2,5-bis (3-methoxybenzylidene)cyclopentanone | 111162-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis (3-methoxybenzylidene)cyclopentanone
• 英文别名: 2,5-Bis[(3-methoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 111162-93-7
• 化学式: C₂₁H₂₀O₃
• mdl: MFCD03415212
• 分子量: 320.388
• InChiKey: PVJQLZZXRRBHRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三溴甲烷 、 2,5-bis (3-methoxybenzylidene)cyclopentanone 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以65%的产率得到(E)-1,1-dibromo-5-(3-methoxybenzylidene)-2-(3-methoxyphenyl)-spiro[2.4]heptan-4-one
  参考文献：
  名称：

  镁介导的溴仿与缺电子烯烃共轭加成中的底物定向选择性。

  摘要：

  已经研究了镁介导的溴仿与多种缺电子烯烃的共轭加成。在硝基二烯和二亚苄基丙酮的情况下，分离出三溴甲基化产物，而用环状二亚苄基酮和 3-烯烃羟吲哚得到螺环丙烷化产物。由环状二亚苄基酮衍生的螺环丙基酮通过Cloke-Wilson 重排成功地转化为稠合呋喃。

  DOI：

  10.1039/d0ob00599a
• 作为产物：
  描述：

  环戊酮 、 3-甲氧基苯甲醛 在 五氯化钼 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以99%的产率得到2,5-bis (3-methoxybenzylidene)cyclopentanone
  参考文献：
  名称：

  通过无溶剂微波辅助的绿色，快速，高效合成α，α'-双[（芳基或烯丙基）亚烷基]环烷酮和2-[[（芳基或烯丙基）亚烷基] -1-茚满酮作为潜在的生物化合物MoCl5催化的克莱森-施密特缩合反应

  摘要：

  一种新的，绿色的，高效的方法，可通过简单的微波快速制备某些α，α'-双[（芳基或烯丙基）亚烷基]环烷酮和2 [[（芳基或烯丙基）亚烷基] -1-茚满酮MoCl 5催化的克莱森-施密特辅助缩合反应开发成功。当前方法的突出特点包括：使用无溶剂条件，操作简单，使用非常便宜和可用的催化剂，催化剂用量低，反应时间短，纯产物的收率高，无有害副产物，易于后处理以及微波辐射作为清洁能源的适用性。此外，成功进行了克级反应，证明了当前Claisen-Schmidt缩合反应的可扩展性。

  DOI：

  10.1002/jccs.201900081

文献信息

• Fast, Facile and Convenient Synthesis of<i>α,α</i>-Bis(substituted-arylidene) Cycloalkanones: An improved Protocol
  作者：Gholam Hossein Mahdavinia、Maryam Mirzazadeh

  DOI：10.1155/2012/390528

  日期：——

  Commercially available potassium hydroxide (KOH), a simple base, was found to be a catalyst for tandem cross-aldol condensation between cyclic ketones and aromatic aldehydes leading to a fast and easy synthesis ofα,α-bis (substituted-arylidene) cycloalkanones in the shortest times of all previous methods. The reaction of aryl aldehydes with five and six-membered cyclic ketones afforded excellent yields after few seconds in most cases. The reaction conditions were compatible with various electron withdrawing and electron donating substituents,e.g.Cl, F, NO₂, OMe, Me and NMe₂.

  商业上可获得的氢氧化钾（KOH），一种简单的碱，被发现是环状酮和芳香醛之间串联十字-醛缩合的催化剂，从而在所有先前方法中时间最短地合成α,α-双（取代芳基亚亚甲基）环戊酮。芳基醛与五元和六元环状酮的反应在大多数情况下在几秒钟后得到了优异的产率。反应条件与各种电子吸引和电子供体取代基兼容，e.g.Cl，F，NO₂，OMe，Me和NMe₂。
• Efficient One-Pot Synthesis of Some New Xanthene Derivatives Based on the Reaction of Dimedone with α,α′-Bis(substituted-benzylidene) Cycloalkanones Using Catalytic Amount of_pTSA
  作者：Zahed Karimi-Jaberi、Baharak Pooladian

  DOI：10.1080/00397911.2011.627104

  日期：2013.4.18

  Abstract GRAPHICAL ABSTRACT

  摘要图形抽象
• Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway
  作者：Pay-Chin Leow、Priti Bahety、Choon Pei Boon、Chong Yew Lee、Kheng Lin Tan、Tianming Yang、Pui-Lai Rachel Ee

  DOI：10.1016/j.ejmech.2013.10.073

  日期：2014.1

  Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/beta-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of beta-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of beta-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than la (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Ajani, Olayinka Oyewale; Ituen, Ruth Itoroabasi; Falomo, Ayorinde, Pakistan Journal of Scientific and Industrial Research, 2011, vol. 54, # 2, p. 59 - 67
  作者：Ajani, Olayinka Oyewale、Ituen, Ruth Itoroabasi、Falomo, Ayorinde

  DOI：——

  日期：——
• Green, rapid, and highly efficient syntheses of <i>α</i> , <i>α′</i> ‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones as potentially biologic compounds via solvent‐free microwave‐assisted Claisen–Schmidt condensation catalyzed by MoCl ₅
  作者：Reza Bakhshi、Behzad Zeynizadeh、Hossein Mousavi

  DOI：10.1002/jccs.201900081

  日期：2020.4

  A new, green, and highly efficient protocol for the expeditious preparation of some α,α′‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones via a simple microwave‐assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent‐free conditions, simple operation, use of

  一种新的，绿色的，高效的方法，可通过简单的微波快速制备某些α，α'-双[（芳基或烯丙基）亚烷基]环烷酮和2 [[（芳基或烯丙基）亚烷基] -1-茚满酮MoCl 5催化的克莱森-施密特辅助缩合反应开发成功。当前方法的突出特点包括：使用无溶剂条件，操作简单，使用非常便宜和可用的催化剂，催化剂用量低，反应时间短，纯产物的收率高，无有害副产物，易于后处理以及微波辐射作为清洁能源的适用性。此外，成功进行了克级反应，证明了当前Claisen-Schmidt缩合反应的可扩展性。