ethyl 2-benzyl-3-oxopentanoate | 534599-79-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-benzyl-3-oxopentanoate
• 英文别名: Ethyl 2-benzyl-3-oxopentanoate
• CAS: 534599-79-6
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: MXFDUUDGNGSGDD-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±22.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-benzyl-3-oxopentanoate 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 3-benzyl-4-ethyl-2-oxo-2H-chromen-7-yl acetate
  参考文献：
  名称：

  Substituted 3-Benzylcoumarins as Allosteric MEK1 Inhibitors: Design, Synthesis and Biological Evaluation as Antiviral Agents

  摘要：

  为了寻找新型抗病毒药物，设计并合成了一系列别构MEK1抑制剂。基于对接结果，对香豆素支架进行了多次优化。某些衍生物在适当的酶学测定中表现出优秀的MEK1结合亲和力，并在细胞测定中对ERK通路表现出明显的抑制效应。这些化合物还显著抑制了HEK293和RD细胞中的病毒（EV71）复制。几种化合物显示出作为病毒感染性疾病治疗剂的潜力，其中最有效的化合物18在MEK1结合测定中的IC50值为54.57 nM。

  DOI：

  10.3390/molecules18056057
• 作为产物：
  描述：

  碘苯 、 ethyl 3-hydroxy-2-methylidenepentanoate 在 [5-Cl-2-{(4-Cl-phenyl)-[(E)-HO-imino]methyl}phenyl-PdCl]2 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以87%的产率得到ethyl 2-benzyl-3-oxopentanoate
  参考文献：
  名称：

  Nájera oxime-derived palladacycles catalyze intermolecular Heck reaction with Morita–Baylis–Hillman adducts. An improved and highly efficient synthesis of α-benzyl-β-ketoesters

  摘要：

  An improved and highly efficient synthesis of several alpha-benzyl-beta-ketoesters from Morita-Baylis-Hillman adducts is described. These adducts were used as substrates for an intermolecular Heck reaction catalyzed by a Najera oxime-derived palladacycles. These efficient catalytic conditions probed to be very selective providing only the corresponding functionalized beta-ketoesters in high yield with no decarboxylation product. It seems that the method herein described is one of the most efficient for the synthesis of alpha-benzyl-beta-ketoesters. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.084

文献信息

• Catalytic asymmetric construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements
  作者：Wande Zhang、Shiqiang Wei、Wenyao Wang、Jingping Qu、Baomin Wang

  DOI：10.1039/d1cc01123e

  日期：——

  An organocatalytic asymmetric process was reported for the sterically precise construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements. A series of interesting products featuring the union of a centrally chiral pyrazolone moiety and an axially chiral styrene unit were obtained in high yield with excellent diastereoselectivity and enantioselectivity (up to 99% ee

  报道了一种有机催化不对称过程，用于空间精确构建带有多个立体元素的 C-4 烯基取代的吡唑啉酮衍生物。以高产率获得了一系列有趣的产品，这些产品具有中心手性吡唑啉酮部分和轴向手性苯乙烯单元的结合，具有出色的非对映选择性和对映选择性（高达 99% ee，>20:1 dr）。该工艺具有反应条件温和、操作简单、底物适用范围广的特点。克级反应结果表明该反应具有良好的实用性。
• 6-Biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibited HIV reverse transcriptase-associated RNase H
  作者：Lei Wang、Jing Tang、Andrew D. Huber、Mary C. Casey、Karen A. Kirby、Daniel J. Wilson、Jayakanth Kankanala、Michael A. Parniak、Stefan G. Sarafianos、Zhengqiang Wang

  DOI：10.1016/j.ejmech.2018.07.035

  日期：2018.8

  Human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated ribonuclease H (RNase H) remains an unvalidated drug target. Reported HIV RNase H inhibitors generally lack significant antiviral activity. We report herein the design, synthesis, biochemical and antiviral evaluations of a new 6-biphenylmethyl subtype of the 3-hydroxypyrimidine-2,4-dione (HPD) chemotype. In biochemical assays

