(2,2,4-三甲基-3-环戊烯-1-基)乙醛 | 3899-09-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2,2,4-三甲基-3-环戊烯-1-基)乙醛
• 英文名称: isocampholenic aldehyde
• 英文别名: fencholenic aldehyde；Fencholenaldehyd；(2,2,4-Trimethylcyclopent-3-en-1-yl)acetaldehyde；2-(2,2,4-trimethylcyclopent-3-en-1-yl)acetaldehyde
• CAS: 3899-09-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: DHLICSPYERWBQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,2,4-三甲基-3-环戊烯-1-基)乙醛 在 氢氧化钾 、 乙二醇 、 肼 作用下， 以83%的产率得到Cyclopentene, 4-ethyl-1,3,3-trimethyl-, (S)-
  参考文献：
  名称：

  铑催化的光学活性喜树碱类似物的脱羰作用

  摘要：

  用催化量的Rh / Al 2 O 3进行去羰基化的喜树碱类似物（+）- 1a–d，仅出现少量外消旋作用。用其他催化剂进行的实验表明，外消旋作用随金属形成π-烯丙基络合物和催化β-消除副产物氢化的能力而增加。（Ph 3 P）3 RhCl效果最佳。

  DOI：

  10.1016/s0040-4039(00)60025-4
• 作为产物：
  描述：

  R-alpha-(+)-蒎烯氧化物 在 氢溴酸 、 silver nitrate 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 (2,2,4-三甲基-3-环戊烯-1-基)乙醛
  参考文献：
  名称：

  Aminium salts catalyzed rearrangement of α-pinene and β-ionone oxides

  摘要：

  beta-ionone and alpha-pinene oxides 1, 3 isomerize rapidly and selectively to 1-(1,2,2-trimethylcyclopent-1-yl)-pent-2-en-1.4-dione 2 and the industrially important 2,2,3-trimethyl-3-cyclopentene acetaldehyde 4. under the influence of catalytic amounts of aminium salts A,B. In order to find insights into the mechanism of our procedure, protic and Lewis acids-catalyzed rearrangements have also been reconsidered.

  DOI：

  10.1016/s0040-4020(01)85375-8

文献信息

• Influence of the Brönsted and Lewis acid sites on the catalytic activity and selectivity of Fe/MCM-41 system
  作者：N.A. Fellenz、J.F. Bengoa、S.G. Marchetti、A. Gervasini

  DOI：10.1016/j.apcata.2012.06.003

  日期：2012.9

  spectroscopy. The influence of the structural changes of the nanoclusters and the effect of the simultaneous presence of Lewis and Brönsted acid sites were evaluated studying the product distribution from the α-pinene oxide isomerization reaction. It was determined that the Brönsted acidity of the Fe/MCM-41 system has not the sufficient acid strength to modify the product distribution which is mainly governed

  合成具有高铁分散性的系统Fe 2 O 3 / MCM-41，以将路易斯酸位引入MCM-41结构中。两种煅烧气氛（惰性和氧化剂）用于生产具有不同结构特性的铁纳米团簇。此外，在两种固体上均实现了甲硅烷基化处理，目的是中和与MCM-41硅烷醇基团相关的布朗斯台德酸度。通过原子吸收光谱，低角度X射线衍射，N 2吸附，程序升温还原，傅里叶变换红外光谱，29个核磁共振对样品进行表征Si和Mössbauer光谱。研究了α-pine烯氧化物异构化反应的产物分布，评估了纳米团簇的结构变化的影响以及路易斯和布朗斯台德酸位点同时存在的影响。已经确定，Fe / MCM-41系统的布朗斯台德酸度没有足够的酸强度来改变主要由路易斯位点控制的产物分布。
• Copper(II) tetrafluroborate-promoted Meinwald rearrangement reactions of epoxides
  作者：Mathew W.C. Robinson、Kathryn S. Pillinger、Ian Mabbett、David A. Timms、Andrew E. Graham

  DOI：10.1016/j.tet.2010.08.078

  日期：2010.10

  Epoxides undergo a highly efficient Meinwald rearrangement in the presence of catalytic quantities of copper(II) tetrafluoroborate to give carbonyl compounds in high yields and with excellent selectivity. The low toxicity and ease of handling of this reagent make it an attractive alternative to the more corrosive or costly Lewis acids frequently employed.

