3,4-dimethyl-1-heptylfuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,4-dimethyl-1-heptylfuran
• 英文别名: 3,4-dimethyl-2-n-heptylfuran；2-Heptyl-3,4-dimethylfuran
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: HHLJRVHFJNFYSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-3-甲基戊-2-烯-4-炔-1-醇 在 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 草酰氯 、 copper(I) bromide dimethylsulfide complex 、 18-冠醚-6 、 potassium tert-butylate 、 水 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 3,4-dimethyl-1-heptylfuran
  参考文献：
  名称：

  Synthesis of furans by base-catalyzed cyclization-isomerization of .beta.- and .gamma.-alkynyl allylic alcohols

  摘要：

  Beta- and gamma-alkylyl allylic alcohols 3, 13, 26, available through Pd-mediated coupling of appropriate vinylic halides and terminal alkynes, cyclize and subsequently isomerize to furans 4, 17, and 32 upon treatment with KO-t-Bu in t-BuOH-THF at 25-60-degrees-C. The methodology has been used to prepare 2,3-, 2,4-, and 2,3,5-substituted furans. Reactions in t-BuOD as cosolvent lead to deuterium incorporation consistent with concurrent pathways in which direct 5-exo-dig or 5-endo-dig cyclization of the alkynyl allylic alcohol competes with prior isomerization to an allene intermediate which subsequently cyclizes by 5-exo- or 5-endo-dig pathways.

  DOI：

  10.1021/jo00064a038

文献信息

• WO2007/131834
  申请人：——

  公开号：——

  公开（公告）日：——
• Marshall James A., DuBay William J., J. Org. Chem., 58 (1993) N 12, S 3435-3443
  作者：Marshall James A., DuBay William J.

  DOI：——

  日期：——
• TRISUBSTITUTED FURAN DERIVATIVES AS FRAGRANCES AND AROMA SUBSTANCES
  申请人：Symrise GmbH & Co. KG

  公开号：EP2027101A1

  公开（公告）日：2009-02-25
• [EN] TRISUBSTITUTED FURAN DERIVATIVES AS FRAGRANCES AND AROMA SUBSTANCES<br/>[FR] DÉRIVÉS DE FURANNE TRISUBSTITUÉS COMME PARFUMS ET SUBSTANCES AROMATIQUES
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2007131834A1

  公开（公告）日：2007-11-22

  [EN] The invention concerns a use of a compound having formula (I) wherein: a first of the radicals R¹, R², R³ , R⁴ denotes hydrogen, a second of the radicals R¹, R², R³ , R⁴ denotes an alkyl or alkenyl radical having 3 to 6 C atoms, and a third and a fourth of the radicals R¹, R², R³, R⁴mutually independently denote an alkyl or alkenyl radical having 1 to 6 C atoms, as a fragrance and/or aroma substance and/or as a means of rounding out and/or of imparting vibrancy, naturalness (authenticity), fullness, complexity and/or staying power to a basic fragrance and/or aroma substance blend.
  [FR] L'invention concerne une utilisation d'un composé ayant la formule (I) dans laquelle un premier des radicaux R¹, R², R³, R⁴ représente l'hydrogène, un second des radicaux R¹, R², R³, R⁴ représente un radical alkyle ou alcényle ayant 3 à 6 atomes de carbone, et un troisième et un quatrième des radicaux R¹, R², R³, R⁴ représentent chacun indépendamment un radical alkyle ou alcényle ayant 1 à 6 atomes de carbone, comme parfum et/ou substance aromatique et/ou comme moyen pour compléter et/ou conférer l'éclat, le naturel (l'authenticité), la charpente, la complexité et/ou la tenue à un mélange de parfums et/ou substances aromatiques de base.
• Synthesis of furans by base-catalyzed cyclization-isomerization of .beta.- and .gamma.-alkynyl allylic alcohols
  作者：James A. Marshall、William J. DuBay

  DOI：10.1021/jo00064a038

  日期：1993.6

  Beta- and gamma-alkylyl allylic alcohols 3, 13, 26, available through Pd-mediated coupling of appropriate vinylic halides and terminal alkynes, cyclize and subsequently isomerize to furans 4, 17, and 32 upon treatment with KO-t-Bu in t-BuOH-THF at 25-60-degrees-C. The methodology has been used to prepare 2,3-, 2,4-, and 2,3,5-substituted furans. Reactions in t-BuOD as cosolvent lead to deuterium incorporation consistent with concurrent pathways in which direct 5-exo-dig or 5-endo-dig cyclization of the alkynyl allylic alcohol competes with prior isomerization to an allene intermediate which subsequently cyclizes by 5-exo- or 5-endo-dig pathways.