4-(6'-hydroxyhexyl)benzaldehyde | 143745-44-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(6'-hydroxyhexyl)benzaldehyde
• 英文别名: 4-(6-Hydroxyhexyl)benzaldehyde
• CAS: 143745-44-2
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: CJSYUJMQBMWXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(6'-hydroxyhexyl)benzaldehyde 在 咪唑 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 甲基磺酰氯 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 4-{6'-[(tert-butyldimethylsilyl)oxy]hexyl}benzyl chloride
  参考文献：
  名称：

  对映选择性SmI 2介导的醛与对位异构体1-萘酰胺巴豆酸酯的还原性偶联中的有效远程轴对中心手性转移。

  摘要：

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。

  DOI：

  10.1021/jo0526486
• 作为产物：
  描述：

  4-(6'-hydroxyhex-1-ynyl)benzaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 2.0h， 以70%的产率得到4-(6'-hydroxyhexyl)benzaldehyde
  参考文献：
  名称：

  对映选择性SmI 2介导的醛与对位异构体1-萘酰胺巴豆酸酯的还原性偶联中的有效远程轴对中心手性转移。

  摘要：

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。

  DOI：

  10.1021/jo0526486

文献信息

• Synthesis of chlorophyll-BODIPY conjugates and their intramolecular excitation energy transfer
  作者：Yuna Mori、Yugo Nakamura、Mizuki Yasui、Hitoshi Tamiaki

  DOI：10.1142/s1088424623501225

  日期：2024.1

  Zinc 3-hydroxymethyl-pyropheophorbides-[Formula: see text] covalently linked with an 8-aryl-1,3,5,7-tetramethyl-BODIPY moiety in the 17-substituent were synthesized by chemically modifying naturally occurring chlorophyll(Chl)-[Formula: see text]. The synthetic Chl–BODIPY conjugates in tetrahydrofuran exhibited sharp visible absorption and weak circular dichroism spectra, indicating that their molecules were fully dispersed in the solution. In their ground states, no intramolecular interaction between the Chl and BODIPY parts was observed. By contrast, singlet excitation energy was efficiently transferred from the photoexcited BODIPY moiety to zinc chlorin moiety within their molecules. The intramolecular energy transfer efficiencies exceeded 90% and were independent of the linkages including ester and amide bonds as well as methylene and hexamethylene spacers.

  通过化学修饰天然叶绿素（Chl）-[式：见正文]，合成了在 17-取代基中与 8-芳基-1,3,5,7-四甲基-BODIPY 共价连接的 3-羟甲基-pyropheophorbides-锌[式：见正文]。合成的 Chl-BODIPY 共轭物在四氢呋喃中显示出锐利的可见吸收光谱和微弱的圆二色光谱，表明其分子完全分散在溶液中。在它们的基态中，没有观察到 Chl 和 BODIPY 部分之间的分子内相互作用。相反，在它们的分子中，单色激发能量从光激发的 BODIPY 分子有效地转移到了氯素锌分子中。分子内能量传递效率超过 90%，并且与酯键和酰胺键以及亚甲基和六亚甲基间隔物等连接方式无关。
• Synthesis and spectral properties of fluorescent linear alkylphosphocholines labeled with all-(E)-1,6-diphenyl-1,3,5-hexatriene
  作者：Valentín Hornillos、Laura Tormo、Francisco Amat-Guerri、A. Ulises Acuña

  DOI：10.1016/j.jphotochem.2010.09.010

  日期：2010.11

  A synthetic method has been designed to produce alkylphosphantidylcholine lipid molecules with the fluorescent group all-(E)-1 6-diphenyl-1 3 5-hexatriene (DPH) incorporated to the end of a polymethylene chain of variable length The resulting compounds may be viewed as single-chain fluorescent lipid probes terminated with a phosphocholine (PHC) polar head-group The method was applied to the synthesis of two lipids with different alkyl chain length PHC-C4-DPH (1) and PHC-C6-DPH (2) as well as the corresponding alcohols OH-C4-DPH (8) and OH-C6-DPH (9) The absorption and fluorescence properties of these compounds in fluid solution were very similar to those of the well-known lipid probe propionic acid-DPH (PA-DPH) In addition it was observed that the alkylphosphocholines were easily incorporated into unilamellar lipid vesicles in which the DPH group would be positioned most likely near the centre of the bilayer In these conditions 1 shows a fluorescence quantum yield of 0 4 +/- 0 1 and a relatively simple decay time with tau(av), close to 5 0 ns Fluorescence polarization experiments also indicate that the reorientational motions of the DPH group of phosphocholine 1 are sensitive to the fluidity changes that accompany the main thermal phase transition of the bilayer As a result both compounds may be of utility as novel fluorescent lipid probes characterized by a biomimetic zwitterionic polar head-group (C) 2010 Elsevier B V All rights reserved
• Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI₂-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
  作者：Yan Zhang、Yongqiang Wang、Wei-Min Dai

  DOI：10.1021/jo0526486

  日期：2006.3.1

  different 2-substituted 8-methoxy-1-naphthamides. The enantiomers of atropisomeric 8-methoxy-1-naphthamides were prepared through a chemical resolution process, and their absolute stereochemistry was determined by X-ray crystal structural analysis. It was found that the linkage between crotonate and the C2 position of 8-methoxy-1-naphthamides remarkably influenced the efficiency of remote chirality transfer

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。