methyl 2-bromo-5-formylfuran-4-carboxylate | 1006598-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 2-bromo-5-formylfuran-4-carboxylate
• 英文别名: methyl 5-bromo-2-formyl-furan-3-carboxylate；Methyl 5-bromo-2-formylfuran-3-carboxylate；methyl 5-bromo-2-formylfuran-3-carboxylate
• CAS: 1006598-64-6
• 化学式: C₇H₅BrO₄
• 分子量: 233.018
• InChiKey: FQKUUDQFLSMYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-5-formylfuran-4-carboxylate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 sodium chlorite 、 potassium phosphate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 palladium diacetate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 25.0h， 生成 methyl 2-(phenylcarbamoyl)-5-pyrazolo[1,5-a]pyridin-5-yl-furan-3-carboxylate
  参考文献：
  名称：

  WO2020173739A5

  摘要：

  公开号：

  WO2020173739A5
• 作为产物：
  描述：

  methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate 在 吡啶 、 水 作用下， 反应 1.33h， 以87%的产率得到methyl 2-bromo-5-formylfuran-4-carboxylate
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.030

文献信息

• TiCl4-mediated olefination of aldehydes with acetic acid and alkyl acetates: a stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters
  作者：John Kallikat Augustine、Chandrakantha Boodappa、Srinivasa Venkatachaliah、Ayyampillai Mariappan

  DOI：10.1016/j.tetlet.2014.04.098

  日期：2014.6

  the preparation of α,β-unsaturated carboxylic acids and corresponding esters with (E)-stereoselectivity via the TiCl4-mediated olefination of aldehydes. The method, which uses readily available acetic acid or its alkyl esters as active methylene partners, is more flexible and complementary to conventional routes in the preparation of (E)-cinnamic acid derivatives.

  已经开发了一种新的方法，用于通过TiCl 4介导的醛的烯化反应制备具有（E）-立体选择性的α，β-不饱和羧酸和相应的酯。该方法使用现成的乙酸或其烷基酯作为活性亚甲基伴侣，在制备（E）-肉桂酸衍生物时，它比常规方法更具灵活性和互补性。
• Total synthesis of (+)-Z-deoxypukalide, a furanobutenolide-based cembranoid isolated from the pacific octocoral Leptogorgia spp.
  作者：Bencan Tang、Christopher D. Bray、Gerald Pattenden、Joseph Rogers

  DOI：10.1016/j.tet.2010.01.059

  日期：2010.3

  A total synthesis of (+)-Z-deoxypukalide 3 using a combination of Stille and Nozaki-Hiyama-Kishi(NHK) coupling reactions as key steps, is described. During this study a new practical synthesis of the substituted butenolide intermediate 10, based on a combination of RCM and CM reactions from the cyclobutene ester 21 in the presence of 2-methylpropenol was also developed. Attempts to apply the intramolecular NHK reaction to the substrates 8a and 8b containing an ester group adjacent to the reacting aldehyde functionality gave disappointing low yields (<6%) of the corresponding coupled products 9. The synthetic (+)-Z-deoxypukalide 3 was correlated with naturally derived material, and also with pukalide 1, the first member of the furanobutenolide-based cembranoids to be isolated from corals. (C) 2010 Elsevier Ltd. All rights reserved.
• PYRAZOLOPYRIDINE DERIVATIVES AS INHIBITORS OF PASK
  申请人：Galapagos NV

  公开号：US20220144823A1

  公开（公告）日：2022-05-12

  The present invention discloses compounds according to Formula I: wherein R 1 , R 2 , R 3a , R 3b , Het, X and the subscript n are as defined herein. The present invention relates to compounds, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of endocrine, nutritional, metabolic, and/or cardiovascular diseases by administering the compound of the invention.
• WO2020173739A5
  申请人：——

  公开号：WO2020173739A5

  公开（公告）日：2023-02-20
• A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes
  作者：John Kallikat Augustine、Y. Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1016/j.tet.2007.11.030

  日期：2008.1

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.