(R)-(-)-3-(o-Anisyl)heptansaeure | 61198-45-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-(-)-3-(o-Anisyl)heptansaeure
• 英文别名: (3R)-3-(2-methoxyphenyl)heptanoic acid
• CAS: 61198-45-6
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: KNMYUWZXWRJHKJ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-(o-Anisyl)heptansaeure 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (R)-4-butylhydrocoumarin
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r
• 作为产物：
  描述：

  tert-butyl N-[(3R)-3-(2-methoxyphenyl)heptanoyl]-N-methylcarbamate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-(-)-3-(o-Anisyl)heptansaeure
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r

文献信息

• An asymmetric synthesis of 5-methoxy-3-substituted acids and their related lactones in high enantiomeric purity
  作者：A.I. Meyers、Charles E. Whitten

  DOI：10.1016/s0040-4039(00)78086-5

  日期：1976.6
• Highly stereoselective addition of organolithium reagents to chiral oxazolines. Asymmetric synthesis of 3-substituted alkanoic acids and 3-substituted lactones
  作者：A. I. Meyers、R. Keith Smith、Charles E. Whitten

  DOI：10.1021/jo01327a046

  日期：1979.6
• MEYERS A. I.; SMITH R. K.; WHITTEN C. E., J. ORG. CHEM., 1979, 44, NO 13, 2250-2256
  作者：MEYERS A. I.、 SMITH R. K.、 WHITTEN C. E.

  DOI：——

  日期：——
• MEYERS A. I.; WHITTEN C. E., TETRAHEDRON LETT. <TELE-AY>, 1976, NO 23, 1947-1950
  作者：MEYERS A. I.、 WHITTEN C. E.

  DOI：——

  日期：——
• Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions
  作者：Gary P. Lutz、Hua Du、Donald J. Gallagher、Peter Beak

  DOI：10.1021/jo952223r

  日期：1996.1.1

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.