(E)-2-(3-(4-(hydroxymethyl)phenyl)allyl)cyclohexanone | 1579255-36-9

• 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: (E)-2-(3-(4-(hydroxymethyl)phenyl)allyl)cyclohexanone
• 英文别名: (E)-2-(3-(4-(hydroxymethyl)phenyl)allyl)cyclohexan-1-one；2-[(E)-3-[4-(hydroxymethyl)phenyl]prop-2-enyl]cyclohexan-1-one
• CAS: 1579255-36-9
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: ZKYBXZWZBIFOKO-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-溴苯基)丙-2-烯-1-醇 在 四氢吡咯 、 1,1'-双(二苯基膦)二茂铁 、 sodium tetrahydroborate 、 正丁基锂 、 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.67h， 生成 (E)-2-(3-(4-(hydroxymethyl)phenyl)allyl)cyclohexanone
  参考文献：
  名称：

  Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

  摘要：

  C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

  DOI：

  10.1021/ol5000988

文献信息

• Cooperativity between the Substrate and Ligand in Palladium-Catalyzed Allylic Alkylation Using 1-Aryl-1-propynes
  作者：Aniket Gupta、Anusuya Saha、Ajijur Rahaman、Jogendra Kumar、Eringathodi Suresh、Bishwajit Ganguly、Sukalyan Bhadra

  DOI：10.1021/acs.joc.2c00592

  日期：2022.8.5

  a variety of ketones, β-keto esters, aldehydes, etc., during enamine–palladium catalysis. Density functional theory calculations reveal that Bz-Gly-OH assists in the formation of an enamine that attacks the π-allylpalladium complex via an outer sphere mechanism. The preliminary result points to an asymmetric allylic alkylation under a new mode of bifunctional catalysis.

  在烯胺-钯催化过程中，单保护氨基酸 Bz-Gly-OH 有助于各种酮、β-酮酯、醛等的烯丙基烷基化。密度泛函理论计算表明，Bz-Gly-OH 有助于形成烯胺，该烯胺通过外球机制攻击 π-烯丙基钯络合物。初步结果表明在双功能催化新模式下的不对称烯丙基烷基化。