2,6-Bis-[1-naphthalen-1-yl-meth-(E)-ylidene]-cyclohexanone | 62085-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-Bis-[1-naphthalen-1-yl-meth-(E)-ylidene]-cyclohexanone
• 英文别名: 2,6-Bis(1-naphthylmethylene)cyclohexanone；(2E,6E)-2,6-bis(naphthalen-1-ylmethylidene)cyclohexan-1-one
• CAS: 62085-76-1
• 化学式: C₂₈H₂₂O
• 分子量: 374.482
• InChiKey: RQLOEGRFORZSTA-SIHVKLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,6-Bis-[1-naphthalen-1-yl-meth-(E)-ylidene]-cyclohexanone 、 [(苯基甲亚基)氨基]乙酸甲酯 在 (S)-N-((S)-(4-(tert-butyl)phenyl)((1R,4S)-4,5-dimethyl-3,6-diphenyl-1-phosphabicyclo[2.2.1]hepta-2,5-dien-2-yl)methyl)-2-methylpropane-2-sulfinamide 、 potassium carbonate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以81%的产率得到methyl (1R,3R,4R,5S,E)-4-(naphthalen-1-yl)-7-(naphthalen-1-ylmethylene)-6-oxo-1-phenyl-2-azaspiro[4.5]decane-3-carboxylate
  参考文献：
  名称：

  Ag / P-Stereogenic膦催化的对映选择性1,3-偶极环加成反应：一种光学活性吡咯烷酮的方法

  摘要：

  报道了Ag / P-立体异构的膦复合物催化的偶氮甲亚胺的1,3-偶极环加成与缺电子的烯烃。在该反应中，获得了具有螺四元立体构型中心的高度官能化的吡咯啉，收率好（高达99％），非对映体（高达> 20：1 dr）和对映体选择性（高达> 99％ee） 。加合物的手性主要受P-立体生成的膦所控制。

  DOI：

  10.1021/acs.orglett.9b00926
• 作为产物：
  描述：

  1-环己烯氧基三甲基硅烷 、 [乙酰氧基(萘-1-基)甲基]乙酸酯 在 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以88%的产率得到2,6-Bis-[1-naphthalen-1-yl-meth-(E)-ylidene]-cyclohexanone
  参考文献：
  名称：

  酰基缩醛化学，第 IV 部分：BF3 催化由缩醛缩醛和 1-环烯基三甲基甲硅烷基醚生成取代的 α,α'-双（芳基亚甲基）环烷酮

  摘要：

  当在室温下用三氟化硼处理芳族醛酰基和 1-环烯基三甲基甲硅烷基醚在二氯甲烷中的混合物时，会形成相应的 α,α'-双(芳基亚甲基)环烷酮。产率对缩醛/醚的比例和酰基的结构都很敏感。当含有二乙酰氧基部分的酰基与 1-环己烯基三甲基甲硅烷基醚以 2:1 的缩醛与醚的比例反应时，获得了最高 97% 的产率。

  DOI：

  10.1055/s-2007-990881

文献信息

• Antimycobacterial activity of novel 1,2,4-oxadiazole-pyranopyridine/chromene hybrids generated by chemoselective 1,3-dipolar cycloadditions of nitrile oxides
  作者：Raju Ranjith Kumar、Subbu Perumal、J. Carlos Menéndez、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2011.04.033

  日期：2011.6

  The 1,3-dipolar cycloaddition of nitrile oxides generated in situ from benzohydroximinoyl chloride and triethylamine to 2-aminopyranopyridine-3-carbonitriles and 2-aminochromene-3-carbonitriles occurred chemoselectively furnishing novel 1,2,4-oxadiazole-pyranopyridine/chromene hybrid heterocycles in moderate yields. In vitro screening of these compounds against Mycobacterium tuberculosis H37Rv (MTB)

