(R)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester | 220168-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-methoxy-2-naphthalen-1-ylpropanoate
• CAS: 220168-00-3
• 化学式: C₂₄H₃₂O₃
• 分子量: 368.516
• InChiKey: CWNZAVXNYDOTDD-KSZDXEJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (R)-(-)-2-甲氧基-2-(1-萘基)丙酸
  参考文献：
  名称：

  2-Methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for enantioresolution of alcohols and determination of their absolute configurations by the 1H NMR anisotropy method

  摘要：

  Racemic 2-methoxy-2-(l-naphthyl)propionic acid (1, M alpha NP acid) was enantioresolved as its esters derived from various chiral alcohols. For example, a diastereomeric mixture of esters prepared from (+/-)-1 and (1R,3R,4S)-(-)-menthol was easily separated by HPLC on silica gel yielding esters (-)-2a and (-)-2b, the separation factor alpha = 1.83 being unusually large. The H-1 NMR chemical shift differences, Delta delta = delta(R)-delta(S), between diastereomers 2a and 2b, are much larger than those of conventional chiral auxiliaries, e.g. Mosher's MTPA and Trost's MPA acids. This acid 1 is therefore very powerful for determining the absolute configuration of chiral alcohols by the H-1 NMR anisotropy method. Solvolysis of the separated esters yielded enantiopure acids (S)-(+)-1 and (R)-(-)-1, which are useful for enantioresolution of racemic alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00053-7
• 作为产物：
  描述：

  L-薄荷醇 、 2-甲氧基-2-(1-萘基)丙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  2-Methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for enantioresolution of alcohols and determination of their absolute configurations by the 1H NMR anisotropy method

  摘要：

  Racemic 2-methoxy-2-(l-naphthyl)propionic acid (1, M alpha NP acid) was enantioresolved as its esters derived from various chiral alcohols. For example, a diastereomeric mixture of esters prepared from (+/-)-1 and (1R,3R,4S)-(-)-menthol was easily separated by HPLC on silica gel yielding esters (-)-2a and (-)-2b, the separation factor alpha = 1.83 being unusually large. The H-1 NMR chemical shift differences, Delta delta = delta(R)-delta(S), between diastereomers 2a and 2b, are much larger than those of conventional chiral auxiliaries, e.g. Mosher's MTPA and Trost's MPA acids. This acid 1 is therefore very powerful for determining the absolute configuration of chiral alcohols by the H-1 NMR anisotropy method. Solvolysis of the separated esters yielded enantiopure acids (S)-(+)-1 and (R)-(-)-1, which are useful for enantioresolution of racemic alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00053-7

文献信息

• 2-Methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for enantioresolution of alcohols and determination of their absolute configurations by the 1H NMR anisotropy method
  作者：Nobuyuki Harada、Masataka Watanabe、Shunsuke Kuwahara、Akinori Sugio、Yusuke Kasai、Akio Ichikawa

  DOI：10.1016/s0957-4166(00)00053-7

  日期：2000.4

  Racemic 2-methoxy-2-(l-naphthyl)propionic acid (1, M alpha NP acid) was enantioresolved as its esters derived from various chiral alcohols. For example, a diastereomeric mixture of esters prepared from (+/-)-1 and (1R,3R,4S)-(-)-menthol was easily separated by HPLC on silica gel yielding esters (-)-2a and (-)-2b, the separation factor alpha = 1.83 being unusually large. The H-1 NMR chemical shift differences, Delta delta = delta(R)-delta(S), between diastereomers 2a and 2b, are much larger than those of conventional chiral auxiliaries, e.g. Mosher's MTPA and Trost's MPA acids. This acid 1 is therefore very powerful for determining the absolute configuration of chiral alcohols by the H-1 NMR anisotropy method. Solvolysis of the separated esters yielded enantiopure acids (S)-(+)-1 and (R)-(-)-1, which are useful for enantioresolution of racemic alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.