(E)-2-(3,4-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one | 130689-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-2-(3,4-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-(3,4-Dimethoxybenzyliden)-1-tetralon；2-(3,4-Dimethoxy benzylidene)-1-tetralone；(2E)-2-[(3,4-dimethoxyphenyl)methylidene]-3,4-dihydronaphthalen-1-one
• CAS: 130689-14-4
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: GAWLBBIQPOSEMR-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-2-(3,4-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one 在 氯化(均三甲苯)[(R,R)-N-(对甲苯磺酰基)-1,2-二苯乙烯基二胺]钌(II) 、 十六烷基三甲基溴化铵 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium formate 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 72.25h， 以59%的产率得到(1R,2S)-2-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Noyori–Ikariya Ru（II）配合物催化亚芳基取代的色酮和四酮的不对称转移加氢：一键还原C═C和C═O键

  摘要：

  在2和3的存在下，通过C andC和C oneO一锅还原，将3-Arylidenechroman-4-ones和2-芳基-1-四氢萘酮在dr和er中以高达99：1的比例氢化为顺式苄醇。在不对称转移氢化动力学动力学拆分（ATH-DKR）条件下，Noyori–Ikariya型Ru II手性配合物和HCO 2 Na的含量为5 mol％。这些底物的氧化导致天然高纯异黄烷酮二氢bonducellin及其碳水化合物类似物的对映选择性合成。

  DOI：

  10.1021/acs.joc.0c02981
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 3,4-二氢-1(2H)-萘酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以62%的产率得到(E)-2-(3,4-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Noyori–Ikariya Ru（II）配合物催化亚芳基取代的色酮和四酮的不对称转移加氢：一键还原C═C和C═O键

  摘要：

  在2和3的存在下，通过C andC和C oneO一锅还原，将3-Arylidenechroman-4-ones和2-芳基-1-四氢萘酮在dr和er中以高达99：1的比例氢化为顺式苄醇。在不对称转移氢化动力学动力学拆分（ATH-DKR）条件下，Noyori–Ikariya型Ru II手性配合物和HCO 2 Na的含量为5 mol％。这些底物的氧化导致天然高纯异黄烷酮二氢bonducellin及其碳水化合物类似物的对映选择性合成。

  DOI：

  10.1021/acs.joc.0c02981

文献信息

• Intermolecular Reductive Cyclodimerization of Cyclic α,β-Unsaturated Ketones­ Promoted by a Low-Valent Titanium Reagent: A Facile Synthesis of Some New Spiro Compounds
  作者：Da-Qing Shi、Guo-Lan Dou、Zheng-Yi Li、Chun-Ling Shi、Xiao-Yue Li、Hong Jiang、Sai-Nan Ni、Shun-Jun Ji

  DOI：10.1055/s-2007-983707

  日期：2007.6

  β-unsaturated ketones such as 2-benzylideneindan-1-ones, 2-benzylidene-1 -tetralones, 3-benzylidenechroman-4-ones, and 3-benzylidenethiochroman-4-ones induced by a low-valent titanium reagent were studied. Some new spiro compounds were prepared in good yields under neutral and mild conditions. High stereoselectivity was achieved and the stereochemistry of the products was confirmed by X-ray diffraction

  α,β-不饱和酮如 2-benzylideneindan-1-ones、2-benzylidene-1-tetralones、3-benzylidenechroman-4-ones 和 3-benzylidenethiochroman-4-ones 的分子间还原环二聚反应对低价钛试剂进行了研究。一些新的螺环化合物在中性和温和条件下以高收率制备。实现了高立体选择性，并通过 X 射线衍射分析证实了产物的立体化学。
• Synthesis of Trans- and<i>cis</i>-2-acetyl-3-phenyl-3,3a,4,5-tetrahydro-2<i>H</i>-benzo[<i>g</i>] Indazoles: Evaluation as Inhibitors of β-hematin Formation
  作者：Daniel A. Aparicio、Gricela M. Lobo、Jennifer L. Sánchez、Melina C. Monasterios、María E. Acosta、Lola De Lima、Ligia J. Llovera、Jorge E. Ángel、Jaime E. Charris

  DOI：10.3184/174751917x15105690662845

  日期：2017.11

  Several trans- and cis-2-acetyl-3-(substituted-phenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole derivatives have been synthesised via the condensation of the appropriate exocyclic α,β-unsaturated ketones with hydrazine in hot acetic acid, to obtain diastereomeric mixtures of N-acetylated isomers. Structure elucidation was based on their spectral data and the trans–cis stereochemistry using of NOE and

  通过适当的环外α,β-缩合合成了几种反式和顺式-2-乙酰基-3-(取代-苯基)-3,3a,4,5-四氢-2H-苯并[g]吲唑衍生物不饱和酮与肼在热乙酸中反应，得到 N-乙酰化异构体的非对映混合物。结构解析基于它们的光谱数据和使用 NOE 和 NOESY 实验的反式-顺式立体化学。对这些衍生物作为β-血红素形成抑制剂进行了生物学测试。
• Pharmaceutical compounds
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0618206A1

