(S)-(+)-2-methyl-4-phenyl-2-pentene | 960403-37-6

• 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: (S)-(+)-2-methyl-4-phenyl-2-pentene
• 英文别名: [(2S)-4-methylpent-3-en-2-yl]benzene
• CAS: 960403-37-6
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: NKDQCWOVRPPHEF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-methyl-4-phenyl-2-pentene 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 (R)-(-)-2-苯基丙酸
  参考文献：
  名称：

  An Enantioselective Route to α-Methyl Carboxylic Acids via Metal and Enzyme Catalysis

  摘要：

  Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.

  DOI：

  10.1021/ol702261t
• 作为产物：
  描述：

  (R)-(+)-4-methylpent-3-en-2-yl acetate 、 phenylmagnesium bromide 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 4-methyl-4-phenyl-2-pentene 、 (S)-(+)-2-methyl-4-phenyl-2-pentene
  参考文献：
  名称：

  An Enantioselective Route to α-Methyl Carboxylic Acids via Metal and Enzyme Catalysis

  摘要：

  Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.

  DOI：

  10.1021/ol702261t

文献信息

• Remarkable Change of the Diastereoselection in the Dye-Sensitized Ene Hydroperoxidation of Chiral Alkenes by Zeolite Confinement
  作者：Manolis Stratakis、Dimitris Kalaitzakis、Dimitris Stavroulakis、Giannis Kosmas、Constantinos Tsangarakis

  DOI：10.1021/ol0352660

  日期：2003.9.1

  [GRAPHICS]The ene reaction of singlet oxygen with chiral trisubstituted alkenes bearing an alkyl and a phenyl group at the stereogenic center is erythro diastereoselective in solution and threo diastereoselective if carried out within zeolite Na-Y. The change of the diastereoselection trend by zeolite confinement is attributed to a synergism of steric effects and cation-pi interactions.
• An Enantioselective Route to α-Methyl Carboxylic Acids via Metal and Enzyme Catalysis
  作者：Jakob Norinder、Krisztián Bogár、Lisa Kanupp、Jan-E. Bäckvall

  DOI：10.1021/ol702261t

  日期：2007.11.1

  Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.