(1R,2R,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol | 362665-87-0

• 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,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol
• 英文别名: (1R,2R,4S)-1-methyl-2-morpholin-4-yl-4-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 362665-87-0
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: YTJVBLPAMBTDCH-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：

  (1R,2R,4S)-1-methyl-4-(1-methylethenyl)cyclohexanol oxalate 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 以35.56 g的产率得到(1R,2R,4S)-1-methyl-4-(1-methylethenyl)-2-(4-morpholinyl)cyclohexanol
  参考文献：
  名称：

  Chiral amino alcohols and process for preparation of same

  摘要：

  所披露的发明包括具有以下结构的化合物：其中R1和R2分别表示氢或含有4个或更多碳原子的烷基基团。还披露了一种从起始胺化合物和柠檬烯氧制备所披露的手性氨基醇的方法。

  公开号：

  US06362373B1

文献信息

• Chiral amino alcohols and process for preparation of same
  申请人：The Dow Chemical Company

  公开号：US06362373B1

  公开（公告）日：2002-03-26

  The disclosed invention comprises a compound having the formula: in which R1 and R2 independently represent a hydrogen or an alkyl group of 4 carbon atoms or greater. Further disclosed is a process for the preparation of the disclosed chiral amino alcohols from a starting amine compound and a limonene oxide.

  所披露的发明包括具有以下结构的化合物：其中R1和R2分别表示氢或含有4个或更多碳原子的烷基基团。还披露了一种从起始胺化合物和柠檬烯氧制备所披露的手性氨基醇的方法。
• A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide
  作者：Will Chrisman、Jason N Camara、Kim Marcellini、Bakthan Singaram、Christian T Goralski、Dennis L Hasha、Philip R Rudolf、Lawrence W Nicholson、Karen K Borodychuk

  DOI：10.1016/s0040-4039(01)01135-2

  日期：2001.8

  A series of chiral β-amino alcohols was prepared by the reaction of secondary amines with a 1:1 mixture of cis- and trans-limonene oxide in the presence of water as a catalyst. The β-amino alcohol obtained was derived from the trans-limonene oxide, and the unreacted cis-limonene oxide was recovered from the reaction mixture. The β-amino alcohols are useful chiral auxiliaries for the addition of diethylzinc

  在水为催化剂的情况下，通过使仲胺与1：1的顺式和反式-柠檬烯氧化物混合物反应，制备了一系列手性β-氨基醇。所获得的β-氨基醇衍生自反式-柠檬烯氧化物，并且从反应混合物中回收未反应的顺式-柠檬烯氧化物。β-氨基醇是用于将二乙基锌加到苯甲醛中的有用的手性助剂。
• Asymmetric addition of diethylzinc to aldehydes catalyzed by β-amino alcohols derived from limonene oxide
  作者：Derek Steiner、Steven G. Sethofer、Christian T. Goralski、Bakthan Singaram

  DOI：10.1016/s0957-4166(02)00342-7

  日期：2002.8

  A series of β-amino alcohols, conveniently prepared from limonene oxide, were evaluated as catalysts for the enantioselective addition of dialkylzinc to benzaldehyde. These limonene-based amino alcohols are of particular interest because they are easily synthesized in both enantiomeric forms. Ethylation of benzaldehyde using diethylzinc and catalyzed by limonene derived amino alcohols proceeded with

  评价了一系列由氧化柠檬烯方便地制备的β-氨基醇，作为将二烷基锌对苯甲醛对映选择性加成的催化剂。这些基于柠檬烯的氨基醇特别令人感兴趣，因为它们易于以两种对映体形式合成。使用二乙基锌对苯甲醛进行乙基化并由柠檬烯衍生的氨基醇进行催化，对映体分离度最高可达ee的87％。对于具有氨基和醇官能度之间的反式关系的氨基醇，这是异常高的诱导水平。1-苯基-1-丙醇的两种对映异构体可以在相同的控制下合成，因为手性催化剂的两种对映异构体都是容易获得的。当（1 S，2 S，4 R）-柠檬烯氨基醇用作手性催化剂，（R）-1-苯基-1-丙醇为主要产物。提出了一种合理的机制来解释面部选择性，这些面部选择性决定了在这些反应中观察到的不对称诱导。
• US6362373B1
  申请人：——

  公开号：US6362373B1

  公开（公告）日：2002-03-26
• 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.