  人类免疫缺陷病毒（HIV）逆转录酶（RT）相关的核糖核酸酶H（RNase H）仍然是未经验证的药物靶标。据报道，HIV RNase H抑制剂通常缺乏显着的抗病毒活性。我们在此报告了3-羟基嘧啶-2,4-二酮（HPD）化学型的新的6-联苯甲基亚型的设计，合成，生化和抗病毒评估。在生化分析中，这种新亚型的类似物可在低纳摩尔范围内有效抑制RT RNase H，而在测试的最高浓度下却不会抑制RT聚合酶（pol）或整合酶链转移（INST）。在基于细胞的测定中，一些类似物在低微摩尔范围内抑制HIV，浓度高达100μM，却没有细胞毒性。
• Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed <i>Z</i>-Retentive Asymmetric Allylic Substitution Reaction
  作者：Lu Ding、Hao Song、Chao Zheng、Shu-Li You

  DOI：10.1021/jacs.2c01103

  日期：2022.3.23

  Medium-sized rings are important structural units, but their synthesis, especially in a highly enantioselective manner, has been a great challenge. Herein we report an enantioselective synthesis of medium-sized-ring lactones by an iridium-catalyzed Z-retentive asymmetric allylic substitution reaction. The reaction features mild conditions and a broad substrate scope. Various eight- to 11-membered-ring

  中等大小的环是重要的结构单元，但它们的合成，特别是以高度对映选择性的方式，一直是一个巨大的挑战。在这里，我们报告了通过铱催化的Z保持不对称烯丙基取代反应对中型环内酯的对映选择性合成。该反应条件温和，底物范围广。各种 8 至 11 元环内酯可以中等至优异的产率（高达 88%）和优异的对映选择性（高达 99% ee）提供。Z-烯丙基前体和 Ir 催化剂的利用对于中等环的形成至关重要。
• Discovery and structure–activity relationship of coumarin derivatives as TNF-α inhibitors
  作者：Jie-Fei Cheng、Mi Chen、David Wallace、Sovouthy Tith、Thomas Arrhenius、Hirotaka Kashiwagi、Yoshiyuki Ono、Akira Ishikawa、Haruhiko Sato、Toshiro Kozono、Hediki Sato、Alex M. Nadzan

  DOI：10.1016/j.bmcl.2004.03.022

  日期：2004.5

  The discovery and structure-activity relationship of a novel series of coumarin-based TNF-alpha inhibitors is described. Starting from the initial lead la, various derivatives were prepared surrounding the coumarin core structure to optimize the in vitro inhibitory activity of TNF-alpha production by human peripheral blood mononuclear cells (hPBMC), stimulated by bacterial lipopolysaccharide (LPS). Selected compounds also demonstrated in vivo inhibition of TNF-alpha production in rats. (C) 2004 Elsevier Ltd. All rights reserved.
• Nájera oxime-derived palladacycles catalyze intermolecular Heck reaction with Morita–Baylis–Hillman adducts. An improved and highly efficient synthesis of α-benzyl-β-ketoesters
  作者：Bruno R.V. Ferreira、Rodrigo V. Pirovani、Luis G. Souza-Filho、Fernando Coelho

  DOI：10.1016/j.tet.2009.06.084

  日期：2009.9

  An improved and highly efficient synthesis of several alpha-benzyl-beta-ketoesters from Morita-Baylis-Hillman adducts is described. These adducts were used as substrates for an intermolecular Heck reaction catalyzed by a Najera oxime-derived palladacycles. These efficient catalytic conditions probed to be very selective providing only the corresponding functionalized beta-ketoesters in high yield with no decarboxylation product. It seems that the method herein described is one of the most efficient for the synthesis of alpha-benzyl-beta-ketoesters. (C) 2009 Elsevier Ltd. All rights reserved.