(2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanoic acid | 138603-03-9

• 英文名称: (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanoic acid
• CAS: 138603-03-9
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: FZSFLWXSLLIJPD-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanoic acid 以 乙醚 为溶剂， 生成 (-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019
• 作为产物：
  描述：

  (+/-)-1-cyclohexyl-2-methyl-2-propen-1-ol 在 咪唑 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 双氧水 、 对甲苯磺酸 、 silver nitrate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.67h， 生成 (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanoic acid
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• BLACK, T. HOWARD;DUBAY, WILLIAM J. (III);TULLY, PAUL S., J. ORG. CHEM., 53,(1988) N 25, C. 5922-5927
  作者：BLACK, T. HOWARD、DUBAY, WILLIAM J. (III)、TULLY, PAUL S.

  DOI：——

  日期：——