(2E/Z)-ethyl 2,3,4-trimethylpent-2-enoate | 6570-81-6

• 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: (2E/Z)-ethyl 2,3,4-trimethylpent-2-enoate
• 英文别名: 2,3,4-Trimethyl-pent-2-ensaeure-ethylester；2,3,4-Trimethyl-pentensaeure-ethylester；cis-2,3,4-Trimethyl-pent-2-ensaeure-ethylester；Ethyl 2,3,4-trimethylpent-2-enoate；ethyl 2,3,4-trimethylpent-2-enoate
• CAS: 6570-81-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: CNFKGCNFMZZNAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (2E/Z)-ethyl 2,3,4-trimethylpent-2-enoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三溴化磷 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 Acetic acid (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3,4,5-trimethyl-hexanoyl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Synthesis of cholesteol analogs with modified side-chains

  摘要：

  DOI：

  10.1016/0039-128x(66)90069-9
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 1-乙氧基-1-丙炔 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 生成 (2E/Z)-ethyl 2,3,4-trimethylpent-2-enoate
  参考文献：
  名称：

  Vieregge,H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 929 - 951

  摘要：

  DOI：

文献信息

• Contiguous Quaternary Centers from a Au ^I ‐Catalyzed Nazarov Cyclization
  作者：Jonathan Congmon、Marcus A. Tius

  DOI：10.1002/ejoc.201800604

  日期：2018.6.22

  The cationic AuI catalyzed cyclization of substituted enynes leads to cyclopentenones through a cascade of reactions. The highly diastereoselective synthesis of cyclopentenones bearing adjacent, all‐carbon atom quaternary centers is reported.

  阳离子Au I催化的取代烯炔的环化反应通过级联反应生成环戊烯酮。据报道，带有相邻的全碳原子季中心的环戊烯酮具有高度非对映选择性。
• 2-,5-,6-,7-,8-substituted oct-2-en-4-ones
  申请人：GIVAUDAN SA

  公开号：US20020176838A1

  公开（公告）日：2002-11-28

  The invention relates to 2-,5-,6-,7-,8-substituted oct-2-en-4-ones, to a process for delivering these compounds as a fragrance, an aroma, or a flavoring, and to fragrance and aroma compositions prepared therewith.

  本发明涉及2-,5-,6-,7-,8-取代的辛-2-烯-4-酮，以及将这些化合物作为香料、香气或调味剂的方法和使用这些化合物制备的香气和香气组合物。
• Iridium-Catalyzed Double Convergent 1,3-Rearrangement/Hydrogenation of Allylic Alcohols
  作者：Jianping Yang、Luca Massaro、Weigao Hu、Bram B. C. Peters、Norman Birke、Chayamon Chantana、Thishana Singh、Pher G. Andersson

  DOI：10.1021/jacs.2c11289

  日期：2023.1.11

  enantioenriched product. Here we report a novel enantioselective double convergent 1,3-rearrangement/hydrogenation of allylic alcohols using an Ir-N,P catalyst. A variety of allylic alcohols, each consisting of a 1:1:1:1 mixture of four isomers, were converted to the corresponding tertiary alcohols with two contiguous stereogenic centers, in up to 99% ee and 99:1 d.r. DFT calculations, and control experiments suggest

  对映体收敛催化有可能将起始材料的不同异构体转化为单一的高度对映体富集的产物。在这里，我们报告了一种使用 Ir-N,P 催化剂对烯丙醇进行新型对映选择性双收敛 1,3-重排/氢化反应。各种烯丙醇（每种均由四种异构体的 1:1:1:1 混合物组成）被转化为具有两个相邻立体中心的相应叔醇，最高ee为 99%， dr为99:1 。DFT 计算和控制实验表明，1,3-重排是反应的关键立体决定元素。
• Vieregge,H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 929 - 951
  作者：Vieregge,H. et al.

  DOI：——

  日期：——
• 5,6,7-Trimethylocta-2,5-dien-4-one − A Suspected Odorant with Surprising Olfactory Properties
  作者：Philip Kraft、Caroline Denis、Walter Eichenberger

  DOI：10.1002/1099-0690(200106)2001:12<2363::aid-ejoc2363>3.0.co;2-e

  日期：2001.6

  5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.