(E)-ethyl 4,8-dimethyl-3,7-nonadienoate | 99722-93-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-ethyl 4,8-dimethyl-3,7-nonadienoate
• 英文别名: Homogeranic acid ethyl ester；ethyl 4,8-dimethyl-(3E)-3,7-nonadienoate；Ethyl-geranat；ethyl (3E)-4,8-dimethyl-3,7-nonadienoate；ethyl (3E)-4,8-dimethylnona-3,7-dienoate
• CAS: 99722-93-7
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: BXQLAXIZPLEGMU-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (E)-ethyl 4,8-dimethyl-3,7-nonadienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以70%的产率得到(3Z)-4,8-二甲基-3,7-壬二烯-1-醇
  参考文献：
  名称：

  Vig, O. P.; Trehan, I. R.; Kad, G. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 5, p. 515 - 516

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 、 乙醇 以76%的产率得到
  参考文献：
  名称：

  Murahashi Shun-Ichi, Imada Yasushi, Taniguchi Yuki, Higashiura Shinya, J. Org. Chem, 58 (1993) N 6, S 1538-1545

  摘要：

  DOI：

文献信息

• Palladium(0)-catalyzed carbonylation of allyl phosphates and allyl acetates. Selective synthesis of β,γ-unsaturated esters
  作者：Shun-Ichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shin-ya Higashiura

  DOI：10.1016/s0040-4039(00)80648-6

  日期：1988.1

  Palladium catalyzed carbonylations of allyl phosphates and allyl acetates give β,γ-unsaturated esters efficiently. The latter reaction requires bromide ion as a co-catalyst.

  钯催化的烯丙基磷酸酯和乙酸烯丙酯的羰基化反应可有效地生成β，γ-不饱和酯。后一反应需要溴离子作为助催化剂。
• A Concise Synthesis of <i>rac</i> ‐ <i>Ambrox</i> ® <i>via</i> the Palladium(0)‐Catalyzed Carboalkoxylation of an Allylic Ammonium Salt, as Compared to a Formaldehyde Hetero <i>Diels–Alder</i> Approach
  作者：Christian Chapuis、David Skuy、Claude‐Alain Richard

  DOI：10.1002/hlca.201900097

  日期：2019.7

  followed by a 1.5 mol‐% Pd‐catalyzed carbomethoxylation of quaternized 31b, leads to the methyl ester 36a. This latter could also be obtained in optically pure form by carbomethoxylation of the corresponding (+)‐acetate. Final reduction‐cyclization may be conducted as earlier described, towards the desired odoriferous rac‐Ambrox® 38a, or its pure (−)‐enantiomer. Generation of a π‐allyl Pd complex from an allylic

  对二乙基烯丙胺29b或30进行酸性环化，然后进行季铵化31b的1.5 mol％Pd催化的碳甲氧基化反应，生成甲酯36a。后者也可以通过相应的（+）-乙酸酯的碳甲氧基化以光学纯净的形式获得。如上所述，朝向期望有气味的最终还原的环化可以进行外消旋-艾姆罗克斯® 38A，或它的纯的（ - ） -对映体。由烯丙基铵盐生成π烯丙基Pd络合物，然后进行碳烷氧基化是新颖的。从法呢烯2开始仅需五个化学步骤，目前的工作构成的最简洁的全合成外消旋-艾姆罗克斯® 38A是最新的。
• Palladium(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates
  作者：Shunichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shinya Higashiura

  DOI：10.1021/jo00058a040

  日期：1993.3

  Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50-degrees-C proceeds highly efficiently to give the corresponding beta,gamma-unsaturated esters. The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50-degrees-C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively. The carbonylation takes place at the least substituted allylic positions with inversion of configuration. Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl 2-cyclohexene-1,5-dicarboxylate (trans-17) selectively. Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give pi-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
• One-step conversion of terminal acetylenes into terminally functionalized (E)-3-methyl-2-alkenes via zircomium-catalyzed carboalumination. A simple and selective route to terpenoids
  作者：Nobuhisa Okukado、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(01)94773-2

  日期：1978.1
• Synthesis of new unsaturated esters, catalysed by Palladium-phosphine complexes
  作者：G. Mignani、F. Grass、M. Aufrand、D. Morel

  DOI：10.1016/s0040-4039(01)80405-6

  日期：——