(E)-2-methylundec-2-enal | 75102-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-methylundec-2-enal
• 英文别名: (E)-2-Methyl-2-undecenal
• CAS: 75102-16-8
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: PXDFBOUIQZZHAI-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [1-((E)-2-Methoxy-1-methyl-vinyl)-nonylsulfanyl]-benzene 在 sodium periodate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以78%的产率得到(E)-2-methylundec-2-enal
  参考文献：
  名称：

  硫烷锡介导的γ-烷氧基烯丙基硫化物的制备；α，β-不饱和醛的有效β-烷基化

  摘要：

  标题β-烷基化是通过一系列α-烯醇缩醛的亚磺酰基化，-BuLi促进的烷基化和氧化水解来实现的。

  DOI：

  10.1016/0040-4039(88)85063-9

文献信息

• A Convenient Method for Conversion of Allylic Chlorides to α,β-Unsaturated Aldehydes
  作者：Shigeaki Suzuki、Takashi Onishi、Yoshiji Fujita、Hiromitsu Misawa、Junzo Otera

  DOI：10.1246/bcsj.59.3287

  日期：1986.10

  Tertiary amine N-oxides were found to be effective for converting allylic chlorides to α,β-unsaturated aldehydes.

  发现叔胺 N-氧化物可有效将烯丙基氯转化为 α,β-不饱和醛。
• CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME
  申请人：YAMADA Shinya

  公开号：US20120136176A1

  公开（公告）日：2012-05-31

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种用于通过选择性不对称加氢α，β-不饱和羰基化合物制备光学活性羰基化合物的催化剂，该催化剂在反应混合物中不溶解，并提供了制备相应光学活性羰基化合物的方法。特别地，该发明提供了一种催化剂，通过选择性不对称加氢柠檬醛、香叶醛或柠檬醛制备出用作香料或芳香剂的光学活性香茅醛。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种金属负载物质，其中至少一种金属负载在一种载体上；一种光学活性肽化合物；和一种酸，还涉及使用该催化剂制备光学活性羰基化合物的方法。
• Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs’ catalysts
  作者：Sandra M. Rountree、Sarah F.R. Taylor、Christopher Hardacre、M. Cristina Lagunas、Paul N. Davey

  DOI：10.1016/j.apcata.2014.08.032

  日期：2014.9

  A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs’ catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest

  使用格鲁布斯的催化剂，在缺电子的烯烃（即丙烯醛，巴豆醛，甲基丙烯醛和丙烯腈）与各种不同的1 -烯烃，包括1-癸烯，1-辛烯，1-己烯和2-烯丙氧基-6-甲基庚烷。后者特别受关注，因为它以前没有在交叉复分解反应中用作底物，并允许获得有价值的中间体以合成新的香料。大多数反应对所需的CM产物具有良好的选择性（≥90％）。对丙烯醛与1-癸烯的交叉复分解进行了详细的优化和机理研究。已经尝试使用离子液体来再循环催化剂。
• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Tandem-Directed Regioselective Hydroformylation/β-Elimination: A Practical Method for the Synthesis of Enals
  作者：Bernhard Breit、Achim Bruch、Antje Gebert

  DOI：10.1055/s-2008-1067140

  日期：2008.7

  A practical synthesis of α,β-unsaturated aldehydes by a tandem-directed hydroformylation/β -elimination process of allylic o-DPPB esters is reported. The o-DPPB group served as an effective controller for regioselectivity of the hydroformylation towards the desired aldolate isomer, and was subsequently eliminated in situ by mild standard bases. The reaction is rather general for the preparation of

  报道了通过烯丙基 o-DPPB 酯的串联定向加氢甲酰化/β-消除工艺实际合成 α,β-不饱和醛。o-DPPB 基团作为加氢甲酰化对所需醛醇异构体的区域选择性的有效控制剂，随后被温和的标准碱原位消除。该反应对于制备 1,1-二取代和三取代烯醛是相当普遍的，并且与许多官能团相容。o-DPPBA 可以通过色谱法或以二乙基铵盐的形式沉淀来回收。