ethyl 2-oxo-5-phenylcyclohexanecarboxylate | 13658-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-oxo-5-phenylcyclohexanecarboxylate
• 英文别名: ethyl 4-phenylcyclohexanone-2-carboxylate；Ethyl 2-oxo-5-phenylcyclohexane carboxylate；α-Aethoxycarbonyl-γ-phenyl-cyclohexanon；2-Oxo-5-phenylcyclohexancarboxylat；Ethyl 2-oxo-5-phenylcyclohexane-1-carboxylate
• CAS: 13658-19-0
• 化学式: C₁₅H₁₈O₃
• mdl: MFCD16517135
• 分子量: 246.306
• InChiKey: JZNYKTFYDHOKCD-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 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-oxo-5-phenylcyclohexanecarboxylate 在 氨 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 C₂₀H₁₈ClN₃O
  参考文献：
  名称：

  Discovery of bicyclic pyrazoles as class III histone deacetylase SIRT1 and SIRT2 inhibitors

  摘要：

  A series of bicyclic pyrazole carboxamides was synthesized and tested for inhibitory activity against the class III deacetylase sirtuin enzymes. Moderate to low micromolar inhibitory activities were obtained against SIRT1 and SIRT2. These bicyclic pyrazole compounds represent a new class of sirtuin inhibitors with a preference for SIRT1 over SIRT2. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.068
• 作为产物：
  描述：

  4-苯基环己酮 、 碳酸二乙酯 在 potassium hydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-oxo-5-phenylcyclohexanecarboxylate
  参考文献：
  名称：

  Discovery of bicyclic pyrazoles as class III histone deacetylase SIRT1 and SIRT2 inhibitors

  摘要：

  A series of bicyclic pyrazole carboxamides was synthesized and tested for inhibitory activity against the class III deacetylase sirtuin enzymes. Moderate to low micromolar inhibitory activities were obtained against SIRT1 and SIRT2. These bicyclic pyrazole compounds represent a new class of sirtuin inhibitors with a preference for SIRT1 over SIRT2. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.068

文献信息

• New Strategies for the Efficient Synthesis of Medium-Sized Bicyclic γ-Alkylidenebutenolides Based on Regioselective Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with Oxalyl Chloride
  作者：Peter Langer、Tobias Eckardt、Nehad N. R. Saleh、Inass Karimé、Peter Müller

  DOI：10.1002/1099-0690(200110)2001:19<3657::aid-ejoc3657>3.0.co;2-5

  日期：2001.10

  efficiently prepared by Me3SiOTf-catalyzed cyclization of cyclic bis(silyl enol ethers) with oxalyl chloride. In addition, a new strategy for the synthesis of medium-sized bicyclic hybrids of butenolides and medium-sized cyclic ethers − based on sequential [3+2] cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, Mitsunobu reaction, and ring-closing metathesis − is reported.

  通过 Me3SiOTf 催化环状双（甲硅烷基烯醇醚）与草酰氯的环化反应，有效地制备了中等大小的双环 γ-亚烷基丁烯内酯。此外，合成中型丁烯内酯和中型环醚的双环杂化物的新策略 - 基于 1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯的顺序 [3+2] 环化，Mitsunobu反应和闭环复分解 - 报道。
• Cycloalkene derivatives, process for producing the same, and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06495604B1

  公开（公告）日：2002-12-17

  The present invention provides a compound represented by the formula: wherein R represents an aliphatic hydrocarbon group optionally having substituents, an aromatic hydrocarbon group optionally having substituents, a heterocyclic group optionally having substituents, a group represented by the formula: OR1 (wherein R1 represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents) or a group represented by the formula: wherein R1b represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R1c is, same with or different from R1b, a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R0 represents a hydrogen atom or an aliphatic hydrocarbon group, or R and R0 represents a bond with each other, Ar represents an aromatic hydrocarbon group optionally having substituents, and n is an integer of 1 to 4, or a salt thereof, which is a agent for preventing or treating diseases such as cardiac disease, autoimmune disease, septick shock, etc.

