1-acetoxy-3,7-dimethyloct-2-en-6-one | 1891-58-3

• 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: 1-acetoxy-3,7-dimethyloct-2-en-6-one
• 英文别名: 2,6-dimethyl-8-acetoxy-6-octen-3-one；3,7-dimethyl-6-oxo-2-octenyl acetate；6-Keto-dihydrogeranylacetat；8-Acetoxy-2,6-dimethyl-oct-6t-en-3-on；(E)-8-acetoxy-2,6-dimethyl-oct-6-en-3-one；6-oxo-6,7-dihydro-geranyl acetate；[(E)-3,7-dimethyl-6-oxooct-2-enyl] acetate
• CAS: 1891-58-3
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: WPSAOXZUSCGGKN-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-acetoxy-3,7-dimethyloct-2-en-6-one 在 sodium hydroxide 作用下， 生成 (E)-8-hydroxy-2,6-dimethyl-oct-6-en-3-one
  参考文献：
  名称：

  涉及格利雅中间体的氢化物转移。新型的反讽III（1）。

  摘要：

  DOI：

  10.1016/0040-4039(64)83142-7
• 作为产物：
  描述：

  (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate 在 三氟化硼 作用下， 以 苯 为溶剂， 生成 1-acetoxy-3,7-dimethyloct-2-en-6-one
  参考文献：
  名称：

  Mousseron-Canet,M. et al., Bulletin de la Societe Chimique de France, 1964, p. 297 - 300

  摘要：

  DOI：

文献信息

• Catalytic Coupling of Carbon Dioxide with Terpene Scaffolds: Access to Challenging Bio-Based Organic Carbonates
  作者：Giulia Fiorani、Moritz Stuck、Carmen Martín、Marta Martínez Belmonte、Eddy Martin、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/cssc.201600238

  日期：2016.6.8

  oxides and carbon dioxide into bio‐based cyclic organic carbonates catalyzed by Al(aminotriphenolate) complexes is reported. Both acyclic as well as cyclic terpene oxides were used as coupling partners, showing distinct reactivity/selectivity behavior. Whereas cyclic terpene oxides showed excellent chemoselectivity towards the organic carbonate product, acyclic substrates exhibited poorer selectivities

  据报道，高取代度的萜烯氧化物和二氧化碳难以结合到铝（氨基三酚盐）配合物催化的生物基环状有机碳酸酯中。无环和环状萜烯氧化物均用作偶联伴侣，表现出不同的反应性/选择性行为。环状萜烯氧化物对有机碳酸酯产物表现出优异的化学选择性，而无环底物由于伴随的环氧化物重排反应和不希望的低聚/聚醚副产物的形成而显示出较差的选择性。考虑到这些偶联反应的挑战性，目标生物碳酸盐的分离产率是合理的，在大多数情况下为50-60％。
• Chemical Transformation of Terpenoids. VIII. Anodic Oxidation of Geranyl Acetate.
  作者：Hirotaka SHIBUYA、Nobutoshi MURAKAMI、Fukiko SHIMADA、Isao KITAGAWA

  DOI：10.1248/cpb.39.1302

  日期：——

  Constant-current electrolysis of geranyl acetate (2) in CH3CN-H2O afforded eight oxidation products (3-10) which were presumed to be formed through initial oxidation of the double bond at C6-C7. Based on the results of electrolysis of 2 in CH3CN-H218O, we have found that the oxygen atom(s) in the products (3-10) is(are) derived from water used as the reaction medium.

  在CH3CN-H2O中对乙酸香荆芥进行恒电流电解得到八种氧化产物（3-10），这些产物据信是通过对C6-C7双键的初始氧化形成的。基于在CH3CN- 中对2的电解结果，我们发现产物（3-10）中的氧原子来自于作为反应介质的水。
• Synthesis of (±)-karahana ether and karahanaenone by selective cyclization of 6,7-epoxygeranyl acetate
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、P.Linares Palomino

  DOI：10.1016/s0040-4020(01)89332-7

  日期：1994.1

  Efficient methods for preparing (±)-karahana ether (1b) and karahanaenine (2) from 6,7-epoxygeranyl acetate(3), by Lewis-acid-catalyzed electrophillic cyclization, are described.

  描述了通过路易斯酸催化的亲电环化由6,7-环氧香叶基乙酸酯（3）制备（±）-卡拉汉纳醚（1b）和卡拉汉宁（2）的有效方法。
• Interaction of 6,7-epoxygeranyl acetate and of 10,11-epoxy-(E,E)-farnesyl acetate with fluorosulfonic acid
  作者：N. D. Ungur、N. P. Popa、P. F. Vlad

  DOI：10.1007/bf00630209

  日期：1993.9
• ——
  作者：T. M. Khomenko、D. V. Korchagina、V. A. Barkhash

  DOI：10.1023/a:1012449228670

  日期：——

  2,3-Epoxygeraniol undergoes dissimilar rearrangements in contact with liquid superacids at low temperature or on solid superacids at room temperature due to different location of the arising cationic center depending on the superacid character. 2,3-Epoxynerol, 6,7-epoxycitronellol, and 6,7-geranyl acetate on ZrO2SO42 afford the corresponding ketones via epoxy ring opening followed by 1,2-hydride shift. With 6,7-geranyl acetate 7-oxanobornane formed as a minor product. The mode of generation of the cationic center (either the olefin protonation or the epoxy ring opening) affects the rearrangement direction at similar conditions.