3-methyl-6-oxohex-1-en-3-yl acetate | 153073-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-6-oxohex-1-en-3-yl acetate
• 英文别名: 4-(acetyloxy)-4-methyl-5-hexenal；4-Acetoxy-4-methyl-5-hexenal；5-Hexenal, 4-(acetyloxy)-4-methyl-, (+/-)-；(3-methyl-6-oxohex-1-en-3-yl) acetate
• CAS: 153073-81-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: XMMGLIMEHNSBSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  238.0±33.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-methyl-6-oxohex-1-en-3-yl acetate 在 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 ethyl 2-(5-methyl-5-vinyltetrahydrofuran-2-yl)acetate
  参考文献：
  名称：

  Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes

  摘要：

  Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Bronsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.030
• 作为产物：
  描述：

  芳樟醇 在 4-二甲氨基吡啶 、 三乙胺 、 间氯过氧苯甲酸 作用下， 反应 2.0h， 生成 3-methyl-6-oxohex-1-en-3-yl acetate
  参考文献：
  名称：

  由细胞毒性皂苷合成二聚萜烯酰基糖苷侧链。

  摘要：

  DOI：

  10.1002/anie.200352895

文献信息

• Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M4(H2O)2(PW9O34)2]n−, M = CoII, MnII and FeIII
  作者：Isabel C.M.S. Santos、José A.F. Gamelas、Tiago A.G. Duarte、Mário M.Q. Simões、M. Graça P.M.S. Neves、José A.S. Cavaleiro、Ana M.V. Cavaleiro

  DOI：10.1016/j.molcata.2016.10.021

  日期：2017.1

  7-double bond for Mn4(PW9)2, affording 6,7-epoxide at 82% selectivity. Linalyl acetate 1,2-epoxide was the major product with 51% and 77% selectivity for Co4(PW9)2 and Fe4(PW9)2, respectively. Oxidation of carveol occurred with very good conversions in the presence of Mn4(PW9)2, Co4(PW9)2 and Fe4(PW9)2, yielding carvone and carveol 1,2-epoxide in similar amounts. Oxidation of cis-cyclooctene gave only the

  研究了夹心钨磷酸盐B-α-[M 4（H 2 O）2（PW 9 O 34）2 ] n-（M = Co II，Mn II，Fe III）的四丁基铵盐在（- ）的氧化中的催化效率R）-（+）-柠檬烯，香叶醇，芳樟醇，乙酸芳樟酯，香芹酚和顺式-环辛烯与过氧化氢的乙腈溶液。（R的氧化）-（+）-柠檬烯得到柠檬烯-1,2-二醇作为主要产物。芳樟醇的环氧化反应优先发生在取代度更高的6,7-双键上，相应的6,7-环氧化物进一步反应，通过分子内环化反应生成呋喃-和吡喃氧化物。乙酸芳樟酯的氧化优先发生在Mn 4（PW 9）2的更取代的6,7-双键处，以82％的选择性提供6,7-环氧。乙酸芳基酯1,2-环氧化物是主要产物，对Co 4（PW 9）2和Fe 4（PW 9）2的选择性分别为51％和77％。在锰的存在下，香芹酚的氧化转化率很高4（PW 9）2，Co 4（PW 9）2和Fe 4（PW 9）2产生类似量的香芹酮和香芹酚1
• Stereoselective synthesis of the proposed American coneflower juvenile hormone mimic. Some observations on the cyclopropylcarbinyl rearrangement in substituted systems
  作者：Manning P. Cooke

  DOI：10.1021/jo01328a027

  日期：1979.7
• JPH05339252A
  申请人：——

  公开号：JPH05339252A

  公开（公告）日：1993-12-21
• Synthesis of Dimeric Terpenoyl Glycoside Side Chains from Cytotoxic Saponins
  作者：Sabine Reicheneder、Carlo Unverzagt

  DOI：10.1002/anie.200352895

  日期：2004.8.20
• Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes
  作者：Peter Šiška、Peter Fodran、Peter Szolcsányi

  DOI：10.1016/j.tet.2014.07.030

  日期：2014.9

  Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Bronsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds. (C) 2014 Elsevier Ltd. All rights reserved.