5-(3-Methyl-2-butenyl)-4-methyl-2(5H)-furanone | 66641-63-2

• 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: 5-(3-Methyl-2-butenyl)-4-methyl-2(5H)-furanone
• 英文别名: 3,7-dimethyl-2,6-octadien-4-olide；4-methyl-5-(3-methyl-2-butenyl)-2(5H)-furanone；3-methyl-2-(3-methylbut-2-enyl)-2H-furan-5-one
• CAS: 66641-63-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JIYJYONEZMWXLD-UHFFFAOYSA-N

物化性质

• 沸点：
  280.7±9.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3-Methyl-2-butenyl)-4-methyl-2(5H)-furanone 生成 4-甲基-5-(3'-甲基-2'-丁烯基)-二氢呋喃-2-酮
  参考文献：
  名称：

  YODA, HIDEMI;SHIRAKAWA, KOJI;TAKABE, KUNIHIKO, CHEM. LETT.,(1989) N, C. 1391-1392

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 potassium cyanide 、 重铬酸吡啶 、 18-冠醚-6 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 5-(3-Methyl-2-butenyl)-4-methyl-2(5H)-furanone
  参考文献：
  名称：

  A simple route to Δ2-butenolides from conjugated aldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(00)71458-4

文献信息

• SYNTHESES OF PERILLENE AND ROSEFURAN FROM COMMON STARTING MATERIALS
  作者：Seiichi Takano、Masamichi Morimoto、Shigeki Satoh、Kunio Ogasawara

  DOI：10.1246/cl.1984.1261

  日期：1984.7.5

  Two structurally isomeric furanomonoterpenes perillene and rosefuran have been synthesized using methallyl alcohol and prenyl chloride as common starting materials.

  使用甲烯丙醇和异戊二烯氯作为常见的起始原料，合成了两种结构异构的呋喃单萜紫杉烯和蔷薇呋喃。
• Method for producing rosefuran precursor and intermediates therefor
  申请人：Toyotama Perfumery Co., Ltd.

  公开号：US05627288A1

  公开（公告）日：1997-05-06

  Disclosed are 3,7-dimethyl-4-oxo-7-octenoic acid and its alkyl esters which are intermediates for producing a fragrance, rosefuran and which are represented by: ##STR1## where R is H or a lower alkyl. The compounds [1] are obtained by reacting 2-methyl-3-alkoxycarbonylpropionic acid halide and 3-methyl-3-butenylmagnesium halide. The octenoic acid [1] is treated with acetic anhydride under heat in the presence of an acidic catalyst to give 3,7-dimethyl-2,6-octadien-4-olide. The olide is reduced in an ordinary manner to give rosefuran.

  揭示了3,7-二甲基-4-氧代-7-辛烯酸及其烷基酯，它们是生产香精玫瑰呋喃的中间体，并且表示为：##STR1##其中R为H或较低的烷基。化合物[1]通过反应2-甲基-3-烷氧羰基丙酸卤和3-甲基-3-丁烯基镁卤得到。辛烯酸[1]在酸性催化剂存在下在热条件下与乙酸酐反应，生成3,7-二甲基-2,6-辛二烯-4-酮。这种酮类化合物通常通过还原方法还原成玫瑰呋喃。
• Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids
  作者：Pedro Bonete、Carmen Najera

  DOI：10.1021/jo00090a043

  日期：1994.6

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).
• Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1989, p. 1391 - 1392
  作者：Yoda, Hidemi、Shirakawa, Koji、Takabe, Kunihiko

  DOI：——

  日期：——
• COREY E. J.; SCHMIDT G., TETRAHEDRON LETT., 1980, 21, NO 8, 731-734
  作者：COREY E. J.、 SCHMIDT G.

  DOI：——

  日期：——