(E)-3,7-dimethyl-8-oxooct-6-enyl acetate | 79763-09-0

• 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: (E)-3,7-dimethyl-8-oxooct-6-enyl acetate
• 英文别名: 8-oxo-3,7-Dimethyl-6E-octenyl acetate；[(E)-3,7-dimethyl-8-oxooct-6-enyl] acetate
• CAS: 79763-09-0
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: HEUSWAZSUJSVCG-IZZDOVSWSA-N

物化性质

• 沸点：
  316.2±35.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

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：

  (E)-3,7-dimethyl-8-oxooct-6-enyl acetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (E)-2,6-dimethyloct-2-ene-1,8-diol
  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
• 作为产物：
  描述：

  乙酸香茅酯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以85%的产率得到(E)-3,7-dimethyl-8-oxooct-6-enyl acetate
  参考文献：
  名称：

  微波辐射下固体载体上烯丙基甲基的选择性氧化†

  摘要：

  发现吸附在 SiO 2 上的 SeO 2 /Bu t OOH 是一种高选择性试剂，用于在微波辐射下将烯丙基甲基氧化为反式-α,β-不饱和醛。

  DOI：

  10.1039/a700758b

文献信息

• Preparation of conjugated carbonyl compounds by photolysis of η₃-allylpalladium complexes
  作者：Jacques Muzart、Patrick Pale、Jean-Pierre Pete

  DOI：10.1039/c39810000668

  日期：——

  Irradiation at 366 nm of oxygenated solutions of η3-allylpalladium complexes leads to unsaturated carbonyl compounds.

  照射在氧化溶液的366nm的η 3所π-烯丙基配合物导致的不饱和羰基化合物。
• Total Synthesis of an Antifouling Marine Furanosesquiterpene
  作者：S. Murphree、Chad Ungarean、Jeremy Mason、Benjamin Eyer、Nicholas Duca、Jaimie Mong

  DOI：10.1055/s-0036-1588711

  日期：——

  Abstract An antifouling sesquiterpene isolated from Sinularia sp. was synthesized from citronellyl acetate in eight steps and 9% overall yield. The furan moiety was constructed using a multifunctional sulfone reagent. An antifouling sesquiterpene isolated from Sinularia sp. was synthesized from citronellyl acetate in eight steps and 9% overall yield. The furan moiety was constructed using a multifunctional

  摘要 从Sinularia sp。分离的防污倍半萜。由乙酸香茅酯以八步合成，总收率为9％。使用多功能砜试剂构建呋喃部分。 从Sinularia sp。分离的防污倍半萜。由乙酸香茅酯以八步合成，总收率为9％。使用多功能砜试剂构建呋喃部分。
• Muzart, J.; Pale, P.; Pete, J.P., Bulletin de la Societe Chimique de France, 1988, # 4, p. 731 - 739
  作者：Muzart, J.、Pale, P.、Pete, J.P.、Riahi, A.

  DOI：——

  日期：——
• Speedy and Regioselective 1,2-Reduction of Conjugated α,β-Unsaturated Aldehydes and Ketones Using NaBH₄/I₂
  作者：Jasvinder Singh、Irvinder Kaur、Jasamrit Kaur、Aman Bhalla、Goverdhan L. Kad

  DOI：10.1081/scc-120015699

  日期：2003.3

  Synthesis of allylic alcohols from alpha,beta-unsaturated aldehydes/ketones has been achieved in excellent yields utilizing NaBH4 and iodine. This reducing agent is mild and tolerant to a number of functional groups.
• SINGH, JASVINDER;SABHARWAL, ARUN;SAYAL, PARDEEP K.;CHHABRA, BALDEV R., CHEM. AND IND.,(1989) N6, C. 533-534
  作者：SINGH, JASVINDER、SABHARWAL, ARUN、SAYAL, PARDEEP K.、CHHABRA, BALDEV R.

  DOI：——

  日期：——