4-hept-1-ynyl-benzoic acid methyl ester | 121866-32-8

• 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-benzoic acid methyl ester
• 英文别名: Methyl 4-(hept-1-yn-1-yl)benzoate；methyl 4-hept-1-ynylbenzoate
• CAS: 121866-32-8
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: PVWAEUHPJKXLBY-UHFFFAOYSA-N

物化性质

• 沸点：
  335.6±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘苯甲酸甲酯 、 dimethylhept-1-ynylaluminum 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 作用下， 以 乙二醇二甲醚 、 正庚烷 为溶剂， 反应 4.0h， 以90%的产率得到4-hept-1-ynyl-benzoic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Aryl Electrophiles with Dimethylalkynylaluminum Reagents

  摘要：

  Alkynyldimethylaluminum reagents are easily available from terminal akynes and trimethylaluminum via a triethylamine-catalyzed metalation. These compounds can react with various aromatic and heterocyclic halides in the presence of palladium in a fast and efficient way. This catalyzed cross-coupling reaction provides a simple entry to numerous internal alkynes, using a readily available, inexpensive, and nontoxic metalating agent.

  DOI：

  10.1021/ol048741i

文献信息

• 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。
• Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides
  作者：Jeongju Moon、Mihee Jang、Sunwoo Lee

  DOI：10.1021/jo802290r

  日期：2009.2.6

  2-Octynoic acid and phenylpropiolic acid were employed for the palladium-catalyzed decarboxylative coupling reaction and with a variety of aryl halides. The former needed 1,4-bis(diphenylphosphino)butane (dppb) as a ligand and the latter tri-tert-butylphosphine (PtBu3), and both required 2 equiv of tetra-n-butylammonium fluoride (TBAF) for full conversion. These reactions showed high reactivities and

  2-辛酸和苯丙酸用于钯催化的脱羧偶联反应以及各种芳基卤化物。前者需要1,4-双（二苯基膦基）丁烷（DPPB）作为配体，而后者三-叔丁基膦（P吨卜3），并且两个需要2当量的四- ñ全丁基氟化铵（TBAF）转换。这些反应显示出高反应性和对官能团如乙烯基，酯，醚，酮和胺的耐受性。
• Palladium(0)-Catalyzed Cross-Coupling of Potassium (<i>Z</i>)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (<i>Z</i>)-Chloroolefins and Trisubstituted Alkenes
  作者：Xavier Guinchard、Xavier Bugaut、Cyril Cook、Emmanuel Roulland

  DOI：10.1002/chem.200900425

  日期：2009.6.2

  Original and ambivalent: We describe the preparation of a series of new potassium trifluoroborates 1, and the study of their behaviour in a Pd0‐catalyzed cross‐coupling reaction. We found that compounds 1 are endowed with original properties as they behave as nucleophilic cross‐coupling partners chemoselectively, but also as ambivalent synthons. The usefulness of this methodology has been successfully

  原始的和矛盾的：我们描述了一系列新的三氟硼酸钾1的制备，以及它们在Pd 0催化的交叉偶联反应中的行为研究。我们发现化合物1具有独特的化学性质，因为它们不仅具有化学选择性的亲核交叉偶联伙伴，而且具有矛盾的合成子。N-酰基亚精胺的首次全合成成功地说明了该方法的有效性。
• Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates
  作者：Pui Ying Choy、Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201001269

  日期：2010.9.3

  Up to speed: The first general and mild protocol for the Sonogashira coupling of aryl mesylates is presented (see scheme). The coupling intermediate also provides facile access to 2‐substituted isoquinolines.

  加快速度：提出了甲磺酸甲磺酸酯的Sonogashira偶联的第一个一般性和温和的方案（请参阅方案）。偶联中间体还提供了2取代异喹啉的便捷通道。
• Rates and regioselectivities of the palladium-catalyzed ethynylation of substituted bromo- and dibromobenzenes
  作者：Rina Singh、George Just

  DOI：10.1021/jo00279a040

  日期：1989.9