  由苯并氢氧亚甲基氯和三乙胺就地生成的腈的1，3-偶极环加成反应生成2-氨基吡咯并吡啶-3-甲腈和2-氨基氧化烯-3-甲腈的化学选择性提供了新的1,2,4-恶二唑-吡喃吡啶/色烯杂化物中等产量的杂环。这些化合物针对结核分枝杆菌H37Rv（MTB）的体外筛选显示，1,2,4-恶二唑-吡喃并吡啶杂化物相对于1,2,4-恶二唑-色烯杂化物表现出增强的活性。在筛选的化合物中，3- [3-（4-氯苯基）-1,2,4-恶二唑-5-基] -4-（2,4-二氯苯基）-8-[（E）-（2,4 -（二氯苯基）-亚甲基] -6-甲基-5,6,7,8-四氢-4 H-吡喃并[3,2- c] pyridin-2-amine（MIC：0.31μM）的活性是标准抗结核药的1.2倍，15.2倍和24.6倍。分别为异烟肼，环丙沙星和乙胺丁醇。
• An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones
  作者：Raju Ranjith Kumar、Subbu Perumal、S.C. Manju、Pritesh Bhatt、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2009.05.018

  日期：2009.7

  s afforded novel spiro-heterocycles chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Two compounds, 4-(2,4-dichlorophenyl)-5-phenylpyrrolo(spiro[2.2″]acenaphthene-1″-one)spiro[3.2′]-6′-(2,4-dichlorophenylmethylidene)cyclohexanone (4i) and spiro[5.2″]acena

  衍生自啶醌和α-氨基酸的偶氮甲亚胺的1，3-偶极环加成。肌氨酸，苯基甘氨酸，1,3-噻唑烷-4-羧酸和脯氨酸生成一系列2,6-双[（E）-芳基亚甲基]环己酮，可定量定量提供新型螺-杂环化学，区域和立体选择性。使用琼脂稀释法筛选这些化合物对结核分枝杆菌H37Rv（MTB）的体外活性。两种化合物4-（2,4-二氯苯基）-5-苯基吡咯并（螺[2.2“]]-1-1-）螺[3.2']-6'-（2,4-二氯苯基亚甲基）环己酮（4i）和螺[5.2“] ena-1” -onespiro [6.2']-6'-（2,4-二氯苯基亚甲基）环己酮-7-（2,4-二氯苯基）四氢-1 H-吡咯并[1,2- c ] [1,3]噻唑（5i）在体外表现出最大活性，对MTB的MIC值为0.40μg/ mL，分别比乙胺丁醇和吡嗪酰胺强4到15.6倍。
• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：Bowen J. Phillip

  公开号：US20090018167A1

  公开（公告）日：2009-01-15

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiogenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及用作血管生成抑制剂的查尔酮和查尔酮衍生物和类似物。这些廉价合成的化合物表现出意外的良好的血管生成抑制活性。本发明还涉及将查尔酮及其类似物用作抗肿瘤/抗癌剂，并用于治疗许多与血管生成有关的疾病或病态，包括血管生成性皮肤疾病，如银屑病、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等，以及慢性炎症性疾病，如关节炎。
• Anomalous behaviour of Rh(II)-generated carbonyl ylides: entry into functionalized spiro dioxa-bridged polycyclic frameworks
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan

  DOI：10.1016/s0040-4039(02)00626-3

  日期：2002.5

  A series of symmetrical alpha,beta-unsaturated ketone systems having multiple pi-bonds were synthesized. To generate five-membered-ring carbonyl ylides as intermediates. the rhodium(II)-catalyzed reactions of alpha-diazo ketones were carried out and the carbonyl ylides reacted with the pi-bonded alpha,beta-unsaturated ketone systems. Functionalized spiro dioxa-bridged polycyclic ring systems were produced with high regio- and chemoselectivity in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Sequential 1,3-Dipolar Cycloadditions in the Synthesis of Novel Tri-spiro Cyclohexanones and Piperidin-4-ones
  作者：Raju Ranjith Kumar、Balaganesan Loganayaki、Subbu Perumal

  DOI：10.1080/00397910902735373

  日期：2009.8.20

  The sequential 1,3-dipolar cycloadditions of azomethine ylide and nitrile oxide to a series of 2,6-bis[(E)-arylmethylidene]cyclohexanones and 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel tri-spiro heterocycles comprising isoxazoline, pyrrolidine and acenaphthylen-1(2H)-one rings in good yields and stereoselectivity.