乙基4-环己基-4-氧代丁酸酯 | 54966-52-8

• 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
• 中文名称: 乙基4-环己基-4-氧代丁酸酯
• 英文名称: ethyl 4-cyclohexyl-4-oxobutanoate
• CAS: 54966-52-8
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: FCERNGANVYWSDA-UHFFFAOYSA-N

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：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  乙基4-环己基-4-氧代丁酸酯 在 sodium hydroxide 作用下， 反应 12.0h， 生成 4-环己基-4-氧代丁酸
  参考文献：
  名称：

  4-(trans-4-Methylcyclohexyl)-4-Oxobutyric Acid (JTT-608). A New Class of Antidiabetic Agent

  摘要：

  During an investigation of drugs for improving the beta-cell response to glucose, we found that 4-cyclohexyl-4-oxobutyric acid selectively improved glucose-stimulated insulin release and glucose tolerance in both normal and diabetic rats. A series of 4-cycloalkyl-4-oxobutyric acids and related compounds were synthesized and evaluated for their effects on the glucose tolerance test and fasting euglycemia. This study elucidated the structural requirements for drug activity and determined th at the optimum compound was 4-(trans-4-methylcyclohexyl)-4-oxobutyric acid 7 (JTT-608). This compound improved glucose tolerance from an oral dose of 3 mg/kg and did not change fasting euglycemia even at an oral dose of 30 mg/kg. Selective improvement of glucose-induced insulin secretion was observed in studies using neonatal streptozotocin rats (nSTZ rats) and perfused pancreases isolated from nSTZ rats.

  DOI：

  10.1021/jm9804228
• 作为产物：
  描述：

  ethyl 4-cyclohexyl-4-phenylsulfanylbut-3-enoate 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以79%的产率得到乙基4-环己基-4-氧代丁酸酯
  参考文献：
  名称：

  1,4-和1,4,7-多羰基化合物的新策略

  摘要：

  Synthese de composes dicarbonyles-1,4 par 反应 de Wittig sur des aldehydes, la methode peut etre etendue a la synthese de composes tricarbonyles-1,4,7

  DOI：

  10.1021/ja00223a060

文献信息

• Synthesis of γ-, δ-, and ε-Lactams by Asymmetric Transfer Hydrogenation of <i>N</i>-(<i>tert</i>-Butylsulfinyl)iminoesters
  作者：David Guijarro、Óscar Pablo、Miguel Yus

  DOI：10.1021/jo400164y

  日期：2013.4.19

  Highly enantiomerically enriched γ- and δ-lactams have been prepared by a simple and very efficient procedure that involves the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters followed by desulfinylation of the nitrogen atom and spontaneous cyclization to the desired lactams during the basic workup procedure. Five- and six-membered ring lactams bearing aromatic, heteroaromatic

  高度对映体富集的γ-和δ-内酰胺是通过一种简单且非常有效的方法制备的，该方法包括N-（叔丁基亚磺酰基）亚氨基酸酯的不对称转移氢化，接着是氮原子的脱亚磺酰化，并在反应过程中自发环化为所需的内酰胺​​。基本的检查程序。已经以非常高的产率获得了带有芳族，杂芳族和脂族取代基的五元和六元环内酰胺，并且ee高达99％以上。稍加修改，即可制备出高收率和极高对映选择性的ε-内酰胺。通过改变亚磺酰基手性助剂的绝对构型，可以以相等的效率制备最终内酰胺的两种对映体。
• Direct Aldehyde Csp² −H Functionalization through Visible-Light-Mediated Photoredox Catalysis
  作者：Minh Duy Vu、Mrinmoy Das、Xue-Wei Liu

  DOI：10.1002/chem.201704224

  日期：2017.11.13

  challenge for synthetic chemists. In recent years there has been considerable interest in using selective C−H activation as a direct route for generating reactive intermediates. Herein, the use of visible‐light‐mediated dual photoredox organocatalysis as a mild and effective method for C −H activation of aldehydes is reported, resulting in the generation of acyl radicals. These nucleophilic acyl radical

  在良性条件下形成碳-碳键的方法的开发对于合成化学家来说是一个持续的挑战。近年来，使用选择性CH活化作为产生反应性中间体的直接途径引起了极大的兴趣。在此， 据报道使用可见光介导的双光氧化还原有机催化作为温和有效的醛CH活化方法，从而导致了酰基自由基的产生。这些亲核酰基基团可以通过亲电子烯烃或镍催化的交叉偶联反应进行加成，以快速获得广泛的不对称酮，在许多有机结构单元中都发现了这种不对称酮。
• From a Designer Drug to the Discovery of Selective Cannabinoid Type 2 Receptor Agonists with Favorable Pharmacokinetic Profiles for the Treatment of Systemic Sclerosis
  作者：Bei-Er Jiang、Xingwu Jiang、Qiansen Zhang、Qiuwen Liang、Zi-Liang Qiu、Xiang-Bai Sun、Jun-Jie Yang、Si Chen、Chunyang Yi、Xiaolei Chai、Mingyao Liu、Li-Fang Yu、Weiqiang Lu、Han-Kun Zhang

