1,5-bis(naphthalen-2-yl)penta-1,4-dien-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis(naphthalen-2-yl)penta-1,4-dien-3-one
• 英文别名: 2,5-Bis(naphthalen-2-ylmethylidene)cyclopentan-1-one
• 化学式: C₂₇H₂₀O
• 分子量: 360.455
• InChiKey: RECLYTIMHFKAFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1,5-bis(naphthalen-2-yl)penta-1,4-dien-3-one 在 氢气 、 C₃₇H₃₆IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 作用下， 以 邻二甲苯 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 以98 %的产率得到(2S,5S)-2,5-bis(naphthalen-2-ylmethyl)cyclopentan-1-one
  参考文献：
  名称：

  铱催化2,5-二亚烷基环戊酮双不对称氢化合成手性环戊酮

  摘要：

  在此，我们报道了一种有效的铱催化双不对称氢化 2,5-二亚烷基环戊酮，以优异的收率和立体选择性提供手性 2,5-二取代环戊酮。动力学实验和对照实验的结果表明，两个C=C键是逐步加氢的，第二个立体中心是由手性催化剂和单加氢产物的手性协同控制的。氢化产物可以以克级制备并且易于衍生化。

  DOI：

  10.1021/acs.orglett.2c02656
• 作为产物：
  描述：

  环戊醇 、 2-萘甲醛 在 potassium carbonate 作用下， 以72%的产率得到1,5-bis(naphthalen-2-yl)penta-1,4-dien-3-one
  参考文献：
  名称：

  碱催化的仲醇和芳基醛的交叉偶联，同时伴随醇的氧化为酮：合成Claisen-Schmidt缩合产物的另一种方法

  摘要：

  当在催化量（20摩尔％）的K 2 CO存在下，将芳基醛的醇溶液回流搅拌45小时时，实现了碱催化的仲醇与芳基醛的CC交叉偶联3。使用各种仲醇和取代的芳基醛，可以以中等至良好的收率获得一致形成的α，α'-双-（亚苄基）链烷酮。在此，已经通过使用仲醇的替代策略合成了作为克莱森-施密特（十字醇醛）缩合的经典产物的α，α′-双-（亚苄基）链烷酮。双-（亚苄基）链烷酮是各种药物方案和双酚生产中必不可少的部分不使用任何贵金属的-（亚苄基）链烷酮是本反应的主要结果。

  DOI：

  10.1016/j.tetlet.2017.05.093

文献信息

• Sulfuric Acid-modified PEG-6000 (PEG-SO<sub>3</sub>H): An Efficient, Bio-degradable and Reusable Catalyst for Synthesis of α, α' bis(arylidene) Cycloalkanones Under Solvent-free Conditions
  作者：Mohammad A. Nasseri、Mehri Salimi

  DOI：10.2174/1570178611310030004

  日期：2013.4.1

  A green and efficient method for synthesis of α,α'  -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical

  一种绿色高效的合成α，α'??的方法 描述了一种双（亚芳基）环烷酮，它是在80℃无溶剂条件下，使用磺化聚乙二醇6000（PEG-SO 3 H）作为稳定，可重复使用和可生物降解的催化剂，从芳族醛与酮反应制得的。使用无毒，便宜，易于获得和可回收的催化剂使该方案切实可行，对环境友好并且在经济上具有吸引力。
• The Syntheses of New Cyclopenta[d][1,3]thiazine Derivatives and Their Use as Antimicrobial Agents
  作者：M. S. A. El-Gaby、N. M. Saleh、J. A. Micky、Y. A. Ammar、H. S. A. Mohamed

  DOI：10.1080/10426500500366947

  日期：2006.6.1

  Cyclopentanone (1) was exploited as a starting material for the syntheses of hitherto unknown cyclopenta[d][1,3]thiazine derivatives.

  环戊酮 (1) 被用作合成迄今为止未知的环戊二烯 [d][1,3] 噻嗪衍生物的起始材料。
• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.
• Base-catalyzed cross coupling of secondary alcohols and aryl-aldehydes with concomitant oxidation of alcohols to ketones: An alternative route for synthesis of the Claisen-Schmidt condensation products
  作者：Naveen Satrawala、Kamal N. Sharma、Leah C. Matsinha、Latisa Maqeda、Shepherd Siangwata、Gregory S. Smith、Raj K. Joshi

  DOI：10.1016/j.tetlet.2017.05.093

  日期：2017.7

  alkanones was obtained in moderate to good yields using various secondary alcohols and substituted aryl-aldehydes. Herein, α,α′-bis-(benzylidene)alkanones, which are the classical products of Claisen-Schmidt (cross aldol) condensation, have been synthesized via an alternative strategy using secondary alcohols. Bis-(benzylidene) alkanones are an integral part of various drug regimes and the production of bis-(benzylidene)

  当在催化量（20摩尔％）的K 2 CO存在下，将芳基醛的醇溶液回流搅拌45小时时，实现了碱催化的仲醇与芳基醛的CC交叉偶联3。使用各种仲醇和取代的芳基醛，可以以中等至良好的收率获得一致形成的α，α'-双-（亚苄基）链烷酮。在此，已经通过使用仲醇的替代策略合成了作为克莱森-施密特（十字醇醛）缩合的经典产物的α，α′-双-（亚苄基）链烷酮。双-（亚苄基）链烷酮是各种药物方案和双酚生产中必不可少的部分不使用任何贵金属的-（亚苄基）链烷酮是本反应的主要结果。
• Iridium-Catalyzed Double Asymmetric Hydrogenation of 2,5-Dialkylienecyclopentanones for the Synthesis of Chiral Cyclopentanones
  作者：Yu Nie、Qianjia Yuan、Feng Gao、Masahiro Terada、Wanbin Zhang

  DOI：10.1021/acs.orglett.2c02656

  日期：2022.11.4

  Herein, we report an efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones, delivering the chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results of the kinetic experiments and control experiments indicated that the two C═C bonds were hydrogenated in a stepwise manner and the second stereocenter was synergistically controlled

  在此，我们报道了一种有效的铱催化双不对称氢化 2,5-二亚烷基环戊酮，以优异的收率和立体选择性提供手性 2,5-二取代环戊酮。动力学实验和对照实验的结果表明，两个C=C键是逐步加氢的，第二个立体中心是由手性催化剂和单加氢产物的手性协同控制的。氢化产物可以以克级制备并且易于衍生化。