  本发明提供了一种由以下公式表示的化合物：其中R代表一个具有取代基的脂肪烃基、一个具有取代基的芳香烃基、一个具有取代基的杂环基、一个由公式表示的基团：OR1（其中R1代表氢原子或具有取代基的脂肪烃基）或一个由公式表示的基团：其中R1b代表氢原子或具有取代基的脂肪烃基，R1c与R1b相同或不同，代表氢原子或具有取代基的脂肪烃基，R0代表氢原子或脂肪烃基，或者R和R0彼此之间形成键结合，Ar代表具有取代基的芳香烃基，n为1至4的整数，或其盐，用作预防或治疗心脏病、自身免疫疾病、感染性休克等疾病的药物。
• An expedient, stereoselective synthesis of highly functionalized cyclic compounds
  作者：Ewa Krawczyk、Krzysztof Owsianik、Aleksandra Skowrońska、Michał Wieczorek、Wiesław Majzner

  DOI：10.1039/b207700k

  日期：——

  New thiophosphates containing functionalized cyclic ketone derivatives as ligands have been stereoselectively prepared from readily available starting materials. Full axial stereoselectivity of the NaBH4 reduction of the carbonyl group in thiophosphates providing the corresponding thiols or sulfides has been demonstrated. The sulfides have been transformed into new functionalized cyclic Baylis–Hillman type adducts of defined configuration. The prospects for the useful synthetic application of these adducts appear to be very promising.

  含有官能化环酮衍生物作为配体的新硫磷酸酯已从易得的起始材料中立体选择性地合成。已经证明，NaBH4对硫磷酸酯中羰基的还原反应具有完全的轴向立体选择性，生成相应的硫醇或硫化物。这些硫化物已被转化为具有明确定型的新型官能化环状Baylis–Hillman型加合物。这些加合物在有用合成应用方面的前景看起来非常可观。
• Efficient and Stereoselective Synthesis of Bicyclo[3.2.1]octan-8-ones: Synthesis and Palladium-Catalyzed Isomerization of Functionalized 2-Vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans
  作者：Peter Langer、Edith Holtz、Nehad N. R. Saleh

  DOI：10.1002/1521-3765(20020215)8:4<917::aid-chem917>3.0.co;2-1

  日期：2002.2.15

  diastereoselective formation of 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans. The products could be efficiently transformed into functionalized bicyclo[3.2.1]octan-8-ones by a palladium-catalyzed rearrangement reaction. In case of sulfone derivatives, this rearrangement proceeds with high stereospecifity to give exclusively the endo-configured diastereomers. The bicyclo[3.2.1]octane skeleton is present

  据报道，用1,4-二溴-2-丁烯将二锂化的环状β-酮酯和β-酮砜进行新的C，O-环二烷基化反应会导致区域选择性和非对映选择性形成2-乙烯基-2,3,3a， 4,5,6-六氢-2,3-苯并呋喃。该产物可以通过钯催化的重排反应有效地转化为官能化的双环[3.2.1] octan-8-one。在砜衍生物的情况下，该重排以高立体特异性进行，以仅给出内构型的非对映异构体。双环[3.2.1]辛烷骨架存在于许多重要的药理天然产物中。
• Regio- and Stereoselective Synthesis ofNor-Nonactinic Acid Derivatives—Kinetic Reaction Control in the Lewis Acid Mediated Domino Reaction of 1,3-Dicarbonyl Dianions with 1-Bromo-2,3-epoxypropanes
  作者：Peter Langer、Ilia Freifeld

  DOI：10.1002/1521-3765(20010202)7:3<565::aid-chem565>3.0.co;2-e

  日期：2001.2.2

  Reaction of 1,3-dicarbonyl dianions with epibromohydrin derivatives results in formation of functionalized 2-alkylidene-5-hydroxymethyltetrahydrofurans. These reactions proceed by chemoselective attack of the dianion onto the carbon attached to the bromine atom and subsequent nucleophilic attack of the resultant monoanion onto the epoxide. The cyclization products, which were formed with very good

  1，3-二羰基二价阴离子与表溴醇衍生物的反应导致形成官能化的2-亚烷基-5-羟甲基四氢呋喃。这些反应通过将二价阴离子化学选择性地攻击到与溴原子相连的碳上，然后将所生成的单阴离子随后的亲核攻击到环氧化物上。具有很好的区域选择性和立体选择性形成的环化产物具有药理学意义，并代表了合成天然产物的通用结构单元。