  DOI：10.1021/acs.jmedchem.0c01023

  日期：2021.1.14

  discover novel and selective CB2 receptor agonists, 1 was selected as a starting point for hit molecule identification and a class of 1H-pyrazole-3-carboxamide derivatives were thus designed, synthesized, and biologically evaluated. Systematic structure–activity relationship investigations resulted in the identification of the most promising compound 66 as a selective CB2 receptor agonist with favorable pharmacokinetic

  合成大麻素，如例示的SDB-001（1），结合两者CB1和CB2受体并发挥类似于大麻素样作用（ - ） -反式-Δ 9四氢大麻酚，精神组分存在于大麻植物的主要。由于发现CB1受体配体具有严重的精神病学副作用，因此越来越多的注意力转向开发CB2受体的潜在治疗价值。在我们发现新颖和选择性CB2受体激动剂的努力中，选择1作为命中分子鉴定的起点，并选择1 H因此，设计，合成了对-吡唑-3-羧酰胺衍生物，并对其进行了生物学评估。通过系统的结构-活性关系研究确定了最有前途的化合物66，它是具有良好药代动力学特征的选择性CB2受体激动剂。特别是，在博来霉素诱导的系统性硬化小鼠模型中，66种治疗显着减轻了真皮炎症和纤维化，支持CB2受体激动剂可能作为治疗系统性硬化的潜在疗法。
• One-Pot Synthesis of Oxo Acid Derivatives by RhI-Catalyzed Chelation-Assisted Hydroacylation
  作者：Eun-Ae Jo、Chul-Ho Jun

  DOI：10.1002/ejoc.200600236

  日期：2006.6

  Various oxo acid derivatives were obtained directly from the reaction of aliphatic and aromatic aldehydes with ω-alkenoic acid derivatives in the presence of rhodium(I) complexes and 2-amino-3-picoline. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  在铑（I）配合物和2-氨基-3-甲基吡啶的存在下，通过脂肪族和芳香族醛与ω-链烯酸衍生物的反应直接获得各种含氧酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Process for producing and purifying 3,4-dihydrocoumarin
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0492940A1

  公开（公告）日：1992-07-01

  A 3-(2-cyclohexanoyl)propionic acid ester is in the presence of a solid metallic catalyst, cyclized and dehydrogenised at 100° to 350°C, optionally with solvent and promotor to given 3,4-dihydrocoumarin [D] in 30-70 mol% yield and coumarin [C] 5-35 mol% and by-product dihydrocinnamic acid [A], 0.1-20 wt%; hydrogenation can convert [C] to [D]. The reaction mixture is purified by (i) to remove acidic compounds washing with an aqueous solution of an alkali (e.g., NaOH or NAHCO₃); if a strong alkali metal or alkaline earth hydroxide is used its amount is not more than 1.5 equivalent per equivalent of [D]; the amount of solution is 0.1 to 10 times by weight that of the reaction mixture. The washing reduces the content of [A] to 1% by weight of the weight of [D], and/or (ii) to remove high boiling o-ethylphenyl cyclohexylpropionate/dihydrocinnamate to 2% by weight of that of [D] distillation at a reflux ratio of not more than 5 or in a tower having 10 stages or less, at 13-13330 Pa (0.1 to 10 Torr); (i) and (ii) can be used together in either order, followed by rectification in a 5-100 stage tower at a reflux ratio of 1 to 50, to recover [D]. The product contains not more than 0.05% of [A] and is suitable for use in perfume.

  3-(2-环己酰基)丙酸酯在固体金属催化剂存在下，于 100°至 350°C 环化和脱氢，可选择使用溶剂和促进剂，得到 3,4-二氢香豆素[D]，产率 30-70 mol%，香豆素[C]5-35 mol%，副产物二氢肉桂酸[A]0.1-20 wt%；氢化可将[C]转化为[D]。 反应混合物通过以下方法纯化：(i) 用碱（如 NaOH 或 NAHCO₃）水溶液洗涤以去除酸性化合物；如果使用强碱金属或碱土氢氧化物，其用量不超过每当量[D]1.5 个当量；溶液量为反应混合物重量的 0.1 至 10 倍。洗涤使[A]的含量降低到[D]重量的 1%，和/或(ii)除去高沸点邻乙基苯基环己基丙酸酯/二氢肉桂酸酯，使其含量降低到[D]重量的 2%。1至10托）；(i)和(ii)可按任一顺序同时使用，然后在回流比为1至50的5至100级塔中进行精馏，以回收[D]。 产品中的[A]含量不超过 0.05%，适合用于香水。