ethyl 4-(hept-1-ynyl)benzoate | 827028-05-7

• 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: ethyl 4-(hept-1-ynyl)benzoate
• 英文别名: Ethyl 4-(hept-1-YN-1-YL)benzoate；ethyl 4-hept-1-ynylbenzoate
• CAS: 827028-05-7
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: XFOYCVYAAUBOEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-(hept-1-ynyl)benzoate 在 10percent Pd/C manganese oxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-正庚基苯甲醛
  参考文献：
  名称：

  Development of Novel EDG3 Antagonists Using a 3D Database Search and Their Structure−Activity Relationships

  摘要：

  Sphingosine-1-phosphate (SIP) is an intracellular second messenger and an extracellular mediator through endothelial differentiation gene (EDG) receptors, which are a novel class of G-protein-coupled receptors. Although EDG has attracted much attention because of its various roles, no selective agonists or antagonists have yet been developed. This could account for the delay in clarifying the physiological roles of members of the EDG family. Because precise structural information on EDG receptors is not yet available, pharmacophore models were generated based on structural information for SIP using the rational drug design software Catalyst. Novel antagonists, 2-alkylthiazolidine-4-carboxylic acids, were retrieved from a three-dimensional database search using the pharmacophore models, and these showed activity for EDG3. On the basis of their nonphosphoric acid structure, more potent antagonists, 2-(m- or p-heptylphenyl)thiazolidine-4-carboxylic acid, were developed.

  DOI：

  10.1021/jm020080c
• 作为产物：
  描述：

  1-庚炔 、 对碘苯甲酸乙酯 在 palladium on activated charcoal copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以98%的产率得到ethyl 4-(hept-1-ynyl)benzoate
  参考文献：
  名称：

  Sonogashira Cross-Coupling Using Carbon Aerogel Doped with Palladium Nanoparticles; A Recoverable and Reusable Catalyst

  摘要：

  在掺杂金属钯纳米粒子的碳气凝胶存在下，进行了芳基碘与末端炔烃的Sonogashira交叉偶联反应。偶联产物以优异的产率被分离出来，催化体系可以在空气中轻松回收，无需特别预防措施，并可多次重复使用。

  DOI：

  10.1055/s-2007-983888

文献信息

• Palladium-Catalyzed Decarboxylative<i>sp</i>-<i>sp</i>²Cross-Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β-Ynoic Acids using Silver Oxide
  作者：Hyunseok Kim、Phil Ho Lee

  DOI：10.1002/adsc.200900502

  日期：2009.11

  Palladium-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide have been developed. A variety of α,β-ynoic acids were readily decarboxylated in the presence of silver oxide and then, generated in situ, silver acetylides were coupled with electrophiles in the presence of a palladium(0) catalyst under neutral conditions

  已经开发了使用氧化银的芳族卤化物和乙烯基卤化物以及三氟甲磺酸与钯，α-炔酸的钯催化的脱羧sp-sp 2交叉偶联反应。多种α，β炔酸在氧化银的存在下，容易地脱羧，然后，生成的原位，银乙炔化物加上在中性条件下在钯（0）催化剂的存在下亲电子，产生对称或不对称的二芳基乙炔，芳基烷基乙炔和芳基乙烯基乙炔，收率良好至优异。
• Use of functionalized onium salts as a soluble support for organic synthesis
  申请人：Vaultier Michel

  公开号：US20070043234A1

  公开（公告）日：2007-02-22

  The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A 1 + , X 1 − , wherein A 1 + represents a cation and X 1 − represents an anion.

  该发明涉及使用至少一个有机功能官能化的离子盐作为可溶性支持体，在至少一个有机溶剂的存在下，用于在均相相中通过至少一个所述有机功能的转化对分子进行有机合成。该离子盐使合成的分子能够被释放。该离子盐在室温下以液态或固态形式存在，符合以下公式A1+，X1−，其中A1+代表阳离子，X1−代表阴离子。
• 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。
• 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.
• Sonogashira Cross-Coupling Using Carbon Aerogel Doped with Palladium Nanoparticles; A Recoverable and Reusable Catalyst
  作者：Sandro Cacchi、Adelina Vallribera、Roger Soler、Giancarlo Fabrizi、Giovanni Forte、Laura Martín、Sandra Martínez、Elies Molins、Marcial Moreno-Mañas、Francesco Petrucci、Anna Roig、Rosa Sebastián

  DOI：10.1055/s-2007-983888

  日期：2007.10

  The Sonogashira cross coupling of aryl iodides with terminal alkynes has been carried out in the presence of carbon aerogels doped with metallic palladium nanoparticles. Coupling products have been isolated in excellent yields and the catalyst system can be easily recovered in the presence of air without any particular precautions and reused several times.

  在掺杂金属钯纳米粒子的碳气凝胶存在下，进行了芳基碘与末端炔烃的Sonogashira交叉偶联反应。偶联产物以优异的产率被分离出来，催化体系可以在空气中轻松回收，无需特别预防措施，并可多次重复使用。