3,4,4-三甲基-戊-2-烯醛 | 144562-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4,4-三甲基-戊-2-烯醛
• 英文名称: 3,4,4-Trimethyl-penten-(2)-al
• 英文别名: 3,4,4-Trimethylpent-2-enal
• CAS: 144562-22-1
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: RJURJJIOVZPPRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3,4,4-三甲基-戊-2-烯醛 在 potassium hexacyanoferrate(III) 作用下， 生成 3-tert.-Butyl-crotonsaeure
  参考文献：
  名称：

  Sung, Annales de Chimie (Cachan, France), 1924, vol. <10>1, p. 364

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3,4,4-trimethylpent-2-en-1-ol 在 chromium(III) oxide 、 硫酸 作用下， 生成 3,4,4-三甲基-戊-2-烯醛
  参考文献：
  名称：

  Sung, Annales de Chimie (Cachan, France), 1924, vol. <10>1, p. 364

  摘要：

  DOI：

文献信息

• 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。
• ORGANIC SALTS AND METHOD FOR PRODUCING CHIRAL ORGANIC COMPOUNDS
  申请人：List Benjamin

  公开号：US20090030216A1

  公开（公告）日：2009-01-29

  The invention relates to a method for producing chiral organic compounds by asymmetric catalysis, using ionic catalysts comprising a chiral catalyst anion. The claimed method is suitable for reactions which are carried out over cationic intermediate stages, such as iminium ions or acyl pyridinium ions. The invention enables the production of chiral compounds with high ee values, that until now could only be obtained by means of costly purification methods.

  该发明涉及一种通过不对称催化制备手性有机化合物的方法，使用包括手性催化剂阴离子的离子催化剂。所述方法适用于在阳离子中间体阶段进行的反应，例如亚胺离子或酰基吡啶离子。该发明实现了具有高ee值的手性化合物的生产，直到现在只能通过昂贵的纯化方法获得。
• 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。
• Organocatalytic Enantioselective Cycloaddition Reactions of Dienamines with Quinones
  作者：Tore Kiilerich Johansen、Clarisa Villegas Gómez、Jesper R. Bak、Rebecca L. Davis、Karl Anker Jørgensen

  DOI：10.1002/chem.201303526

  日期：2013.12.2

  Matching catalyst and substrate: Organocatalytic cycloaddition between dienamines and 1,4‐benzo‐ or 1,4‐naphthoquinones affords biologically interesting dihydronaphtho‐ and dihydroanthraquinone core structures. The enantioselectivity of this new reaction is ensured by a steric shielding catalyst and carefully selecting substrates that greatly favor the endo approach (see scheme) due to electrostatic

  匹配的催化剂和底物：二烯胺和1,4-苯并或1,4-萘醌之间的有机催化环加成反应提供了生物学上令人感兴趣的二氢萘和二氢蒽醌核心结构。该新反应的对映选择性是通过空间屏蔽催化剂和精心选择的底物来确保的，该底物由于两性离子中间体中的静电相互作用而极大地支持了内切法（参见方案）。
• Carbene-Catalyzed α,γ-Deuteration of Enals under Oxidative Conditions
  作者：Xiaolei Zhang、Qiao Chen、Runjiang Song、Jun Xu、Weiyi Tian、Shaoyuan Li、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acscatal.0c00636

  日期：2020.5.15

  azolium ester formation, remote γ-carbon activation, reversible α- and γ-carbon enolization, and iterative H/D exchanges. The reaction is performed under mild conditions using D2O as the deuterium source to efficiently afford α,γ-deuterated 2-alkenoic acids and their derivatives in good to excellent yields and high deuterium incorporation. These labeled products containing carbonyl and allyl bifunctionalities

  带有氘代烯丙基的有机化合物对于增强药物代谢动力学特性的药物实体非常有吸引力，因为烯丙基的C–H键容易发生代谢氧化，而氘代化合物则较不容易发生这种代谢。然而，在烯丙基C–H部分直接氘化仍然是一个挑战。过渡金属催化的报道很少，而有机催化的报道也没有。在这里，烯丙基C（sp 3）和C（sp 2）的烯的卡宾催化的CH重氢）中心已公开。将卡宾催化剂加到烯醛的醛部分上以在氧化条件下最终活化α和γ碳原子对于实现高氘掺入至关重要。我们反应的关键机理步骤包括卡宾催化剂的添加，偶氮酯的形成，远程γ-碳活化，可逆的α-和γ-碳烯化反应以及H / D迭代交换。反应在温和条件下使用D 2进行使用O作为氘源，可以以良好至极好的收率和高氘掺入率高效提供α，γ氘代的2-链烯酸及其衍生物。这些含有羰基和烯丙基双官能团的标记产物是进一步转化的有价值的构建基块，最终导致具有挑战性的标记靶标，包括氘代烯丙基衍生物，脂族衍生物和多