(S)-α-(2-naphthyl)-δ-valerolactone | 1330660-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-α-(2-naphthyl)-δ-valerolactone
• 英文别名: (S)-3-(naphthalen-2-yl)tetrahydro-2H-pyran-2-one；(3S)-3-naphthalen-2-yloxan-2-one
• CAS: 1330660-83-7
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: LXPSRCHIOIBLHB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-萘硼酸 在 [((CH₃)2C(C₃H₃NOC₆H₅)2)Cu(OSO₂CF₃)] 、 (CuOTf)2PhMe 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 14.67h， 生成 (S)-α-(2-naphthyl)-δ-valerolactone
  参考文献：
  名称：

  Enantioselective α-Arylation of Carbonyls via Cu(I)-Bisoxazoline Catalysis

  摘要：

  The enantioselective alpha-arylation of both lactones and acyl oxazolidones has been accomplished using a combination of diaryliodonium salts and copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-carbonyl benzylic stereocenters, a valuable synthon for the production of medicinal agents.

  DOI：

  10.1021/ja206050b

文献信息

• Weak Arene CH⋅⋅⋅O Hydrogen Bonding in Palladium-Catalyzed Arylation and Vinylation of Lactones
  作者：Zhiyan Huang、Zuliang Chen、Li Hui Lim、Gia Chuong Phan Quang、Hajime Hirao、Jianrong Steve Zhou

  DOI：10.1002/anie.201300481

  日期：2013.5.27

  Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH⋅⋅⋅O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH⋅⋅⋅O hydrogen bonding to guide stereoselection.

  作用力弱：在标题反应中，钯催化剂（参见左图）使用弱的CH⋅⋅⋅O氢键控制新立体中心的绝对构型。类似的钯催化剂（右）使用常规的NH····O氢键来引导立体选择。
• Enantioselective α-Arylation of Carbonyls via Cu(I)-Bisoxazoline Catalysis
  作者：James S. Harvey、Scott P. Simonovich、Christopher R. Jamison、David W. C. MacMillan

  DOI：10.1021/ja206050b

  日期：2011.9.7

  The enantioselective alpha-arylation of both lactones and acyl oxazolidones has been accomplished using a combination of diaryliodonium salts and copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-carbonyl benzylic stereocenters, a valuable synthon for the production of medicinal agents.