2,5-Dipiperonyliden-cyclopentanon-(1) | 5447-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2,5-Dipiperonyliden-cyclopentanon-(1)
• 英文别名: 2,5-bis((benzo[d][1,3]dioxol-5-yl)methylene)cyclopentanone；2,5-dipiperonylidene-cyclopentanone；2,5-Dipiperonyliden-cyclopentanon；2,5-Bis(1,3-benzodioxol-5-ylmethylidene)cyclopentan-1-one
• CAS: 5447-52-9
• 化学式: C₂₁H₁₆O₅
• 分子量: 348.355
• InChiKey: LNKNETAYXQLOBY-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C(Solv: ethanol (64-17-5))
• 沸点：
  572.5±50.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-Dipiperonyliden-cyclopentanon-(1) 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99 %的产率得到(2S,5S)-2,5-bis(benzo[d][1,3]dioxol-5-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：

  胡椒醛 、 环戊酮 在 ash of pomegranate peels 作用下， 以 水 为溶剂， 反应 0.42h， 以76%的产率得到2,5-Dipiperonyliden-cyclopentanon-(1)
  参考文献：
  名称：

  石榴皮灰（APP）：一种生物废物多相催化剂，用于可持续合成α，α'-双（取代苄基）环烷酮和2-芳基-1-丁酮

  摘要：

  摘要 以石榴皮（APP）的灰分为催化剂，由水中的各种取代的醛和环烷酮可高效制备α，α'-双（取代的亚苄基）环烷酮。通过简单的热处理将石榴果皮干燥即可从生物废料中获得APP催化剂，并通过FT-IR，XRD，XRF，EDX，SEM，DSC-TGA和BET技术证实了其活性相的形成。分析表明，本发明的催化剂具有促进所需产物合成的碱性位点。我们协议的主要吸引力是利用高度丰富的生物废物衍生催化剂，并在最短的反应时间内获得良好至优异的产率。通过在低温下将等摩尔量的芳族醛和1-四氢萘酮缩合，该绿色方案进一步扩展为结构上多样化的2-亚芳基-1-四氢萘酮。 图形摘要

  DOI：

  10.1007/s11164-020-04160-5

文献信息

• Synthesis and Fluorescence Properties of α,α′-Bis(substituted-benzylidene)cycloalkanones Catalyzed by 1-Methyl-3(2-(sulfooxy)ethyl)-1<i>H</i>-imidazol-3-ium Chloride
  作者：Yu Wan、Xiu-Mei Chen、Li-Ling Pang、Rui Ma、Cai-Hui Yue、Rui Yuan、Wei Lin、Wei Yin、Rong-Cheng Bo、Hui Wu

  DOI：10.1080/00397910903243781

  日期：2010.7.12

  α,α′-Bis(substituted-benzylidene)cycloalkanones were synthesized via a solvent-free cross-aldol condensation of aromatic aldehydes with cycloalkanones in the presence of a catalytic amount 1-methyl-3(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride at room temperature with excellent yields. The screening for optical properties indicated that the size of cycloalkanone has an influence on the fluorescence

  在催化量的 1-甲基-3(2-(磺氧基)乙基)-1H 存在下，通过芳香醛与环烷酮的无溶剂交叉羟醛缩合反应合成了 α,α'-双（取代亚苄基）环烷酮-咪唑-3-氯化鎓在室温下以优异的收率。光学性质的筛选表明，环烷酮的大小对产物的荧光发射有影响。来自环己酮的产物比来自环戊酮的产物具有更强的荧光发射。
• Pal, Rammohan; Mandal, Tapas K.; Guha, Chayan, Journal of the Indian Chemical Society, 2011, vol. 88, # 5, p. 711 - 717
  作者：Pal, Rammohan、Mandal, Tapas K.、Guha, Chayan、Mallik, Asok K.

  DOI：——

  日期：——
• Wallach, Chemisches Zentralblatt, 1908, vol. 79, # I, p. 637,639
  作者：Wallach

  DOI：——

  日期：——
• Mentzel, Chemische Berichte, 1903, vol. 36, p. 1502
  作者：Mentzel

  DOI：——

  日期：——
• 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.