(E)-2-(3-fluorobenzylidene)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(3-fluorobenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: E-2-(3'-fluorobenzylidene)-1-indanone；2-(3-Fluorophenylmethylene)-1-indanone；(2E)-2-[(3-fluorophenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₆H₁₁FO
• 分子量: 238.261
• InChiKey: JMCDWSXNAOUYOU-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-isothiocyanatooxindole 、 (E)-2-(3-fluorobenzylidene)-2,3-dihydro-1H-inden-1-one 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  3-异硫氰酸酯基羟吲哚与环外α，β不饱和酮的对映选择性催化级联迈克尔/环化反应途中到-3,2'-吡咯烷基bispirooxindoles †

  摘要：

  研究表明，在存在奎宁衍生的叔氨基-方酸酰胺催化剂的情况下，3-异硫氰酸根合吲哚与环外α，β-不饱和酮之间的级联迈克尔/环化反应可以有效地进行，并提供包含两个螺-季四元的3,2'-吡咯烷基二螺氧基辛多烯和三个连续的立体中心，作为单一的非对映异构体，具有出色的对映选择性（最高99：1 er）。

  DOI：

  10.1039/c6ob02187e
• 作为产物：
  描述：

  1-茚酮 、 3-氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以48%的产率得到(E)-2-(3-fluorobenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  设计，合成和结构与活性关系的研究含卤素的2-亚苄基-1-茚满酮衍生物，用于抑制脂多糖刺激的RAW 264.7巨噬细胞中的ROS产生。

  摘要：

  为了不断发现新的潜在抗炎药，我们系统地设计和合成了具有查耳酮结构修饰的61个2-亚苄基-1-茚满酮衍生物，并评估了其对RAW 264.7巨噬细胞中LPS刺激的ROS产生的抑制活性。 。系统的结构-活性关系研究表明，茚满酮部分的C-5，C-6或C-7位置具有羟基，苯环的邻氟，间氟或对氟，三氟甲基，三氟甲氧基和溴官能团在抑制LPS刺激的RAW 264.7巨噬细胞中ROS的产生中起重要作用。在所有测试的化合物中，6-羟基-2-（2-（三氟甲氧基）亚苄基）-2,3-二氢-1H-茚满-1-一（化合物44）对ROS产生最强的抑制活性。对作用方式的进一步研究表明，化合物44通过调节NADPH氧化酶有效抑制LPS刺激的ROS产生。这项工作的发现可能有助于设计基于2-亚苄基-茚满酮的先导化合物作为新型抗炎药。

  DOI：

  10.1016/j.ejmech.2017.03.049

文献信息

• Domino reactions in water for the stereoselective synthesis of novel spiro dihydro-2′H-[indene-2,3′-thiophen]-1(3H)-ones with three contiguous stereocenters
  作者：Sundaravel Vivek Kumar、Pitchaimani Prasanna、Subbu Perumal

  DOI：10.1016/j.tetlet.2013.09.123

  日期：2013.11

  triethylamine in water stereoselectively afforded a library of 2′-(aryl)-4′-hydroxy-4′,5′-dihydro-2′H-spiro[indene-2,3′-thiophen]-1(3H)-ones. This transformation presumably proceeds via the generation of 2-mercaptoacetaldehyde from 1,4-dithiane-2,5-diol followed by Michael addition–intramolecular aldol sequence with C–C and C–S bond formations and creation of three contiguous stereocenters in a one-pot operation

  在三乙胺的存在下，（E）-2-（芳基）-2,3-二氢-1 H-茚满-1-酮与1,4-二噻吩-2,5-二醇的多米诺反应立体选择性地得到的2库' - （芳基）-4'-羟基-4'，5'-二氢-2' ħ -螺[茚-2,3'-噻吩] -1（3 ħ） -酮。这种转变大概是通过从1,4-二噻二-2,5-二醇生成2-巯基乙醛，然后通过迈克尔加成-具有C-C和C-S键形成的分子内羟醛序列，以及在一个环中形成三个连续的立体中心而进行的。锅操作。
• Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease
  作者：Tara Man Kadayat、Suhrid Banskota、Pallavi Gurung、Ganesh Bist、Til Bahadur Thapa Magar、Aarajana Shrestha、Jung-Ae Kim、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2017.06.018

  日期：2017.9

  To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1-Hinden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-alpha-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-alpha-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-kappa B transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-alpha gene, with compound 55 showing better efficacy. This inhibition of TNF-alpha expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-alpha expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD. (C) 2017 Elsevier Masson SAS. All rights reserved.
• E -2-Benzylidenebenzocycloalkanones. Stereostructure and NMR spectroscopic investigation
  作者：P. Perjési、T. Nusser、Gy. Tarczay、P. Sohár

  DOI：10.1016/s0022-2860(98)00805-9

  日期：1999.4

  Series of E-2-benzylideneindanones (a), -tetralones (b) and -benzosuberones (c) with OCH(3) (2-4), NO(2) (5-7) and F (8-10) substitutions (ortho, meta and par-a) on their benzylidene moiety were synthesized by aldol condensation of the appropriate aldehydes and benzocyclanones. The stereostructure (configuration and conformation) and the electronic properties (conjugation of the enone moiety with the aromatic rings) of the compounds were studied by IR, (1)H and (13)C NMR spectroscopy including also 2D-HSC, DNOE and DEPT measurements. Ab initio calculations were carried out to corroborate the experimental findings. (C) 1999 Elsevier Science B.V. All rights reserved.