(S)-3,4a-dimethyl-6-phenyl-4a,5-dihydronaphthalene-1,4-dione | 1567408-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3,4a-dimethyl-6-phenyl-4a,5-dihydronaphthalene-1,4-dione
• 英文别名: (4aS)-3,4a-dimethyl-6-phenyl-5H-naphthalene-1,4-dione
• CAS: 1567408-44-9
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: LXHVTXBKKLPRMX-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-苯基丁醛 、 2,6-二甲基-2,5-环己二烯-1,4-二酮 在 2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine 、 氧气 、 palladium diacetate 、 邻氟苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 以70%的产率得到(S)-3,4a-dimethyl-6-phenyl-4a,5-dihydronaphthalene-1,4-dione
  参考文献：
  名称：

  Enantioselective Functionalization of Inactive sp³ C–H Bonds Remote to Functional Group by Metal/Organo Cooperative Catalysis

  摘要：

  A metal/organo cooperative catalysis to enable the enantioselective functionalization of inactive C-H bonds gamma to the formyl group in aliphatic aldehydes has been established. Instead of using enals as substrates in traditional organocatalytic cydization reactions, the aliphatic aldehydes directly participated in [4 + 2] cyclization with quinone derivatives exploiting molecular oxygen as oxidants to afford optically active cyclic molecules with excellent levels of enantioselectivity. This method features a combination of pot, step, and atom economy.

  DOI：

  10.1021/acs.orglett.5b02653

文献信息

• Organocatalytic Enantioselective Cycloaddition Reactions of Dienamines with Quinones
  作者：Tore Kiilerich Johansen、Clarisa Villegas Gómez、Jesper R. Bak、Rebecca L. Davis、Karl Anker Jørgensen

  DOI：10.1002/chem.201303526

  日期：2013.12.2

  Matching catalyst and substrate: Organocatalytic cycloaddition between dienamines and 1,4‐benzo‐ or 1,4‐naphthoquinones affords biologically interesting dihydronaphtho‐ and dihydroanthraquinone core structures. The enantioselectivity of this new reaction is ensured by a steric shielding catalyst and carefully selecting substrates that greatly favor the endo approach (see scheme) due to electrostatic

  匹配的催化剂和底物：二烯胺和1,4-苯并或1,4-萘醌之间的有机催化环加成反应提供了生物学上令人感兴趣的二氢萘和二氢蒽醌核心结构。该新反应的对映选择性是通过空间屏蔽催化剂和精心选择的底物来确保的，该底物由于两性离子中间体中的静电相互作用而极大地支持了内切法（参见方案）。
• Enantioselective Functionalization of Inactive sp³ C–H Bonds Remote to Functional Group by Metal/Organo Cooperative Catalysis
  作者：Xiao-Le Zhou、Pu-Sheng Wang、Da-Wei Zhang、Peng Liu、Cheng-Ming Wang、Liu-Zhu Gong

  DOI：10.1021/acs.orglett.5b02653

  日期：2015.10.16

  A metal/organo cooperative catalysis to enable the enantioselective functionalization of inactive C-H bonds gamma to the formyl group in aliphatic aldehydes has been established. Instead of using enals as substrates in traditional organocatalytic cydization reactions, the aliphatic aldehydes directly participated in [4 + 2] cyclization with quinone derivatives exploiting molecular oxygen as oxidants to afford optically active cyclic molecules with excellent levels of enantioselectivity. This method features a combination of pot, step, and atom economy.