4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-carbaldehyde | 474779-14-1

• 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
• 英文名称: 4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-carbaldehyde
• 英文别名: 6-methyl-4,6-bis(4-methylpent-3-en-1-yl)cyclohexa-1,3-dienecarbaldehyde；6-methyl-4,6-bis(4-methylpent-3-enyl)cyclohexa-1,3-diene-1-carbaldehyde
• CAS: 474779-14-1
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: FENFKJSEQOAPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-carbaldehyde 在 lithium aluminium tetrahydride 作用下， 生成 [6-Methyl-4,6-bis-(4-methyl-pent-3-enyl)-cyclohexa-1,3-dienyl]-methanol
  参考文献：
  名称：

  柠檬醛及其相关反应的“醛醇缩合”

  摘要：

  柠檬醛与无水碱的反应最初导致环己-1,3-二烯甲醛。较强的碱和较长的反应时间导致与六氟环己-1,4-二烯-甲醛的共轭结合，以及六个碳原子的氧化损失，从而生成2-甲基-4-（4-甲基戊-3-烯基）苯甲醛。描述了柠檬醛和3-甲基-2-丁烯醛（=千里光醛）之间的混合羟醛反应。

  DOI：

  10.1002/hlca.19760590642
• 作为产物：
  描述：

  柠檬醛 在 氢氧化钾 作用下， 生成 4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-carbaldehyde
  参考文献：
  名称：

  柠檬醛及其相关反应的“醛醇缩合”

  摘要：

  柠檬醛与无水碱的反应最初导致环己-1,3-二烯甲醛。较强的碱和较长的反应时间导致与六氟环己-1,4-二烯-甲醛的共轭结合，以及六个碳原子的氧化损失，从而生成2-甲基-4-（4-甲基戊-3-烯基）苯甲醛。描述了柠檬醛和3-甲基-2-丁烯醛（=千里光醛）之间的混合羟醛反应。

  DOI：

  10.1002/hlca.19760590642

文献信息

• Substituted Cyclohexadienals - Syntheses and Applications
  申请人：Watanabe Coran M. H.

  公开号：US20070232813A1

  公开（公告）日：2007-10-04

  The present invention is generally directed to the use of L-proline and certain derivatives thereof to catalyze the asymmetric self-condensation of α,β-unsaturated aldehydes to form homodimer and heterodimer cyclohexadienals. Reaction conditions are mild and yet amenable to a variety of different substrates yielding molecules with complex scaffolds from simple precursors. This approach allows for diversification and synthesis of this structural class of compounds in sufficient quantity, purity and enantioselectivity for, e.g., biological investigations and use as fluorescent probes, anti-cancer agents, anti-bacterial agents, and/or anti-fungal agents. The present invention is also generally directed to the cyclohexadienals produced.

  本发明通常涉及利用L-脯氨酸及其某些衍生物催化α,β-不饱和醛进行不对称自缩合，形成同二聚体和杂二聚体环己二烯醛。反应条件温和，且适用于多种不同的底物，从简单的原料生成具有复杂支架的分子。这种方法允许以足够的数量、纯度和对映选择性多样化合成这类结构的化合物，例如用于生物学研究以及作为荧光探针、抗癌剂、抗菌剂和/或抗真菌剂。本发明还一般涉及所生产的环己二烯醛。
• Diastereoselective synthesis of chiral 1,3-cyclohexadienals
  作者：Aitor Urosa、Ignacio E. Tobal、Ángela P. de la Granja、M. Carmen Capitán、R. F. Moro、Isidro S. Marcos、Narciso M. Garrido、Francisca Sanz、Emilio Calle、David Díez

  DOI：10.1371/journal.pone.0192113

  日期：——

  with a chiral α,β-unsaturated aldehyde in the presence of a Jørgensen-Hayashi organocatalyst provides easy and stereocontrolled access to the cyclohexadienal backbone. This method allows for the synthesis of potential photoprotective chiral 1,3-cyclohexadienals and extra extended conjugation compounds in a simple manner.

  已经开发了生产手性1，3-环己二醛的新方法。在Jørgensen-Hayashi有机催化剂的存在下，不同的β-二取代-α，β-不饱和醛与手性α，β-不饱和醛的有机催化不对称反应可轻松且立体地控制环己二醛骨架。该方法允许以简单的方式合成潜在的光保护性手性1，3-环己二醛和额外的扩展共轭化合物。
• Synthesis of the Polycyclic Ring Systems of Artocarpol A and D
  作者：M. Peggy Paduraru、Peter D. Wilson

  DOI：10.1021/ol0360703

  日期：2003.12.1

  The first synthesis of the polycyclic ring systems of artocarpol A and D has been accomplished. These natural products were isolated recently from the root bark of Artocarpus rigida, and artocarpol A has been shown to have potent antiinflammatory properties. The synthesis of an artocarpol D analogue was achieved on condensation of 11H-dibenzo[b,f]oxepin-10-one with senecialdehyde. The reaction of this

  关节阿波罗A和D的多环系统的第一个合成已完成。这些天然产物最近是从硬皮面包树的根皮中分离出来的，并且已显示出木炭素A具有有效的抗炎特性。在11H-二苯并[b，f]氧杂环庚烷-10-酮与十二醛之间的缩合反应中，合成了腕果D类似物。该氧杂环丁酮与柠檬醛的反应提供了2H-吡喃，随后的辐照提供了类似的邻苯二酚A的反应。
• Intramolecular Aza-Diels-Alder Cyclization of a Dimerized Citral with Anilines Catalyzed by InCl₃
  作者：Yijang Chen、Mani Ramanathan、Shiuh-Tzung Liu

  DOI：10.1002/jccs.201500112

  日期：2015.9

  series of aza‐polycyles containing octahydroacridine core were prepared via an intramolecular aza‐Diels‐Alder reaction of a dimerized citral with various aromatic amines. This reaction is efficiently catalyzed by InCl3 at ambient temperature to afford the corresponding cyclized products in moderate to good yields.

  通过二聚柠檬酸与各种芳族胺的分子内氮杂-Diels-Alder反应制备了一系列含八氢ac啶核的氮杂多环。该反应在环境温度下被InCl 3有效催化，以中等至良好的产率得到相应的环化产物。
• The proline and β-lactoglobulin mediated asymmetric self-condensation of β-ionylideneacetaldehyde, retinal and related compounds.
  作者：Alfred E. Asato、Coran Watanabe、Xiao-Yuan Li、R.S.H. Liu

  DOI：10.1016/s0040-4039(00)79825-x

  日期：1992.5

  Proline was found to effectively mediate the asymmetric reaction of beta-ionylideneacetaldehyde 1A, retinal and related alpha,beta-unsaturated aldehydes to form their corresponding self-condensation products in reasonable enantiomeric excess (up to 65% ee). This same interesting conversion was also observed when 1A was incubated in the presence of the milk whey protein beta-lactoglobulin (BLG).