methyl 4-(pent-4-en-1-ynyl)benzoate | 1415029-98-9

• 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: methyl 4-(pent-4-en-1-ynyl)benzoate
• 英文别名: Methyl 4-pent-4-en-1-ynylbenzoate；methyl 4-pent-4-en-1-ynylbenzoate
• CAS: 1415029-98-9
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: IQNWLPZOPCTVMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2-甲基-3-氧代丁酸叔丁酯 、 methyl 4-(pent-4-en-1-ynyl)benzoate 在 四(三苯基膦)钯 、 C₁₂H₂₈N₂*CHF₃O₃S 、 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 以47 %的产率得到
  参考文献：
  名称：

  通过协同 Pd/手性伯胺催化对 β-酮羰基和醛进行不对称 α-戊二烯基化†

  摘要：

  就原子经济性和步骤经济性而言，用跳过的烯炔或环丙丙基乙炔直接烷基化代表了安装戊二烯基的理想方法。人们经常追求催化不对称形式的开发，并且大部分成功都是通过烯醇化醛实现的。我们在此描述了用于β-酮羰基和醛与跳过的烯炔或环丙丙基乙炔的不对称α-戊二烯基化的协同手性伯胺/Pd催化。该反应构建了无环全碳四元中心，具有高对映选择性、良好的官能团耐受性和可扩展性。

  DOI：

  10.1002/cjoc.202300462
• 作为产物：
  描述：

  乙酸烯丙酯 、 3-(4-(methoxycarbonyl)phenyl)propiolic acid 在 Ni⁽¹⁺⁾*2C₂H₃O₂^(1-)*4H₂O 、 silver(I) acetate 、 1,4-双(二苯基膦)丁烷 、 锌 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以62%的产率得到methyl 4-(pent-4-en-1-ynyl)benzoate
  参考文献：
  名称：

  Nickel-catalyzed decarboxylative coupling reaction of alkynyl carboxylic acids and allyl acetates

  摘要：

  The coupling reaction of aryl alkynyl carboxylic acids and allyl acetates was carried out in the presence of nickel catalyst to produce the allyl alkynes in good yields. The optimized condition is that alkynyl carboxylic acid (1.0 equiv), allyl acetate (2.0 equiv), Ni(OAc)(2)center dot 4H(2)O (10 mol %), AgOAc (10 mol %), and zinc (1.0 equiv) were reacted at 100 degrees C for 0.5 h. In addition, when allyl alcohol was employed instead of allyl acetate, the desired product was obtained in good yield. In addition, when the reaction was carried out in the presence of base such as DBU and Cs2CO3, the allene compounds were formed in good yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.005

文献信息

• Nickel-catalyzed decarboxylative coupling reaction of alkynyl carboxylic acids and allyl acetates
  作者：Juseok Choe、Jiyoung Yang、Kyungho Park、Thiruvengadam Palani、Sunwoo Lee

  DOI：10.1016/j.tetlet.2012.10.005

  日期：2012.12

  The coupling reaction of aryl alkynyl carboxylic acids and allyl acetates was carried out in the presence of nickel catalyst to produce the allyl alkynes in good yields. The optimized condition is that alkynyl carboxylic acid (1.0 equiv), allyl acetate (2.0 equiv), Ni(OAc)(2)center dot 4H(2)O (10 mol %), AgOAc (10 mol %), and zinc (1.0 equiv) were reacted at 100 degrees C for 0.5 h. In addition, when allyl alcohol was employed instead of allyl acetate, the desired product was obtained in good yield. In addition, when the reaction was carried out in the presence of base such as DBU and Cs2CO3, the allene compounds were formed in good yield. (C) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric <scp><i>α</i>‐Pentadienylation</scp> of <scp><i>β</i>‐Ketocarbonyls</scp> and Aldehydes by Synergistic Pd/Chiral Primary Amine Catalysis^†
  作者：Chang You、Sanzhong Luo

  DOI：10.1002/cjoc.202300462

  日期：2023.12.15

  pentadienyl group in terms of atom- and step-economy. The development of catalytic asymmetric versions has been frequently pursued and most of the successes have been achieved with enolizable aldehydes. We herein describe a synergistic chiral primary amine/Pd catalysis for asymmetric α-pentadienylation of β-ketocarbonyls and aldehydes with skipped enynes or cyclopropropylacetylenes. The reaction features the

  就原子经济性和步骤经济性而言，用跳过的烯炔或环丙丙基乙炔直接烷基化代表了安装戊二烯基的理想方法。人们经常追求催化不对称形式的开发，并且大部分成功都是通过烯醇化醛实现的。我们在此描述了用于β-酮羰基和醛与跳过的烯炔或环丙丙基乙炔的不对称α-戊二烯基化的协同手性伯胺/Pd催化。该反应构建了无环全碳四元中心，具有高对映选择性、良好的官能团耐受性和可扩展性。