2-methyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester | 88326-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-methyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester
• 英文别名: 2-vinyl-4-carbomethoxy-5-methyl-2,3-dihydrofuran；Methyl 2-methyl-5-vinyl-4,5-dihydro-3-furancarboxylate；methyl 2-ethenyl-5-methyl-2,3-dihydrofuran-4-carboxylate
• CAS: 88326-56-1
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: UYDXASYCPKOQOG-UHFFFAOYSA-N

物化性质

• 沸点：
  220.0±40.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-methyl 2-acetylhex-4-enoate 在 polymer-supported selenium bromide resin 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2-methyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Polymer-supported selenium-induced electrophilic cyclization: solid-phase synthesis of poly-substituted dihydrofurans and tetrahydrofurans

  摘要：

  Poly-substituted dihydrofurans and tetrahydrofurans have been synthesized through polymer-supported selenium-induced intramolecular electrophilic cyclization, followed by selenoxide syn-elimination or novel nucleophilic substitution cleavage of selenium resin with good yields and purities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.042

文献信息

• Alkyl substituted-2,3-dihydrofuran fragrance compositions
  申请人：National Distillers and Chemical Corporation

  公开号：US04681703A1

  公开（公告）日：1987-07-21

  Fragranced compositions and fragranced articles containing an aroma-augmenting or aroma-enhancing amount of a 2,3-dihydrofuran corresponding to the formula ##STR1## wherein R' is an alkyl group having from 1 to 4 carbon atoms, R** is an alkyl group having from 1 to 5 carbon atoms, R.sub.1 is an alkyl group having from 1 to 4 carbon atoms, R.sub.2 is hydrogen or an alkyl group having from 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen or a methyl group, and a process for obtaining same are provided.

  提供含有增强或增香量2,3-二氢呋喃的香料组合物和香料制品，其对应于以下式子：##STR1## 其中R'是具有1至4个碳原子的烷基，R**是具有1至5个碳原子的烷基，R.sub.1是具有1至4个碳原子的烷基，R.sub.2是氢或具有1至6个碳原子的烷基，而R.sub.3和R.sub.4是氢或甲基基团。还提供了一种获得它们的过程。
• 4-carbalkoxy-2-ethyl-2,3-dihydrofurans
  申请人：National Distillers and Chemical Corporation

  公开号：US04636571A1

  公开（公告）日：1987-01-13

  2,3-Dihydrofurans having highly desirable odor characteristics closely mimicking that of natural products are provided herein. The 2,3-dihydrofurans correspond to the formula ##STR1## wherein R' is an alkyl group having from 1 to 4 carbon atoms, R** is an alkyl group having from 1 to 5 carbon atoms, R.sub.1 is an alkyl group having from 1 to 4 carbon atoms, R.sub.2 is hydrogen or an alkyl group having from 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen or a methyl group. The 2,3-dihydrofuran compounds are useful in the preparation of fragrance compositions and fragranced articles and can be employed in conjunction with known fragrance materials to augment or enhance the aromas thereof.

  本文提供了具有高度理想气味特性，与天然产物非常相似的2,3-二氢呋喃。这些2,3-二氢呋喃对应于以下式子：##STR1## 其中R'是具有1至4个碳原子的烷基，R**是具有1至5个碳原子的烷基，R.sub.1是具有1至4个碳原子的烷基，R.sub.2是氢原子或具有1至6个碳原子的烷基，而R.sub.3和R.sub.4是氢原子或甲基基团。这些2,3-二氢呋喃化合物可用于制备香料组合物和带香气的物品，并可与已知香料材料一起使用以增强其香气。
• Dihydrofuran derivates useful as aroma chemicals, and process for their preparation
  申请人：QUANTUM CHEMICAL CORPORATION (a Virginia corp.)

  公开号：EP0128584A1

  公开（公告）日：1984-12-19

  2,4,5-trisubstituted-2,3-dihydrofurans useful as fragrance compounds are provided herein. The compounds of this invention correspond to the general formula wherein R is an ethyl or vinyl group, R2 is an alkyl group having from 1 to 4 carbon atoms and R1 is a hydrocarbon radical having from 3 to 10 carbon atoms. The 2,3-dihydrofuran compounds of the present invention are useful components in the preparation and formulation of fragranced cosmetic and toiletry products.

  本发明提供了可用作香料化合物的 2,4,5-三取代-2,3-二氢呋喃。 本发明的化合物符合通式，其中 R 是乙基或乙烯基，R2 是具有 1 至 4 个碳原子的烷基，R1 是具有 3 至 10 个碳原子的烃基。 本发明的 2,3-二氢呋喃化合物是制备和配制芳香化妆品和洗浴用品的有用成分。
• Barinelli, Lucio S.; Li, Zhong; Nicholas, Kenneth M., Organometallics, 1989, vol. 8, # 10, p. 2474 - 2476
  作者：Barinelli, Lucio S.、Li, Zhong、Nicholas, Kenneth M.

  DOI：——

  日期：——
• Optically Active Ruthenocenylbis(phosphines): New Efficient Chiral Phosphine Ligands for Catalytic Asymmetric Reactions
  作者：Tamio Hayashi、Akira Ohno、Shi-jie Lu、Yonetatsu Matsumoto、Emiko Fukuyo、Kazunori Yanagi

  DOI：10.1021/ja00089a011

  日期：1994.5

  New optically active ruthenocenylbis(phosphines) (R)-N,N-dimethyl-1-[(S)-1'2-bis(diphenylphosphino)-ruthenocenyl]propylamine [(R)-(S)-Et-BPPRA] (5a) and its ethylamine analog [(R)-(S)-BPPRA] (5b) were prepared by way of stereoselective lithiation of (R)-N,N-dimethyl-1-ruthenocenylalkylamines (4), which were obtained by the asymmetric ethylation or methylation (>96% ee) of ruthenocenecarboxaldehyde with the corresponding dialkylzincs in the presence of a catalytic amount of an optically active aminoalcohol 2 followed by stereoretentive amination of the resulting (R)-1-ruthenocenylalkanols (3). An X-ray diffraction study of the crystal structure of PdCl2[(R)-(S)-Et-BPPRA] (6a) revealed that the P-Pd-P bite angle of the ruthenocenylbis(phosphine) complex (100.47 degrees) is larger than that of the ferrocene analog and the phenyl rings on the phosphorus atoms are located closer to the chlorine ligand and palladium atom, suggesting that the ruthenocenylphosphines are more enantioselective chiral ligands for asymmetric reactions catalyzed by transition metal complexes. Actually, the ruthenocenylphosphines gave high enantioselectivity (higher than the ferrocene analog) in the palladium-catalyzed asymmetric silylation of allylic chlorides with 1,1-dichloro-1-phenyl-2,2,2-trimethyldisilane (PhCl(2)SiSiMe(3)) (up to 92% ee) and in the palladium-catalyzed cyclization of 2-butenylene dicarbonate with methyl acetylacetate forming a vinyldihydrofuran (up to 86% ee).