4-(9H-fluoren-2-yl)-6-(4-nitrophenyl)cyclohexa-1,3-dienecarbaldehyde | 951772-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(9H-fluoren-2-yl)-6-(4-nitrophenyl)cyclohexa-1,3-dienecarbaldehyde
• 英文别名: 4-(9H-fluoren-2-yl)-6-(4-nitrophenyl)cyclohexa-1,3-diene-1-carbaldehyde
• CAS: 951772-79-5
• 化学式: C₂₆H₁₉NO₃
• 分子量: 393.442
• InChiKey: XHWREFFKEPYUOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(9H-fluoren-2-yl)-but-2-enal 、 对硝基肉桂醛 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以22%的产率得到4-(9H-fluoren-2-yl)-6-(4-nitrophenyl)cyclohexa-1,3-dienecarbaldehyde
  参考文献：
  名称：

  Synthesis and cellular effects of cycloterpenals: Cyclohexadienal-based activators of neurite outgrowth

  摘要：

  An unusual class of diterpenoid natural products, 'cycloterpenals' ( with a central cyclohexadienal core), that arise in nature by condensation of retinoids and other isoprenes, have been isolated from a variety of organisms including marine sponges as well as from the human eye. A milk whey protein has also demonstrated the formation of a cycloterpenal derived from beta-ionylidineacetaldehyde. Here, we generate a synthetic library of these molecules where we detail reaction conditions required to effect cross condensation of alpha,beta-unsaturated aldehydes as opposed to homodimerization. The ability of this class of molecules to activate neurite outgrowth activity is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.030

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。
• Synthesis and cellular effects of cycloterpenals: Cyclohexadienal-based activators of neurite outgrowth
  作者：Bennie J. Bench、Shane E. Tichy、Lisa M. Perez、Jenna Benson、Coran M.H. Watanabe

  DOI：10.1016/j.bmc.2008.07.030

  日期：2008.8

  An unusual class of diterpenoid natural products, 'cycloterpenals' ( with a central cyclohexadienal core), that arise in nature by condensation of retinoids and other isoprenes, have been isolated from a variety of organisms including marine sponges as well as from the human eye. A milk whey protein has also demonstrated the formation of a cycloterpenal derived from beta-ionylidineacetaldehyde. Here, we generate a synthetic library of these molecules where we detail reaction conditions required to effect cross condensation of alpha,beta-unsaturated aldehydes as opposed to homodimerization. The ability of this class of molecules to activate neurite outgrowth activity is reported. (C) 2008 Elsevier Ltd. All rights reserved.