  在催化量的四氟硼酸铜（II）的存在下，环氧树脂会进行高效的Meinwald重排，从而以高收率和优异的选择性得到羰基化合物。该试剂的低毒性和易处理性使其成为经常使用的更具腐蚀性或成本较高的路易斯酸的诱人替代品。
• Synthesis of Fencholenic Aldehyde from α-pinene Epoxide on Modified Clays
  作者：A. Yu. Sidorenko、Zh. V. Ignatovich、A. L. Ermolinskaya、A. V. Kravtsova、A. V. Baranovskii、E. V. Koroleva、V. E. Agabekov

  DOI：10.1007/s10600-018-2506-9

  日期：2018.9

  The conditions for isomerization of α-pinene epoxide (2,3-epoxypinane) on modified clays that gave comparatively high contents (33.0%) of fencholenic (iso-campholenic) aldehyde in the product mixture were determined. An effective method for isolating it was proposed. The structure of iso-campholenic aldehyde was confirmed by analyzing 2D NOESY and HMBC NMR spectra.

  改性粘土上α-蒎烯环氧化物（2,3-环氧蒎烷）异构化的条件被确定，这些条件在产物混合物中产生了相对较高含量的（33.0%）小茴香醛（异荍烷醛）。提出了一种有效的分离方法。通过分析2D NOESY和HMBC NMR谱图确认了异茴香醛的结构。
• Three-Component Reaction Using the Bestmann-Ohira Reagent: A Regioselective Synthesis of Phosphonyl Pyrazole Rings
  作者：Kishor Mohanan、Anthony R. Martin、Loic Toupet、Michael Smietana、Jean-Jacques Vasseur

  DOI：10.1002/anie.200906781

  日期：2010.4.19

  to run: A new one‐pot multicomponent reaction involving the use of an aldehyde, a cyanoacid derivative, and the Bestmann–Ohira reagent (BOR) has been developed for the synthesis of substituted phosphonyl pyrazoles. This process was also combined with a copper‐catalyzed azide–alkyne 1,3‐dipolar cycloaddition to generate five new bonds and two heterocyclic rings in a one‐pot fashion.

  即将运行的BOR-n：已开发出一种新的单锅多组分反应，该反应涉及使用醛，氰酸衍生物和Bestmann-Ohira试剂（BOR）来合成取代的膦酰基吡唑。此过程还与铜催化的叠氮化物-炔烃1,3-偶极环加成反应相结合，以一锅法生成五个新键和两个杂环。
• [EN] NOVEL AROMA CHEMICALS HAVING A 1,2,2-TRIMETHYLCYCLOPENTAN-1-YL MOIETY<br/>[FR] NOUVEAUX ARÔMES CHIMIQUES PRÉSENTANT UNE FRACTION 1,2,2-TRIMÉTHYLCYCLOPENTAN-1-YLE
  申请人：BASF SE

  公开号：WO2016193133A1

  公开（公告）日：2016-12-08

  The present invention relates to novel compounds of general formulae (la), (lb) and (Ic) and to the stereoisomers thereof. The compounds are useful as a fragrance or as flavor as they have a sandalwood like scent. The invention also relates to a method for imparting or modifying a scent or a flavor to a composition by including said compounds into such composition, to a fragrance containing composition and/or a fragrance material containing said compound and to a process for preparing these compounds. X is C(R4)-OH or C=O; R1 is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4- alkenyl and C3-C4-cycloalkyl, R2 is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4- alkenyl and C3-C4-cycloalkyl, R3 is C1-C4-alkyl, R3a is selected from the group consisting of hydrogen and C1-C4-alkyl, R3b is hydrogen or together with R3a is CH2; R4 is selected from the group consisting of hydrogen and C1-C4-alkyl.

  本发明涉及一般式（Ia）、（Ib）和（Ic）的新化合物及其立体异构体。这些化合物可用作香精或调味剂，因为它们具有类似檀香的香味。该发明还涉及一种通过将这些化合物包含在组合物中来赋予或修改香味或口味的方法，涉及一种含有这些化合物的香精组合物和/或含有该化合物的香精材料，以及制备这些化合物的方法。X为C（R4）-OH或C=O；R1选自氢、C1-C4烷基、C2-C4烯基和C3-C4环烷基组成的群；R2选自氢、C1-C4烷基、C2-C4烯基和C3-C4环烷基组成的群；R3为C1-C4烷基，R3a选自氢和C1-C4烷基，R3b为氢或与R3a一起为CH2；R4选自氢和C1-C4烷基。