(1R)-myrtenyl phenyl ether | 1202554-04-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-myrtenyl phenyl ether
• CAS: 1202554-04-8
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: NBKQQZGNEGOWMX-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  溴苯 、 (-)-桃金娘烯醇 在 copper(l) iodide 、 N-([1,1'-biphenyl]-2-yl)-N′-(2-phenylnaphthalen-1-yl)benzene-1,2-diamine 、 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 生成 (1R)-myrtenyl phenyl ether
  参考文献：
  名称：

  Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides

  摘要：

  We disclose the development of a Cu‐catalyzed C−O coupling method utilizing a new N1,N2‐diarylbenzene‐1,2‐diamine ligand, L8. Under optimized reaction conditions, structurally diverse aryl and heteroaryl bromides underwent efficient coupling with a variety of alcohols at room temperature using an L8‐based catalyst. Notably, the L8‐derived catalyst exhibited enhanced activity when compared to the L4‐based system previously disclosed for C−N coupling, namely the ability to functionalize aryl bromides containing acidic functional groups. Mechanistic studies demonstrate that C−O coupling utilizing L8 ⋅ Cu involves rate‐limiting alkoxide transmetallation, resulting in a mechanism of C−O bond formation that is distinct from previously described Pd‐, Cu‐, or Ni‐based systems. This lower energy pathway leads to rapid C−O bond formation; a 7‐fold increase relative to what is seen with other ligands. The results presented in this report overcome limitations in previously described C−O coupling methods and introduce a new ligand that we anticipate may be useful in other Cu‐catalyzed C‐heteroatom bond‐forming reactions.

  DOI：

  10.1002/anie.202400333

文献信息

• New chiral selenium electrophiles derived from functionalized terpenes
  作者：Jacek Ścianowski、Zbigniew Rafiński、Aleksandra Szuniewicz、Andrzej Wojtczak

  DOI：10.1016/j.tet.2009.10.005

  日期：2009.12

  A convenient method for the synthesis of optically active dialkyl diselenides derived from bicyclic terpenes functionalized with hydroxy, etheral, sulfide, and selenide groups is described. The diselenides were used for a synthesis of chiral electrophilic selenium reagents, then in the asymmetric selenenylation of styrene and selenocyclization with o-allylphenol. The influence of nonbonding selenium-heteroatom

  描述了一种方便的合成旋光性二烷基二硒化物的方法，所述二烷基二硒化物衍生自被羟基，醚基，硫化物和硒基团官能化的双环萜烯。将二硒化物用于合成手性亲电子硒试剂，然后用于苯乙烯的不对称亚硒基化和与邻烯丙基苯酚的硒环化。研究了生成的有机硒亲电体中非键合的硒-杂原子相互作用对加成反应的立体选择性的影响。通过DFT方法在B3LYP（6-311G（d））水平上的计算，证实了所研究系统中存在非键合的硒-杂原子相互作用。