4-methylbenzyl but-3-enoate | 1416170-17-6

• 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-methylbenzyl but-3-enoate
• 英文别名: 4-methylbenzyl 3-butenoate；(4-Methylphenyl)methyl but-3-enoate
• CAS: 1416170-17-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: VKPOHIZKGHNUEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methylbenzyl but-3-enoate 在 basic alumina 作用下， 以 乙酸乙酯 、 Petroleum ether 为溶剂， 以97%的产率得到(E)-4-methylbenzyl but-2-enoate
  参考文献：
  名称：

  Palladium-Catalyzed Carboxylative Coupling of Benzyl Chlorides with Allyltributylstannane: Remarkable Effect of Palladium Nanoparticles

  摘要：

  Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane was successfully conducted to produce benzyl but-3-enoates in satisfactory to good yields. The carboxylative coupling reaction occurred smoothly under mild conditions in the presence of palladium nanoparticles in tetrahydrofuran.

  DOI：

  10.1021/ol303135e
• 作为产物：
  描述：

  二氧化碳 、 烯丙基三丁基锡 、 4-甲基氯苄 在 bis(acetylacetonato)palladium(II) 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 以82%的产率得到4-methylbenzyl but-3-enoate
  参考文献：
  名称：

  Palladium-Catalyzed Carboxylative Coupling of Benzyl Chlorides with Allyltributylstannane: Remarkable Effect of Palladium Nanoparticles

  摘要：

  Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane was successfully conducted to produce benzyl but-3-enoates in satisfactory to good yields. The carboxylative coupling reaction occurred smoothly under mild conditions in the presence of palladium nanoparticles in tetrahydrofuran.

  DOI：

  10.1021/ol303135e

文献信息

• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• Carboxylative Suzuki coupling reactions of benzyl chlorides with allyl pinacolborate catalyzed by palladium nanoparticles
  作者：Jian Sun、Jiasheng Wang、Xiujuan Feng、Yoshinori Yamamoto、Abdulrahman I. Almansour、Natarajan Arumugam、Raju Suresh Kumar、Ming Bao

  DOI：10.1016/s1872-2067(18)63045-1

  日期：2018.7

  Abstract Palladium-catalyzed carboxylative Suzuki coupling reactions of benzyl chlorides with allyl pinacolborate were successfully conducted in the absence of any extra ligand to produce β,γ-unsaturated esters in satisfactory to good yields. The carboxylative Suzuki coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles generated in situ through the formation

  摘要 钯催化的苄基氯与频哪醇硼酸烯丙酯的羧化 Suzuki 偶联反应在没有任何额外配体的情况下成功进行，以令人满意的收率生产 β,γ-不饱和酯。在通过形成 π-苄基氯化钯中间体原位生成的钯纳米粒子的存在下，羧化 Suzuki 偶联反应在温和条件下顺利进行。
• 一种β,γ–不饱和酯化合物的制备方法
  申请人：大连理工大学

  公开号：CN105777463B

  公开（公告）日：2019-01-18

  本发明属于医药化工中间体及相关化学技术领域，涉及一种β,γ–不饱和酯化合物的制备方法。其特征是通过使用原位生成的过渡金属钯纳米粒子作为催化剂，实现卤代甲基(杂)芳烃化合物、烯丙基硼酸频哪醇酯以及二氧化碳三组分之间羧化反应，生成不饱和酯化合物。不饱和酯类化合物是一类非常重要的化学中间体，可用于合成多种非常有用的化合物。该方法操作简便、原料易得、环境友好，对二氧化碳的应用研究具有重要的意义。
• US8399684B2
  申请人：——

  公开号：US8399684B2

  公开（公告）日：2013-03-19
• Palladium-Catalyzed Carboxylative Coupling of Benzyl Chlorides with Allyltributylstannane: Remarkable Effect of Palladium Nanoparticles
  作者：Xiujuan Feng、Anle Sun、Sheng Zhang、Xiaoqiang Yu、Ming Bao

  DOI：10.1021/ol303135e

  日期：2013.1.4

  Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane was successfully conducted to produce benzyl but-3-enoates in satisfactory to good yields. The carboxylative coupling reaction occurred smoothly under mild conditions in the presence of palladium nanoparticles in tetrahydrofuran.