(1R,2R,5S)-2-Methyl-2-(morpholin-4-yl)-5-(prop-1-en-2-yl)cyclohexan-1-ol | 945681-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,5S)-2-Methyl-2-(morpholin-4-yl)-5-(prop-1-en-2-yl)cyclohexan-1-ol
• 英文别名: (1R,2R,5S)-2-methyl-2-morpholin-4-yl-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 945681-45-8
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: AYRKWHNLIKGDRV-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吗啉 、 (−)-氧化柠檬烯（顺反异构体混合物） 在 水 作用下， 反应 24.0h， 生成 (1R,2R,5S)-2-Methyl-2-(morpholin-4-yl)-5-(prop-1-en-2-yl)cyclohexan-1-ol 、 (1R,2R,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol
  参考文献：
  名称：

  Scale-Up of the Preparation of (1R,2R,4S)-1-Methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol

  摘要：

  Chiral beta-amino alcohols are widely recognized as effective chiral auxiliaries for a variety of asymmetric organic transformations. Recently, (1R,2R,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol has been reported to be an effective chiral auxiliary for the asymmetric addition of diethylzinc to benzaldehyde and the asymmetric addition of lithium cyclopropylacetylide to 4-(trifluoromethyl)-2(1H)-quinazolinones. This paper describes the scale-up of the reaction of morpholine with cis/trans-(S)-(-)-limonene oxide (99% ee) in the presence of water to produce 125 g of (1R,2R,4S)-1-methyl-4-(1-methylethenyl)2-(4-morpholinyl)cyclohexanol of 99.6% diastereomeric purity.

  DOI：

  10.1021/op700092n

文献信息

• Scale-Up of the Preparation of (1<i>R</i>,2<i>R</i>,4<i>S</i>)-1-Methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol
  作者：Christian T. Goralski、Dennis L. Hasha、Bakthan Singaram、Derek Steiner

  DOI：10.1021/op700092n

  日期：2007.7.1

  Chiral beta-amino alcohols are widely recognized as effective chiral auxiliaries for a variety of asymmetric organic transformations. Recently, (1R,2R,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol has been reported to be an effective chiral auxiliary for the asymmetric addition of diethylzinc to benzaldehyde and the asymmetric addition of lithium cyclopropylacetylide to 4-(trifluoromethyl)-2(1H)-quinazolinones. This paper describes the scale-up of the reaction of morpholine with cis/trans-(S)-(-)-limonene oxide (99% ee) in the presence of water to produce 125 g of (1R,2R,4S)-1-methyl-4-(1-methylethenyl)2-(4-morpholinyl)cyclohexanol of 99.6% diastereomeric purity.