(1R,4R)-2-(4-methoxyphenyl)-5-phenylbicyclo[2.2.2]octa-2,5-diene | 1374793-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,4R)-2-(4-methoxyphenyl)-5-phenylbicyclo[2.2.2]octa-2,5-diene
• CAS: 1374793-27-7
• 化学式: C₂₁H₂₀O
• 分子量: 288.389
• InChiKey: JRGAITYMTRKDOW-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1R,2S,3S,4R)-6-oxo-3-phenylbicyclo[2.2.2]octan-2-yl methanesulfonate 在 2,4,6-三甲基吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 (1R,4R)-2-(4-methoxyphenyl)-5-phenylbicyclo[2.2.2]octa-2,5-diene
  参考文献：
  名称：

  Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands

  摘要：

  An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.

  DOI：

  10.1021/jo3005638

文献信息

• Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides
  作者：Lucas Vidal、Pan-Pan Chen、Eva Nicolas、Andrew Hackett、Craig M. Robertson、Kendall N. Houk、Christophe Aïssa

  DOI：10.1021/acs.orglett.2c03396

  日期：2022.11.25

  Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the re face of the olefin

  迄今为止，α-羰基亚砜 (SY) 的对映选择性环丙烷化仅限于缺电子烯烃的加成/闭环反应。在此，我们报道了在手性二烯存在下铱催化的 SY 分子内环丙烷化反应，收率高达 96%，对映选择性高达 98%。此外，密度泛函理论计算表明，烯烃的表面优选在与烯烃的几何结构无关的异步协同步骤中攻击铱卡宾中间体。
• Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands
  作者：Stefan Abele、Roman Inauen、Dirk Spielvogel、Christian Moessner

  DOI：10.1021/jo3005638

  日期：2012.5.18

  An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.