(3R,4S)-3,4-dihydroxy-4-(naphthalen-1-yl)butan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4S)-3,4-dihydroxy-4-(naphthalen-1-yl)butan-2-one
• 英文别名: (3R,4S)-4-(1-naphthyl)-3,4-dihydroxybutan-2-one；(3R,4S)-3,4-dihydroxy-4-naphthalen-1-ylbutan-2-one
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: DRGYAVRIGUVIGP-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-萘甲醛 、 羟基丙酮 在 (2S,3R)-O-(n-octanoyl)-L-threonine 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 96.0h， 生成 (3R,4S)-3,4-dihydroxy-4-(naphthalen-1-yl)butan-2-one 、 4-(1-naphthyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone

  摘要：

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.022

文献信息

• Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds
  作者：Ling-Yu Li、Da-Cheng Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2015.01.061

  日期：2015.3

  The catalytic promiscuity of pepsin from porcine gastric mucous was observed in catalysis of the direct asymmetric aldol reactions of aromatic aldehydes with acetones, which were substituted by hydroxy-, dihydroxy-, methoxy- and benzyloxy- for the synthesis of diol compounds in acetonitrile. This biocatalysis was also applicable to the aldol reactions of cyclic or hetereocyclic ketones with aromatic

  在催化芳香族醛与丙酮直接不对称醛醇缩合反应的催化过程中，观察到了胃蛋白酶对胃蛋白酶的混杂作用，丙酮醛被羟基，二羟基，甲氧基和苄氧基所取代，从而在乙腈中合成二醇化合物。该生物催化也适用于环状或杂环酮与芳族醛的醛醇缩合反应。获得了高达87％的产率，高达> 99/1 dr的非对映选择性和高达75％ee的对映选择性。
• Direct Catalytic Asymmetric Synthesis of <i>anti</i>-1,2-Amino Alcohols and <i>syn</i>-1,2-Diols through Organocatalytic <i>anti</i>-Mannich and <i>syn</i>-Aldol Reactions
  作者：S. S. V. Ramasastry、Haile Zhang、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1021/ja0677012

  日期：2007.1.1

  anti-1,2-amino alcohols and syn-1,2-diols through direct asymmetric Mannich, Mannich-type, and aldol reactions involving unmodified α-hydroxyketones in reactions catalyzed by primary amine-containing amino acids. These reactions exploit (Z)-enamines of α-hydroxyketones in their bond-forming transition states. This study compliments and extends our bioorganic approach to asymmetric synthesis in these two

  手性 1,2-氨基醇和 1,2-二醇是在大量天然和生物活性分子中发现的常见结构基序。已经报道了使用基于金属的策略有效对映选择性合成含有顺-或反-1,2-氨基醇和1,2-二醇的酮。然而，迄今为止，涉及有机催化的方法仅限于合成 1,2-氨基醇和反 1,2-二醇。在此，我们公开了通过直接不对称曼尼希、曼尼希型和羟醛反应（涉及未修饰的 α-羟基酮在伯胺催化的反应中）制备高度对映体富集的抗 1,2-氨基醇和合成 1,2-二醇的简单有效途径-含氨基酸。这些反应利用处于成键过渡态的 α-羟基酮的 (Z)-烯胺。这项研究补充并扩展了我们在这两种多功能合成子类中进行不对称合成的生物有机方法。值得注意的是，这些反应是实用的，耐受湿溶剂，并且...
• Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tetasy.2011.06.022

  日期：2011.5

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.