ethyl 2,2,6-trimethyl-4-oxo-2,3-dihydro-4H-pyran-5-carboxylate | 18782-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 2,2,6-trimethyl-4-oxo-2,3-dihydro-4H-pyran-5-carboxylate
• 英文别名: 5-carbethoxy-2,2,6-trimethyl-2,3-dihydro-4H-pyran-4-one；2,6,6-trimethyl-4-oxo-5,6-dihydro-4H-pyran-3-carboxylic acid ethyl ester；2,6,6-trimethyl-4-oxo-5H-pyran-3-carboxylic acid ethyl ester；ethyl 2,2,6-trimethyl-4-oxo-3H-pyran-5-carboxylate
• CAS: 18782-59-7
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: BFLKLYXPEIASDA-UHFFFAOYSA-N

物化性质

• 沸点：
  275.2±29.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,2,6-trimethyl-4-oxo-2,3-dihydro-4H-pyran-5-carboxylate 在 sodium hydroxide 作用下， 生成 ethyl 5-methyl-3-oxo-4-hexenoate
  参考文献：
  名称：

  Gelin,S.; Gelin,R., Bulletin de la Societe Chimique de France, 1969, p. 4091 - 4102

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 5-methyl-3-(2-methylprop-1-enyl)-1,2-oxazole-4-carboxylate 在 水 、 molybdenum hexacarbonyl 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到ethyl 2,2,6-trimethyl-4-oxo-2,3-dihydro-4H-pyran-5-carboxylate
  参考文献：
  名称：

  Jones, Raymond C. F.; Bhalay, Gurdip; Carter, Paul A., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1715 - 1716

  摘要：

  DOI：

文献信息

• Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: the first three step total synthesis of the dihydronaphthopyran-4-one class of natural products
  作者：Andivelu Ilangovan、Palaniappan Sakthivel

  DOI：10.1039/c4ra11174e

  日期：——

  Intermolecular domino C-acylation/6π-oxaelectrocyclization between β-ketoesters and α,β-unsaturated acid chlorides took place readily in the presence of CaCl2 to afford a variety of polysubstituted 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones, in good yields. The products were successfully exploited as precursors, for a simple and efficient construction of a naphthalene fused pyran-4-one ring system.

  在CaCl 2的存在下，β-酮酸酯与α，β-不饱和酰氯之间的分子间多米诺C-酰化/6π-氧杂电环化反应很容易发生，从而提供了多种多取代的5-carboalkoxy-2,3-dihydro-4 H -pyran -4-ones，良率高。该产品已成功地用作前体，用于萘稠合的吡喃-4-酮环系统的简单有效构建。这种分子内Friedel-Crafts酰基化芳构化方法可用于合成抑制植物生长的二氢萘吡喃酮类天然产物。
• A novel synthetic method of dihydro-4-pyrone derivatives and its application to the syntheses of ar-atlantone and (±)-ar-turmerone
  作者：Takashi Sakai、Kazuyoshi Miyata、Mutsumi Ishikawa、Akira Takeda

  DOI：10.1016/s0040-4039(00)94935-9

  日期：1985.1

  Reaction of 1,3-dihalo-3-methy]-2-butanone with t-butyl acetoacetate (NaH) gave t-butyl 3,4-dihydro-2,2,6-trimethyl-4-oxo-2H-pyran-5-carboxylate via the Favorskii-type rearrangement. Michael addition of 4-methylphenyllithium (CuI) followed by ring cleavage with Me3 SiCl-NaI in DMF or PrCN afforded ar-atlantone as well as (±)-ar-turmerone selectively.

  1,3-二卤-3-甲基] -2-丁酮与乙酰乙酸叔丁酯（NaH）反应生成叔丁基3,4-二氢-2,2,6-三甲基-4-氧代-2H-吡喃-通过Favorskii型重排生成5-羧酸盐。迈克尔加成4- methylphenyllithium（CUI）的随后用我环切割3在DMF或PRCN得到的SiCl-的NaI AR -atlantone以及（±） -芳-turmerone选择性。
• Discovery of 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-ones as a new class of pathogen specific anti-leptospiral agents
  作者：Andivelu Ilangovan、Palaniappan Sakthivel、Karikalacholan Sivasankari、Charles Solomon Akino Mercy、Kalimuthusamy Natarajaseenivasan

  DOI：10.1016/j.ejmech.2016.09.020

  日期：2017.1

  A simple and efficient method for the synthesis of a series of 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-one derivatives starting from 5-carboalkoxy-2,3-dihydropyranone (5-CDHPs) has been developed. Pyranoisoxazolones 10a-j, dihydronaphthopyran-4-one (DHNPs) class of natural product 12b and 12c and its analogues 12a and 13a-c were preliminarily screened against pathogenic leptospiral serovar Autumnalis strain N2 at various concentrations. Six pyranoisoxazolones, 10b, 10d, 10f, 10g, 10i and 10j which displayed very good anti-leptospiral activity was taken for secondary screening against twelve strains of pathogenic and one non-pathogenic leptospiral serovars. While all the compounds displayed significant anti-leptospiral activity against the pathogenic serovars at MIC of 62.5-500 mu g/mL. Compounds 10d, 10g and 10j did not show any significant effect on non-pathogenic serovar. Inhibition of leptospires at a significant level by pyranoisoxazolone 10g was confirmed using RT-qPCR assay. In vivo treatment of BALB/c mice with compound 10g revealed that, it has 95% survivability against the pathogenic strain Canicola and also showed inhibition of renal colonization of leptospires. Compound 10g was found to show cytotoxicity against THP-1 cells only at higher concentration (>= 75 mu g/mL). Effective binding of compound 10g with leptospiral outer membrane protein LipL32 observed via in silico molecular docking provided a suitable explanation for pathogen specificity of compound 10g. Antibiotics acting against leptospirosis in human are very few. The results obtained from in vitro, in vivo and in silico study reveals that 6,7-dihydro-3H-pyrano[4,3-c]isoxazol-3-ones class of compounds are lead molecules for further development as pathogen specific anti-leptospiral agents. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Organocuprate conjugate addition to 2,3-dihydro-4H-pyran-4-ones
  作者：Daniel L. Boring、Robert D. Sindelar

  DOI：10.1021/jo00250a042

  日期：1988.7
• CHANTEGREL, B.;NADI, ABDEL, ILAH;GELIN, S., HETEROCYCLES, 1984, 22, N 2, 365-369
  作者：CHANTEGREL, B.、NADI, ABDEL, ILAH、GELIN, S.

  DOI：——

  日期：——