(2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal | 138490-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal
• CAS: 138490-51-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: RZIDYHIPLPRCBQ-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal 在 sodium hydroxide 、 silver nitrate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 4.0h， 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 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.67h， 生成 (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal
  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

• Catalytic Asymmetric Iterative/Domino Aldehyde Cross-Aldol Reactions for the Rapid and Flexible Synthesis of 1,3-Polyols
  作者：Luqing Lin、Kumiko Yamamoto、Harunobu Mitsunuma、Yamato Kanzaki、Shigeki Matsunaga、Motomu Kanai

  DOI：10.1021/jacs.5b11192

  日期：2015.12.16

  aldehydes and stereoselectivity can be flexibly switched in a stepwise manner for the double-aldol reaction. Furthermore, asymmetric triple- and quadruple-aldol reactions are possible in one-pot using the appropriate amounts of donors and amine additives, rapidly elongating the carbon skeleton with controlling up to eight stereocenters. The method should be useful for straightforward synthesis of enantiomerically

  我们在这里报告了醛之间的催化不对称迭代和多米诺交叉羟醛反应，具有高度的稳健性、灵活性和通用性。Cu(I)-DTBM-SEGPHOS 复合物催化受体醛和由供体醛衍生的硼烯醇化物之间的不对称交叉羟醛反应，该反应是通过 Ir 催化的烯丙氧基硼酸酯异构化产生的。可以重复使用醛醇产物作为随后不对称醛醇反应的受体底物的单元过程。双醇醛反应的供体醛和立体选择性可以以逐步的方式灵活切换。此外，使用适量的供体和胺添加剂，可以在一锅法中进行不对称的三重和四重醛醇反应，通过控制多达八个立体中心快速拉长碳骨架。该方法可用于直接合成对映异构和非对映异构富集的 1,3-多元醇。
• Direct catalytic asymmetric cross-aldol reactions in ionic liquid media
  作者：Armando Córdova

  DOI：10.1016/j.tetlet.2004.03.080

  日期：2004.5

  Enantioselective proline-catalyzed direct asymmetric cross-aldol reactions with aldehydes were performed in ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate media, which simplified product isolation and catalyst recycling, affording 3-hydroxy aldehydes in high yield with excellent stereoselectivity. In addition, the enhanced reactivity of the asymmetric cross-aldol reactions in ionic

  在离子液体1-正丁基-3-甲基咪唑鎓六氟磷酸酯介质中进行对映选择性脯氨酸催化的与醛类的直接不对称交叉醛醇缩合反应，简化了产物的分离和催化剂的循环利用，以高收率提供了3-羟基醛，并具有出色的立体选择性。另外，在离子液体中不对称交叉醛醇缩合反应的增强的反应性使得催化剂的负载显着降低。