  公开（公告）日：1994-10-05

  The invention provides pharmaceutical compounds of the formula: in which A --- B is CH₂-CH₂ or CH=CH; X is a pyridine or benzene ring; when X is pyridine n is 0; when X is benzene n is 0, 1 or 2 and when A --- B is CH₂-CH₂, R¹ is attached at any of the positions 7 to 10, and when A --- B is CH=CH, R¹ is attached at any of the positions 5 to 10; each R¹ is halo, carboxy, trifluoromethyl, hydroxy, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ alkylthio, hydroxy-C₁₋₄ alkyl, hydroxy-C₁₋₄ alkoxy, nitrogen-containing heterocyclyl, nitro, trifluoromethoxy, -COOR⁵ where R⁵ is an ester group, -COR⁶, -CONR⁶R⁷ or -NR⁶R⁷ where R⁶ and R⁷ are each hydrogen or C₁₋₄ alkyl; R² is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R² is furanyl optionally substituted with C₁₋₄ alkyl; R³ is nitrile, carboxy, -COOR⁸ where R⁸ is an ester group, -CONR⁹R¹⁰ where R⁹ and R¹⁰ are each hydrogen or C₁₋₄ alkyl, or -SO₂R¹¹ where R¹¹ is C₁₋₄ alkyl, optionally substituted phenyl or optionally substituted phenyl-C₁₋₄ alkyl; and R⁴ is 1-pyrrolyl, 1-imidazolyl or 1-pyrazolyl, said 1-pyrrolyl, 1-imidazolyl and 1-pyrazolyl being optionally substituted by one or two C₁₋₄ alkyl, carboxyl, hydroxy-C₁₋₄ alkyl or -CHO groups, or 1-(1,2,4-triazolyl), 1-(1,3,4-triazolyl) or 2-(1,2,3-triazolyl), said triazolyl groups being optionally substituted by a C₁₋₄ alkyl or C₁₋₄ perfluoroalkyl group, or 1-tetrazolyl optionally substituted by C₁₋₄ alkyl; and salts thereof.

  本发明提供了式中的药物化合物： 其中 A --- B 是 CH₂-CH₂ 或 CH=CH； X 是吡啶或苯环； 当 X 为吡啶时 n 为 0； 当X为苯时，n为0、1或2；当A--B为CH₂-CH₂时，R¹连接在7至10的任一位置；当A--B为CH＝CH时，R¹连接在5至10的任一位置； 每个 R¹ 是卤代、羧基、三氟甲基、羟基、C₁₋₄ 烷基、C₁₋₄ 烷氧基、C₁₋₄ 烷硫基、羟基-C₁₋₄ 烷基、羟基-C₁₋₄ 烷氧基、含氮杂环基、硝基、三氟甲氧基、-COOR⁵（其中 R⁵ 是酯基）、-COR⁶、-CONR⁶R⁷ 或-NR⁶R⁷（其中 R⁶ 和 R⁷ 各为氢或 C₁₋₄ 烷基）； R² 是苯基、萘基或选自噻吩基、吡啶基、苯并噻吩基、喹啉基、苯并呋喃基或苯并腙唑基的杂芳基，所述苯基、萘基和杂芳基被任选取代，或 R² 是被 C₁₋₄ 烷基任选取代的呋喃基； R³ 是腈、羧基、-COOR⁸（其中 R⁸ 是酯基）、-CONR⁹R¹⁰（其中 R⁹ 和 R¹⁰ 分别是氢或 C₁₋₄ 烷基）或-SO₂₋₄烷基、或-SO₂R¹¹，其中 R¹¹ 是 C₁₋₄烷基、任选取代的苯基或任选取代的苯基-C₁₋₄烷基；和 R⁴ 是 1-吡咯基、1-咪唑基或 1-吡唑基，所述 1-吡咯基、1-咪唑基和 1-吡唑基可任选被一个或两个 C₁₋₄烷基、羧基、羟基-C₁₋₄烷基或 -CHO 基团取代，或 1-(1,2、1-(1,2,3,4-三唑基)、1-(1,3,4-三唑基)或 2-(1,2,3-三唑基)，所述三唑基可选择被 C₁₋₄烷基或 C₁₋₄全氟烷基取代，或可选择被 C₁₋₄烷基取代的 1-四唑基； 及其盐类。
• Synthesis and antifungal activity of some 3-benzylidenechroman-4-ones, 3-benzylidenethiochroman-4-ones and 2-benzylidene-1-tetralones
  作者：T Al Nakib、V Bezjak、MJ Meegan、R Chandy

  DOI：10.1016/0223-5234(90)90010-z

  日期：1990.6
• 2-Substituted indazoles. Synthesis and antimicrobial activity
  作者：Tamás Lóránd、Béla Kocsis、Levente Emôdy、Pál Sohár

  DOI：10.1016/s0223-5234(99)00120-8

  日期：1999.11

  2-Isothiocarbamoyl substituted fused pyrazolines and their S-alkvl derivatives were prepared as potentially antimicrobial agents. Conventional methods were used to synthesize the novel derivatives starting from cyclic unsaturated ketones and thiosemicarbazide under acidic catalyst. These cyclizations yielded only one diastereoisomer of 3-H, 3a-H cis. The alkylations were performed applying alkyl halides. The structures of the new compounds, including configurations and conformations, were elucidated by NMR spectroscopy, also making use of 2D-HSC, DEFT and DNOE measurements. The S-alkyl derivatives were evaluated for activity against Gram-negative and Gram-positive bacteria and their in vitro toxicity was determined on HeLa cells. The structure-activity relationship was also studied. (C) 1999 Editions scientifiques et medicales Elsevier SAS.