methyl 7-phenylhept-6-ynoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 7-phenylhept-6-ynoate
• 英文别名: methyl 7-phenyl-6-heptynate
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: XAVUSXFQUKSIMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  methyl 7-phenylhept-6-ynoate 、 频那醇硼烷 在 C₄₁H₃₆Cl₂CoP₂ 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以78 %的产率得到methyl (Z)-7-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-enoate
  参考文献：
  名称：

  高区域选择性钴催化内炔烃的硼氢化

  摘要：

  利用新开发的环丙烷基二膦配体修饰的钴催化剂，实现了不对称内炔烃的高选择性硼氢化反应，该反应具有独特的区域选择性、广泛的底物范围和良好的官能团相容性。目前的协议能够合成新的烯基硼酸盐，并提高了生物活性化合物的合成效率。

  DOI：

  10.1002/anie.202208473
• 作为产物：
  描述：

  6-庚炔酸 在 cesium hydroxide 、 PS-PEG resin supported palladium 作用下， 以 水 为溶剂， 反应 12.0h， 生成 methyl 7-phenylhept-6-ynoate
  参考文献：
  名称：

  The Sonogashira Reaction in Water via an Amphiphilic Resin-supported Palladium-Phosphine Complex under Copper-free Conditions

  摘要：

  The Sonogashira reaction of aryl halides with terminal alkynes was catalyzed by an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported palladium-phosphine complex in water to give the corresponding aryl-substituted alkynes in high yields under copper-free conditions. Reaction of o-iodophenol with terminal alkynes under Sonogashira conditions gave benzofuran derivatives in one step.

  DOI：

  10.3987/com-02-s21

文献信息

• Ru(II)‐Catalyzed Regioselective Hydroarylative Coupling of Indolines with Internal Alkynes by C−H Activation
  作者：Raziullah、Mohit Kumar、Afsar Ali Khan、Himangsu Sekhar Dutta、Ashfaq Ahmad、Jayanti Vaishnav、Ruchir Kant、Ravi Sankar Ampapathi、Dipankar Koley

  DOI：10.1002/ejoc.202100085

  日期：2021.4.15

  A hydroarylative coupling of internal alkynes with indolines and tetrahydroquinolines has been developed using the bench‐stable and inexpensive ruthenium (II) catalyst. The applicability of this methodology has been demonstrated by the late stage functionalization of natural products, biologically active molecules, and APIs.

  使用稳定且廉价的钌（II）催化剂开发了内部炔烃与二氢吲哚和四氢喹啉的加氢芳基化偶联剂。天然产物，生物活性分子和API的后期功能化已证明了该方法的适用性。
• Indirect Electroreductive Sequential Radical Reaction Catalyzed by a Ni(II) Complex. One-Step Preparation of Functionalized (Methylene)cyclopentanes.
  作者：Shigeko OZAKI、Shizue MITOH、Hidenobu OHMORI

  DOI：10.1248/cpb.43.1435

  日期：——

  Substituted (methylene)cyclopentanes were prepared by one-step reaction at room temperature from butynyl iodides and activated olefins by sequencing of free radical addition and cyclization reactions. The reactions, which were conducted by indirect electroreduction catalyzed by a nickel(II) complex, proceeded with modest selectivity for formation of the Z(methylene)cyclopentanes.

  通过一步反应，在室温下利用丁炔基碘和活化烯烃，通过自由基加成和环化反应的序列，制备了取代的(methylene)环戊烷。这些反应是在镍(II)配合物催化下进行的间接电还原反应，形成Z(methylene)环戊烷时具有适度的选择性。
• Nickel-Catalyzed Sonogashira Coupling Reactions of Nonactivated Alkyl Chlorides under Mild Conditions
  作者：Qingqing Fan、Hongjian Sun、Shangqing Xie、Yanhong Dong、Xiaoyan Li、Olaf Fuhr、Dieter Fenske

  DOI：10.1021/acs.organomet.0c00793

  日期：2021.7.26

  additive complex 1 could effectively catalyze the C(sp3)–C(sp) coupling of nonactivated alkyl chlorides with alkynes under mild conditions (50 °C) with low catalyst loading (1 mol %). Complex 1 is easy to synthesize and has efficient catalytic activity, especially for alkyl chlorides, under mild conditions.

  分别具有[P,S]和[P,Se]双齿配体的两种氯化镍1和2被合成并用作Sonogashira偶联反应的催化剂。既1和2是用于薗头C（SP高效催化剂3）-C（SP）偶联反应。配合物1比配合物2具有更好的催化活性。在 1 mol % 催化剂负载量1和 CuI/Cs 2 CO 3 的组合中/DMSO 在 25 °C 下用于烷基碘与末端炔烃的偶联反应，以中等至优异的产率获得相应的偶联产物。该催化体系也适用于 40 °C 的烷基溴。必须指出的是，以 NaI 作为添加剂配合物1可以在温和条件 (50 °C) 和低催化剂负载量 (1 mol %) 下有效催化未活化的烷基氯化物与炔烃的 C(sp 3 )–C(sp) 偶联）。配合物1易于合成，在温和条件下具有高效的催化活性，特别是对烷基氯化物。
• Ru-Catalyzed C–H alkenylation on the arene ring of pirfenidone using pyridone as a directing group
  作者：Raziullah、Mohit Kumar、Ashfaq Ahmad、Himangsu Sekhar Dutta、Anushka Rastogi、Manoj Kumar Gangwar、Dipankar Koley

  DOI：10.1039/d2cc00257d

  日期：——

  A method to functionalize the arene ring of pirfenidone has been demonstrated using pyridone as a directing group. Unlike the functionalization of the pyridone nucleus, the method demonstrated here is the alkenylation of the N-aryl ring of pirfenidone with internal alkynes using ruthenium catalyst. High functional group tolerance, simple reaction conditions and site-selective functionalization permit

  已经证明了使用吡啶酮作为导向基团来官能化吡非尼酮芳烃环的方法。与吡啶酮核的功能化不同，这里展示的方法是使用钌催化剂将吡非尼酮的N-芳基环与内部炔烃进行烯基化。高官能团耐受性、简单的反应条件和位点选择性功能化允许以逐步经济的方式合成新的药物类似物。对照实验的数据表明碱辅助内部亲电取代 (BIES) 途径的可能性。
• Relay Catalysis for Selective Aerobic Oxidative Esterification of Primary Alcohols with Methanol
  作者：Yibo Yu、Jie Lin、Anni Qin、Huanan Wang、Jie Wang、Weiyi Wang、Guolin Wu、Qian Zhang、Hui Qian、Shengming Ma

  DOI：10.1021/acs.orglett.4c01059

  日期：2024.4.26

  and ubiquitous in polymers, bioactive compounds, and natural products. Their traditional synthetic approach is the esterification of carboxylic acids or their activated derivatives with alcohols. Herein, a bimetallic relay catalytic protocol was developed for the aerobic esterification of one alcohol in the presence of a slowly oxidizing alcohol, which has been identified as methanol. A concise synthesis

  酯是大宗化学品和精细化学品，普遍存在于聚合物、生物活性化合物和天然产品中。他们的传统合成方法是羧酸或其活化衍生物与醇的酯化。在此，开发了一种双金属中继催化方案，用于在缓慢氧化的醇（已被鉴定为甲醇）存在下对一种醇进行有氧酯化。进行了邻苯酸的简明合成以证明该反应的实用性和潜力。