methyl 2-hydroxy-5-phenylpentanoate | 182918-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-hydroxy-5-phenylpentanoate
• 英文别名: Methyl-2-hydroxy-5-phenylpentanoat；2-hydroxy-5-phenyl-pentanoic acid methyl ester
• CAS: 182918-92-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: RFHCTDQZRLDGQU-UHFFFAOYSA-N

物化性质

• 沸点：
  330.9±35.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-5-phenylpentanoate 在 戴斯-马丁氧化剂 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-oxo-5-phenylpentanoate
  参考文献：
  名称：

  α-酮酯的有机催化对映选择性 Pictet-Spengler 反应：开发及其在 (+)-Alstratine A 全合成中的应用

  摘要：

  在催化量的手性丙氨酸衍生角酰胺和 4-硝基苯甲酸存在下，色胺与 α-酮酯反应得到相应的 1-烷基-1-甲氧基羰基四氢-β-咔啉 (THBC)，产率和ee值。笼状六环吲哚生物碱 alstratine A 的简明七步不对称全合成以这种对映选择性 Pictet-Spengler 反应为关键步骤。

  DOI：

  10.1002/anie.202213831
• 作为产物：
  描述：

  Methyl 5-(2-phenylethyl)-2-sulfanylidene-1,3-dioxolane-4-carboxylate 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到methyl 2-hydroxy-5-phenylpentanoate
  参考文献：
  名称：

  Regioselective Deoxygenation of the Cyclic Thionocarbonates of 2,3-Dihydroxy Esters with Magnesium in Methanol

  摘要：

  Deoxygenation of the cyclic thionocarbonates of 2,3-dihydroxy esters was mediated with magnesium iii methanol, which provided a facile method for the synthesis of or,hydroxy esters.

  DOI：

  10.1080/00397919908086456

文献信息

• Potent and Selective Fluoroketone Inhibitors of Group VIA Calcium-Independent Phospholipase A₂
  作者：George Kokotos、Yuan-Hao Hsu、John E. Burke、Constantinos Baskakis、Christoforos G. Kokotos、Victoria Magrioti、Edward A. Dennis

  DOI：10.1021/jm901872v

  日期：2010.5.13

  Group VIA calcium-independent phospholipase A2 (GVIA iPLA2) has recently emerged as a novel pharmaceutical target. We have now explored the structure−activity relationship between fluoroketones and GVIA iPLA2 inhibition. The presence of a naphthyl group proved to be of paramount importance. 1,1,1-Trifluoro-6-(naphthalen-2-yl)hexan-2-one (FKGK18) is the most potent inhibitor of GVIA iPLA2 (XI(50) =

  VIA 组钙非依赖性磷脂酶 A 2 (GVIA iPLA 2 ) 最近已成为一种新的药物靶点。我们现在已经探索了氟酮和 GVIA iPLA 2抑制之间的构效关系。萘基的存在被证明是极其重要的。1,1,1-Trifluoro-6-(naphthalen-2-yl)hexan-2-one (FKGK18) 是迄今为止报道的最有效的 GVIA iPLA 2抑制剂( X I (50) = 0.0002)。GVIA iPLA 2的效力分别是 GIVA cPLA 2和 GV sPLA 2 的195 倍和 >455 倍，使其成为探索 GVIA iPLA 2作用的宝贵工具在细胞和体内模型中。1,1,1,2,2,3,3-Heptafluoro-8-(naphthalene-2-yl)octan-4-one 抑制 GVIA iPLA 2，X I (50) 值为 0.001，同时抑制其他细胞内 GIVA cPLA
• PERFLUOROKETONE COMPOUNDS AND USES THEREOF
  申请人：David Samuel

  公开号：US20100048727A1

  公开（公告）日：2010-02-25

  Novel perfluoroketone compounds of formula [I] and [Ia] are described. Also described are uses thereof, such as for inhibition of phospholipase A 2 activity. Therapeutic uses thereof are also described, such as for the treatment of neural conditions and/or inflammatory conditions, such as demyelinating (e.g., multiple sclerosis) and neural injury (e.g., spinal cord injury).

  本文描述了化学式[I]和[Ia]的新型全氟酮化合物。还描述了它们的用途，例如用于抑制磷脂酶A2活性。还描述了它们的治疗用途，例如用于治疗神经疾病和/或炎症疾病，如脱髓鞘（例如多发性硬化症）和神经损伤（例如脊髓损伤）。
• PROCESS FOR PRODUCING 1,2-ETHANEDIOL DERIVATIVES
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0816316A1

  公开（公告）日：1998-01-07

  A process for preparing a 1,2-ethanediol derivative in a high yield by reducing an α-hydroxy carboxylic acid ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium boron hydride compound. A process for preparing a 1,2-ethanediol derivative in a high yield by esterifying an α-hydroxy carboxylic acid derivative to synthesize an α-hydroxy carboxylic acid ester derivative, and reducing this ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium borohydride compound in the same reaction vessel.

  一种在氢化硼钠化合物存在下，通过在原生溶剂或含水非丙烯极性溶剂中还原 α-羟基羧酸酯衍生物，以高产率制备 1，2-乙二醇衍生物的工艺。一种通过酯化α-羟基羧酸衍生物合成α-羟基羧酸酯衍生物，并在同一反应容器中，在有硼氢化钠化合物存在的情况下，在质子溶剂或含水非丙烷极性溶剂中还原该酯衍生物，从而高产率制备1，2-乙二醇衍生物的工艺。
• Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes
  作者：Constantinos Baskakis、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm800649q

  日期：2008.12.25

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.
• WO2008/122119
  申请人：——

  公开号：——

  公开（公告）日：——