2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester | 38453-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(tert-butyl)-2-methylfuran-3-carboxylate；ethyl 2-methyl-5-tert-butylfuran-3-carboxylate；ethyl 5-tert-butyl-2-methylfuran-3-carboxylate；Ethyl 5-tert-butyl-2-methyl-3-furoate；5-tert-butyl-2-methyl-furan-3-carboxylic acid ethyl ester；5-tert-Butyl-2-methyl-furan-3-carbonsaeure-aethylester
• CAS: 38453-94-0
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: MDULATFBKVEEQN-UHFFFAOYSA-N

物化性质

• 沸点：
  80-81 °C(Press: 2 Torr)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83.9%的产率得到5-叔丁基-2-甲基呋喃-3-羧酸
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

  摘要：

  All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities.All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 mu M (compared to liarozole (IC50 = 2.45 mu M) and S8 (IC50 = 3.21 mu M)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of beta-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.036
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 生成 2-methyl-5-(tert-butyl)furan-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  N-溴代琥珀酰亚胺作为氧化剂，通过多米诺酸-酸催化脂肪醛和1,3-二羰基化合物的自动串联催化诱导的三取代基呋喃的合成

  摘要：

  使用N-溴代琥珀酰亚胺（NBS）作为氧化剂，开发了一种简单的氯化铝（III）催化的脂肪族醛和1,3-二羰基化合物合成三取代呋喃的方法。该方法对于合成各种呋喃衍生物是有效的。使用先前报告的方法无法访问某些产品。从机械上讲，该反应涉及一种基于新报道的酸-酸催化串联反应的自动串联催化，以确保呋喃得以成功合成。

  DOI：

  10.1002/adsc.201700074

文献信息

• Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: a direct synthesis of trisubstituted furans
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2014.07.086

  日期：2014.9

  method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to wide substrate scope. Moreover, this synthesis employs cheap Cu(MeCN)4PF6 as the catalyst and no additional ligand is needed. Similar reaction has also been

  基于Cu（I）催化的末端炔烃与β-酮α-重氮酸酯的反应，已经开发了一种三取代呋喃的合成方法。该合成2,3,5-三取代呋喃的方法操作简单，适用于广泛的底物范围。此外，该合成采用廉价的Cu（MeCN）4 PF 6作为催化剂，不需要其他配体。类似的反应也已用于（E）-2-重氮-3-（甲氧基亚氨基）丁酸乙酯，用于合成2,3,5-三取代的N-甲氧基吡咯，但效果有限。
• One-Pot Synthesis of Furans Using Base- and Acid-Supported Reagents ‘Na2CO3/Al2O3-PPA/SiO2'
  作者：Tadashi Aoyama、Takashi Nagaoka、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-0030-1258402

  日期：2011.2

  convenient method for the one-pot synthesis of furans from β-keto esters and α-halo ketones was developed using an acid- and base-supported reagent system ‘Na2CO3/Al2O3-PPA/SiO2’. The condensation reaction of triketones, which are formed from the reaction of β-keto esters with α-halo ketones in the presence of Na2CO3/Al2O3, was promoted by PPA/SiO2 to give the corresponding furans in good yields. This method

  开发了一种方便的方法，可使用酸和碱支持的试剂系统'Na 2 CO 3 / Al 2 O 3 -PPA / SiO 2 '从β-酮酯和α-卤代酮一锅合成呋喃。PPA / SiO 2促进了β-酮酸酯与α-卤代酮在Na 2 CO 3 / Al 2 O 3存在下的反应而形成的三酮缩合反应，得到了相应的呋喃。产量。与分步法相比，该方法简单易行，收率好。 呋喃-一锅合成-支持的试剂
• 2,3,4- or 2,3,5-Trisubstituted Furans:  Catalyst-Controlled Highly Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl Ketones
  作者：Shengming Ma、Junliang Zhang

  DOI：10.1021/ja036616g

  日期：2003.10.1

  furans were highly regioselectively formed from the cycloisomerization reaction of the same starting cyclopropenes 1 via the subtle choice of the transition metal halides. Under the catalysis of 5 mol % PdCl2(CH3CN)2, 2,3,5-trisubstituted furans 2 were given in 50-88% yields with 95-99% regioselectivities, while 2,3,4-trisubstituted furans 3 were formed in 78-96% yields with 99% regioselectivities under

  2,3,4- 或 2,3,5- 三取代呋喃通过过渡金属卤化物的微妙选择，由相同起始环丙烯 1 的环异构化反应高度区域选择性地形成。在 5 mol% PdCl2(CH3CN)2 的催化下，2,3,5-三取代呋喃 2 的产率为 50-88%，区域选择性为 95-99%，而 2,3,4-三取代呋喃 3 则在在 5 mol% CuI 的催化下，78-96% 的产率和 99% 的区域选择性。
• HETEROCYCLIC COMPOUND
  申请人：Banno Yoshihiro

  公开号：US20100256156A1

  公开（公告）日：2010-10-07

  The present invention provides a heterocyclic compound represented by the following formula (I), which has a glucagon antagonistic action and is useful for the prophylaxis or treatment of diabetes and the like, a compound represented by wherein ring A is an optionally substituted benzene ring and the like; Y is a nitrogen atom and the like; X is —O— and the like; R 4 is a hydrogen atom and the like; R 5 and R 6 are each independently a hydrogen atom and the like; R 1 is an optionally substituted hydrocarbon group and the like; R 2 is a hydrogen atom and the like; and R 3 is —(CH 2 ) 3 —COOH and the like, or a salt thereof.

  本发明提供了一种由以下式（I）表示的杂环化合物，该化合物具有葡萄糖高升素拮抗作用，并可用于预防或治疗糖尿病等疾病，其中，式中环A为可选取代苯环等；Y为氮原子等；X为—O—等；R4为氢原子等；R5和R6各自独立地为氢原子等；R1为可选取代的碳氢基团等；R2为氢原子等；R3为—（CH2）3—COOH等，或其盐。
• Effects of 5-tert-Butyl and 5-Methyl Group Substitution on the Reactivity and Dimerization Products of Furan-Based o-Quinodimethanes
  作者：Walter S. Trahanovsky、Chin-Hsing Chou、Timothy J. Cassady

  DOI：10.1021/jo00088a054

  日期：1994.5