(R)-(+)-2,6-dimethyl-8-acetoxyoct-2-enal | 98168-98-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(+)-2,6-dimethyl-8-acetoxyoct-2-enal
• 英文别名: (R)-(E)-7-formyl-3-methyloct-6-enyl acetate；[(E,3R)-3,7-dimethyl-8-oxooct-6-enyl] acetate
• CAS: 98168-98-0
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: HEUSWAZSUJSVCG-VUUNSECVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2,6-dimethyl-8-acetoxyoct-2-enal 以 水 为溶剂， 反应 72.0h， 以35%的产率得到(2S,6R)-(-)-2,6-dimethyl-8-acetoxyoctan-1-ol
  参考文献：
  名称：

  Chiral synthetic intermediates via asymmetric hydrogenation of .alpha.-methyl-.alpha.,.beta.-unsaturated aldehydes by bakers' yeast

  摘要：

  DOI：

  10.1021/jo00223a038
• 作为产物：
  描述：

  (R)-1-citronellyl acetate 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 甲苯 为溶剂， 反应 120.0h， 生成 (R)-(+)-2,6-dimethyl-8-acetoxyoct-2-enal
  参考文献：
  名称：

  The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways

  摘要：

  Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactune, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by H-1 and C-13 NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00012-0

文献信息

• Efficient catalyst for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels–Alder reactions
  作者：Sylvia Fernandes、P. Rajakannu、Sujata V. Bhat

  DOI：10.1039/c5ra09865c

  日期：——

  Tandem Knoevenagel-cycloaddition reactions forming bicyclic tetrahydro-2H-chromen-5(6H)-ones and tricyclic octahydro-2H-benzo[c]-chromen-1(6H)-ones are achieved with up to 98.8% ee in the presence of chiral LBA and titanium-isopropoxy-(S)-BINOLate.

  Knoevenagel串联环加成反应形成双环四氢-2H-色滨-5(6H)-酮和三环八氢-2H-苯并[c]-色滨-1(6H)-酮，在手性LBA和钛异丙氧基-(S)-BINOLate存在下，可实现高达98.8%的对映选择性。
• Studies directed toward the total synthesis of cerorubenic acid-III. 3. A convergent enantioselective approach involving new arrangements for the actuation of ring D cyclization
  作者：Leo A. Paquette、David N. Deaton、Yasuyuki Endo、Marc Andre Poupart

  DOI：10.1021/jo00068a021

  日期：1993.7

  A possible enantiocontrolled route to cerorubenic acid-III (1) is described herein. The central elements of the approach take advantage of the ready availability of both optical an of citronellol and of the tricyclic ketone 8. Although the absolute configuration of 1 is not known, its relative stereochemistry has been established by X-ray crystallography. On this basis, it is possible to match the reaction partners with the long-range view of establishing experimentally the actual configuration of 1. Assembly of the two structural halves was accomplished via a vinylstannane intermediate whose construction required utilization of an intramolecular S(N)2 displacement in order to overcome the weakly nucleophilic nature of a stannyl-substituted ester enolate. The coupling reaction leading to 38 and 39 proved highly stereoselective as before, thereby setting the stage for conversion to D-seco derivatives of 1 via anionic oxy-Cope rearrangement. Although this phase of the strategy had previously been worked out on simpler systems, 38, 39, and analogs therof isomerized with concomitant alpha-hydroxylation of the intermediate enolates. These conversions proceeded smoothly and efficiently. Although conditions were found that curtailed this adventitious oxygenation, the conversions proceeded so slowly that degradation was now competitive with the formation of 41 and 43.
• GRAMATICA, P.;MANITTO, P.;POLI, L., J. ORG. CHEM., 1985, 50, N 23, 4625-4628
  作者：GRAMATICA, P.、MANITTO, P.、POLI, L.

  DOI：——

  日期：——