(Z)-ethyl 4,8-dimethyl-3,7-nonadienoate | 99722-92-6

• 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: (Z)-ethyl 4,8-dimethyl-3,7-nonadienoate
• 英文别名: ethyl 4,8-dimethyl-(3Z)-3,7-nonadienoate；ethyl (3Z)-4,8-dimethylnona-3,7-dienoate
• CAS: 99722-92-6
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: BXQLAXIZPLEGMU-XFXZXTDPSA-N

物化性质

• 沸点：
  277.1±19.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

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：

  (Z)-ethyl 4,8-dimethyl-3,7-nonadienoate 生成 (3Z)-4,8-二甲基-3,7-壬二烯-1-醇
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-4,8-dimethylnona-3,7-dienoic acid 生成 (Z)-ethyl 4,8-dimethyl-3,7-nonadienoate
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• 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.
• Kiji, Jitsuo; Okano, Tamon; Konishi, Hisatoshi, Chemistry Letters, 1989, p. 1873 - 1876
  作者：Kiji, Jitsuo、Okano, Tamon、Konishi, Hisatoshi、Nishiumi, Wataru

  DOI：——

  日期：——
• MIGNANI, G.;GRASS, F.;AUFRAND, M.;MOREL, D., TETRAHEDRON LETT., 30,(1989) N8, C. 2383-2386
  作者：MIGNANI, G.、GRASS, F.、AUFRAND, M.、MOREL, D.

  DOI：——

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

  DOI：——

  日期：——