O-myristoyl-trans-4-hydroxy-L-proline

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-myristoyl-trans-4-hydroxy-L-proline
• 英文别名: (2S,4R)-4-tetradecanoyloxypyrrolidine-2-carboxylic acid
• 化学式: C₁₉H₃₅NO₄
• 分子量: 341.491
• InChiKey: YDBRZZUVKBZHHL-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  O-myristoyl-trans-4-hydroxy-L-proline hydrochloride 在 methyloxirane 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 O-myristoyl-trans-4-hydroxy-L-proline
  参考文献：
  名称：

  Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst

  摘要：

  We report the aldol addition of acetone to aromatic aldehydes in the presence of a large amount of water where the stereochemical outcome of the reactions can be tuned with achiral salt additives using a single proline-derived catalyst. Depending on the nature of the added salt the (R) and (S) enriched products could be obtained. In the reaction of 2-nitrobenzaldehyde with acetone, NaOAc promoted the formation of the (S)-enantiomer (20% ee) while using NH4Cl the (R)-enantiomer was obtained in excess (58% ee). A similar inversion was observed for several other aromatic aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.051

文献信息

• Dual stereocontrol in aldol reactions catalysed by hydroxyproline derivatives in the presence of a large amount of water
  作者：András A. Gurka、Kornél Szőri、Mihály Bartók、Gábor London

  DOI：10.1016/j.tetasy.2016.08.009

  日期：2016.10

  Parameters influencing dual stereocontrol in aldol reactions of water miscible acetone with aromatic aldehydes in the presence of a large amount of water using hydroxyproline based catalysts were studied. Stereocontrol was achieved by changing the acidity and basicity of the reaction media by the addition of achiral salts in the presence of a single chiral catalyst. Under acidic conditions (NH4Cl salt) the (R)-aldol product was formed in excess while basic aqueous media (carboxylate salts) led to the enrichment of the (S)-enantiomer. Reaction conditions under which the reaction is feasible were optimised and the effect of the structure of the hydroxyproline-based catalysts was investigated. The results show that the formation of a biphasic micellar system and the presence of an appropriate catalyst are both crucial for the reaction to occur. Although the catalyst structure influenced the formation and stabilisation of the micellar system to a large extent, its effect on the enantioselectivities were found to be less pronounced. (C) 2016 Elsevier Ltd. All rights reserved.
• Tuning the sense of product stereochemistry in aldol reactions of acetone and aromatic aldehydes in the presence of water with a single chiral catalyst
  作者：András A. Gurka、Kornél Szőri、György Szőllősi、Mihály Bartók、Gábor London

  DOI：10.1016/j.tetlet.2015.11.051

  日期：2015.12

  We report the aldol addition of acetone to aromatic aldehydes in the presence of a large amount of water where the stereochemical outcome of the reactions can be tuned with achiral salt additives using a single proline-derived catalyst. Depending on the nature of the added salt the (R) and (S) enriched products could be obtained. In the reaction of 2-nitrobenzaldehyde with acetone, NaOAc promoted the formation of the (S)-enantiomer (20% ee) while using NH4Cl the (R)-enantiomer was obtained in excess (58% ee). A similar inversion was observed for several other aromatic aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.