl-benzaldehyde
• 英文别名: 4-hept-1-ynylbenzaldehyde
• CAS: 121866-31-7
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: UOVJILAPVLPLBT-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±25.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-hept-1-ynyl-benzaldehyde 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-正庚基苯甲醛
  参考文献：
  名称：

  Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

  摘要：

  A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 +/- 0.2 mu M. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R-2) = 0.92, Q(2) = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.083
• 作为产物：
  描述：

  1-庚炔 、 对溴苯甲醛 在 copper(I) bromide 、 四(三苯基膦)钯 、 三乙胺 作用下， 生成 4-hept-1-ynyl-benzaldehyde
  参考文献：
  名称：

  Rates and regioselectivities of the palladium-catalyzed ethynylation of substituted bromo- and dibromobenzenes

  摘要：

  DOI：

  10.1021/jo00279a040

文献信息

• [EN] A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES<br/>[FR] PROCÉDÉ POUR LE COUPLAGE CATALYSÉ PAR LE PALLADIUM D'ALCYNES TERMINALES AVEC DES TOSYLATES D'ARYLE
  申请人：SANOFI AVENTIS

  公开号：WO2009003589A1

  公开（公告）日：2009-01-08

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula (I) useful for the production of intermediates in the preparation for pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.

  本发明涉及一种用于选择性合成公式(I)化合物的过程，其中R1；R2；R3；R4；R5；J和W具有声明中指示的含义。本发明提供了一种高效和通用的钯催化偶联过程，可将芳基磺酸酯与末端炔烃偶联，形成一系列取代的、多功能的芳基-1-炔烃，其化学式为(I)，用于制备制药品、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀灭剂、寄生虫杀灭剂、杀虫剂、螨虫剂和节肢动物杀灭剂的中间体。
• A General Palladium-Catalyzed Sonogashira Coupling of Aryl and Heteroaryl Tosylates
  作者：Omar R'kyek、Nis Halland、Andreas Lindenschmidt、Jorge Alonso、Peter Lindemann、Matthias Urmann、Marc Nazaré

  DOI：10.1002/chem.201001524

  日期：2010.9.3

  Coupled up: A new general palladium‐catalyzed procedure for the cross‐coupling of aryl and heteroaryl tosylates is described. This highly versatile and efficient process can be used for the synthesis of a wide variety of functionalized alkynes (see scheme).

  耦合：描述了一种新的通用钯催化的芳基和杂芳基甲苯磺酸盐的交叉偶联方法。这种高度通用和高效的方法可用于合成多种功能化的炔烃（请参见方案）。
• Regiochemical Aspects of the Platinum Oxide Catalyzed Hydrosilylation of Alkynes
  作者：Mouâd Alami、Abdallah Hamze、Olivier Provot、Jean-Daniel Brion

  DOI：10.1055/s-2007-983742

  日期：2007.7

  The platinum-catalyzed hydrosilylation of unsymmetrical substituted arylalkynes with various hydrosilanes was investigated and the reaction selectivity of various para-substituted substrates was compared with that of their corresponding ortho-substituted derivatives. We showed that heterogeneous platinum oxide is a very efficient catalyst for such hydrosilylations and that H-Si bond addition proceeds in a stereoselective cis-fashion. The regioselectivity was found to be under the control of the ortho-substituent rather than due to the nature of the platinum catalyst. Aryl­alkynes with an ortho-substituent provided predominantly to exclusively α-selectivity, regardless of the electronic nature of the substituent. The precise contributions of steric, electronic, and coordinative factors controlling the regioselectivity of the H-Si bond addition are discussed.

  对不对称取代的芳基炔与各种氢硅烷的铂催化氢硅化反应进行了研究，并比较了不同对位取代底物的反应选择性与其相应的邻位取代衍生物的反应选择性。我们展示了异相铂氧化物是一种高效的催化剂用于此类氢硅化反应，且H-Si键的加成以立体选择性的顺式方式进行。区域选择性被发现是由邻位取代基控制，而不是由铂催化剂的性质决定。带有邻位取代基的芳基炔提供了主要到完全的α-选择性，无论取代基的电子性质如何。我们还讨论了影响H-Si键加成的区域选择性的立体、电子和配位因素的精确贡献。
• Process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates
  申请人：RKYEK Omar

  公开号：US20100261910A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula I.

  本发明涉及一种合成式(I)化合物的区域选择性合成方法，其中R1、R2、R3、R4、R5、J和W的含义如权利要求所示。本发明提供了一种高效、通用的钯催化偶联方法，用于将芳基磺酸酯与末端炔烃耦合成式I的多取代多功能芳基-1-炔烃。
• Platinum Oxide Catalyzed Hydrosilylation of Unsymmetrical Internal Aryl Alkynes under Ortho-Substituent Regiocontrol
  作者：Abdallah Hamze、Olivier Provot、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1021/ol052245s

  日期：2005.12.1

  [GRAPHICS]PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylallcynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the a-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.