1-(1-heptynyl)-2-methoxybenzene | 14374-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(1-heptynyl)-2-methoxybenzene
• 英文别名: hept-1-ynyl-2-methoxy-benzene；1-(hept-1-ynyl)-2-methoxybenzene；1-(2-Methoxyphenyl)-1-heptyne；1-hept-1-ynyl-2-methoxybenzene
• CAS: 14374-47-1
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: UQEIIZHFTOXJGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-(1-heptynyl)-2-methoxybenzene 在 盐酸 、 sodium sulfide 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以95%的产率得到1-(2-甲氧基苯基)庚烷-1-酮
  参考文献：
  名称：

  An efficient method for preparation of 3,5-diamino-6-chloropyrazin-2-yl alkyl ketones using a novel acetylene hydration method

  摘要：

  DOI：

  10.1021/jo00266a049
• 作为产物：
  描述：

  1-(2-methoxybenzoyl)hexylidene(triphenyl)phosphorane 生成 1-(1-heptynyl)-2-methoxybenzene
  参考文献：
  名称：

  2-取代的苯并呋喃和苯并噻吩的新合成：简单烷基的新型断裂反应

  摘要：

  （2-甲氧基-和（2-甲基硫代苯甲酰基）亚烷基三苯基苯基膦的快速真空热解导致Ph 3 PO和甲基自由基的损失；所得自由基中间体的环化导致苯并呋喃和苯并噻吩中的2-取代基经历了新的裂解过程。

  DOI：

  10.1016/s0040-4039(00)96366-4

文献信息

• 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。
• Synthesis of 3-selanylbenzo[<i>b</i>]furans promoted by SelectFluor®
  作者：Maurício Carpe Diem Ferreira Xavier、Eduardo Martarelo Andia Sandagorda、José Sebastião Santos Neto、Ricardo Frederico Schumacher、Márcio Santos Silva

  DOI：10.1039/d0ra01907k

  日期：——

  A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor® reagent was developed. This novel methodology provided a greener alternative to generate 3-substituted-benzo[b]furans via a metal-free procedure under mild conditions. The intramolecular cyclization reaction was carried out employing an electrophilic selenium species generated in situ through

  开发了一种简单实用的由 SelectFluor® 试剂介导的3-硒基-苯并[ b ]呋喃合成方案。这种新颖的方法提供了一种在温和条件下通过无金属程序生成 3-取代-苯并[ b ]呋喃的更环保的替代方案。分子内环化反应采用通过 SelectFluor® 和有机二硒化物之间的反应原位产生的亲电硒物质进行。通过异核核磁共振波谱证实了这种亲电硒物质（RSe-F）的形成，并探讨了其反应性。
• Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant
  作者：Gérard Cahiez、Christophe Duplais、Julien Buendia

  DOI：10.1002/anie.200902188

  日期：2009.8.24

  Oxidative heterocoupling between two Grignard reagents RMgX and R′MgX is made possible by manganese catalysis with O2 as an oxidant. This procedure, development of which was based on mechanistic analysis of the corresponding homocoupling reaction, can be steered towards the heterocoupling product at the expense of the homocoupling products by judicious choice of the R and R′ groups (see examples).

  通过以O 2为氧化剂的锰催化，可以实现两种格氏试剂RMgX和R'MgX之间的氧化杂化。该方法的开发是基于对相应的均偶联反应的机理分析，可以通过明智地选择R和R'基团，以牺牲均偶联产物为导向，转向异偶联产物（参见示例）。
• 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。
• Trichloroisocyanuric Acid (TCCA): A Suitable Reagent for the Synthesis of Selanyl‐benzo[ <i>b</i> ]chalcogenophenes
  作者：Gustavo B. Blödorn、Luis Fernando B. Duarte、Juliano A. Roehrs、Márcio S. Silva、José S. S. Neto、Diego Alves

  DOI：10.1002/ejoc.202200775

  日期：2022.10.26

  A new protocol for the synthesis of different 3-organyl-benzo[b]chalcogenophenes was developed through the reaction of diorganyl diselenides with trichloroisocyanuric acid (TCCA) in ethanol. Under the optimized reaction conditions, a range of benzo[b]furans, benzo[b]thiophenes and benzo[b]selenophenes were synthesized in good to excellent yields using mild reaction conditions.

  通过二有机基二硒化物与三氯异氰脲酸 (TCCA) 在乙醇中的反应，开发了一种合成不同 3-有机基苯并[ b ]硫族酚的新方案。在优化的反应条件下，一系列苯并[ b ]呋喃、苯并[ b ]噻吩和苯并[ b ]硒吩类化合物在温和的反应条件下以良好至优异的收率合成。