(2E,4E)-3-tert-Butyl-5-phenyl-2,4-pentadienal | 168071-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-3-tert-Butyl-5-phenyl-2,4-pentadienal
• 英文别名: (2E,4E)-3-tert-butyl-5-phenylpenta-2,4-dienal
• CAS: 168071-58-7
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: PRHCSASIPLPAHV-QDCWQMMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  仲丁胺 、 (2E,4E)-3-tert-Butyl-5-phenyl-2,4-pentadienal 在 4 A molecular sieve 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  6.pi.-Electrocyclization of 1-Azatrienes to 1,2-Dihydropyridines

  摘要：

  A series of alpha,beta-cis-dienals were synthesized by oxidation and then in situ isomerization of easily available beta-allenic alcohols. Subsequent reaction between the alpha,beta-cis-dienals and primary amines represents a simple and useful method for the direct preparation of 1,2-dihydropyridines. Reactivity profiles and activation parameters for the cyclization of alpha,beta-cis-dienimines are similar to those of the carbocyclic counterparts except the reaction is much faster. Despite the lack of a clear stereochemical label, the disrotatory nature of the ring closure is illustrated by the greater cyclization rates of 8'c and 8'd as compared to 7'c and 7'd, respectively. The observation that sterically more hindered systems (8'c and 8'd) cyclize faster than less hindered ones (7'c and 7'd) is a feature of 6 pi-electrocyclizations that is unprecedented.

  DOI：

  10.1021/jo00111a039
• 作为产物：
  描述：

  C₁₇H₂₂O₂ 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.99h， 生成 (2E,4E)-3-tert-Butyl-5-phenyl-2,4-pentadienal
  参考文献：
  名称：

  通过逻辑底物设计控制乙烯基离子的分子拓扑：线性和2,4-二烯醛的高区域和立体选择性氨基催化1,6-加成

  摘要：

  有关拓扑控制的所有内容：标题反应可产生有价值的四氢呋喃螺硫醇（参见方案； TMS =三甲基甲硅烷基），并例举了罕见的不对称1,6加成反应，对线性2,4二烯进行高δ位和立体选择性的过程。β-二烯基位置上的一个转向基团确保了催化活性的乙烯基亚胺基离子中间体的分子预组织，从而可高度预测反应结果。

  DOI：

  10.1002/anie.201305870

文献信息

• Ambient Synthesis of Dienals via Triazole–Gold and Amine Catalysis Relay
  作者：Stephen E. Motika、Qiaoyi Wang、Xiaohan Ye、Xiaodong Shi

  DOI：10.1021/ol503393a

  日期：2015.1.16

  A highly efficient synthesis of substituted conjugated dienals was developed through a triazole–gold (TA–Au)-catalyzed propargyl vinyl ether rearrangement followed by an amine catalyzed allene–aldehyde tautomerization. Various substituted vinylogous aldehydes were prepared in one pot with good to excellent yields (up to 95%) under mild conditions with high atom economy.

  通过三唑-金（TA-Au）催化的炔丙基乙烯基醚重排，然后由胺催化的丙二烯-醛互变异构，开发了一种高效的取代共轭二烯合成方法。在温和的条件下以高原子经济性，在一个锅中制备各种取代的乙烯基醛，收率好至极好（高达95％）。
• Compounds and methods of treating ocular disorders
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US10363231B2

  公开（公告）日：2019-07-30

  A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

  一种治疗与眼组织中全反式视网膜增加有关的受试者眼部疾病的方法，包括向受试者施用治疗有效量的式（I）伯胺化合物及其药学上可接受的盐类。
• COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20170340581A1

  公开（公告）日：2017-11-30

  A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.
• [EN] COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT DE TROUBLES OCULAIRES
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2016085939A2

  公开（公告）日：2016-06-02

  A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.
• Controlling the Molecular Topology of Vinylogous Iminium Ions by Logical Substrate Design: Highly Regio- and Stereoselective Aminocatalytic 1,6-Addition to Linear 2,4-Dienals
  作者：Mattia Silvi、Indranil Chatterjee、Yiankai Liu、Paolo Melchiorre

  DOI：10.1002/anie.201305870

  日期：2013.10.4

  about topology control: The title reaction yields valuable tetrahydrofuran spirooxindoles (see scheme; TMS=trimethylsilyl), and exemplifies a rare asymmetric 1,6‐addition to linear 2,4‐dienals proceeding with high δ‐site‐ and stereoselectivity. A steering group at the β‐dienal position ensured molecular preorganization of the catalytically active vinylogous iminium ion intermediate for highly predictable

  有关拓扑控制的所有内容：标题反应可产生有价值的四氢呋喃螺硫醇（参见方案； TMS =三甲基甲硅烷基），并例举了罕见的不对称1,6加成反应，对线性2,4二烯进行高δ位和立体选择性的过程。β-二烯基位置上的一个转向基团确保了催化活性的乙烯基亚胺基离子中间体的分子预组织，从而可高度预测反应结果。