O-(n-octanoyl)-L-threonine hydrochloride | 1256160-94-7

• 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-(n-octanoyl)-L-threonine hydrochloride
• 英文别名: (2S,3R)-2-amino-3-octanoyloxybutanoic acid;hydrochloride
• CAS: 1256160-94-7
• 化学式: C₁₂H₂₃NO₄*ClH
• 分子量: 281.78
• InChiKey: FZNJVPHHYRFYCK-XQKZEKTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  89.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-苏氨酸 、 辛酰氯 在 三氟乙酸 作用下， 反应 6.0h， 以95%的产率得到O-(n-octanoyl)-L-threonine hydrochloride
  参考文献：
  名称：

  苏氨酸表面活性剂有机催化剂，用于羟丙酮的高度非对映和对映选择性的直接抗曼尼希反应

  摘要：

  在这项工作中，第一步是在室温下将苏氨酸与酰氯在三氟乙酸中大规模反应而没有涉及的保护基团或色谱技术，一次合成了几种新的作为有机催化剂的l-苏氨酸衍生物。苏氨酸表面活性剂有机催化剂介导了羟基丙酮和苯胺与醛的直接不对称抗曼尼希反应，以高收率（75-93％）和高对映选择性（高达99％ee）合成抗-1,2-氨基醇。

  DOI：

  10.1016/j.tetlet.2010.08.085
• 作为试剂：
  描述：

  间硝基苯甲醛 、 4-甲基环己酮 在 O-(n-octanoyl)-L-threonine hydrochloride 、 水 、 三乙胺 作用下， 反应 24.0h， 以97%的产率得到(2S,4S)-2-((R)-hydroxy(3-nitrophenyl)methyl)-4-methylcyclohexan-1-one
  参考文献：
  名称：

  One-step, efficient synthesis of combined threonine–surfactant organocatalysts for the highly enantioselective direct aldol reactions of cyclic ketones with aromatic aldehydes in the presence of water

  摘要：

  In this work a new class of organocatalysts have been designed and synthesized in one step by a rational combination of threonine with acyl chlorides at room temperature in trifluoroacetic acid to make a series of novel combined threonine-surfactant organocatalysts readily available on a large-scale No protecting groups or chromatographic techniques are Involved in the procedures while certain combined threonine-surfactant organocatalysts mediate the direct aldol reactions of cyclic ketones with aromatic aldehydes to provide the aldol products in good yields with enantioselectivities of up to 99% (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.09.006

文献信息

• One-step, efficient synthesis of combined threonine–surfactant organocatalysts for the highly enantioselective direct aldol reactions of cyclic ketones with aromatic aldehydes in the presence of water
  作者：Chuanlong Wu、Xiangkai Fu、Xuebing Ma、Shi Li

  DOI：10.1016/j.tetasy.2010.09.006

  日期：2010.10

  In this work a new class of organocatalysts have been designed and synthesized in one step by a rational combination of threonine with acyl chlorides at room temperature in trifluoroacetic acid to make a series of novel combined threonine-surfactant organocatalysts readily available on a large-scale No protecting groups or chromatographic techniques are Involved in the procedures while certain combined threonine-surfactant organocatalysts mediate the direct aldol reactions of cyclic ketones with aromatic aldehydes to provide the aldol products in good yields with enantioselectivities of up to 99% (C) 2010 Elsevier Ltd All rights reserved
• Threonine-surfactant organocatalysts for the highly diastereo- and enantioselective direct anti-Mannich reactions of hydroxyacetone
  作者：Chuanlong Wu、Xiangkai Fu、Xuebing Ma、Shi Li、Chao Li

  DOI：10.1016/j.tetlet.2010.08.085

  日期：2010.11

  by the reaction of threonine with acyl chlorides at room temperature in trifluoroacetic acid on a large-scale without protecting groups involved or chromatographic techniques, and those threonine-surfactant organocatalysts mediated the direct asymmetric anti-Mannich reactions of hydroxyacetone and anilines with aldehydes to synthesize anti-1,2-amino alcohols in good yields (75–93%) and highly enantioselectivities

  在这项工作中，第一步是在室温下将苏氨酸与酰氯在三氟乙酸中大规模反应而没有涉及的保护基团或色谱技术，一次合成了几种新的作为有机催化剂的l-苏氨酸衍生物。苏氨酸表面活性剂有机催化剂介导了羟基丙酮和苯胺与醛的直接不对称抗曼尼希反应，以高收率（75-93％）和高对映选择性（高达99％ee）合成抗-1,2-氨基醇。