3-methylidene-2-phenylchroman-4-one | 77038-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-methylidene-2-phenylchroman-4-one
• 英文别名: 3-methylene flavanone；3-Methyleneflavanone；3-methylidene-2-phenylchromen-4-one
• CAS: 77038-06-3
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: MOLVQHHXMFNNFM-UHFFFAOYSA-N

物化性质

• 沸点：
  397.7±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylidene-2-phenylchroman-4-one 、 methyl (E)-N-(2-naphthylmethylidene)alaninate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver(l) oxide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以48%的产率得到methyl (2'S,3S,5'S)-2'-methyl-5'-naphthalen-2-yl-4-oxo-2-phenylspiro[2H-chromene-3,4'-pyrrolidine]-2'-carboxylate
  参考文献：
  名称：

  Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels–Alder reactions

  摘要：

  The locked s-cis enone system present in 3-methylenequinol-4-ones and chroman-4-ones offers substantial further synthetic opportunities as illustrated by the ability to function as a 2 pi-component in 1,3-dipolar cycloaddition reactions, or as a 2 pi- or 4 pi-component in Diels-Alder reactions. Cascade molecular queuing-cycloadditions/cyclocondensation are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01177-1
• 作为产物：
  描述：

  3-<(dimethylamino)methyl>flavanone hydrochloride 以 水 为溶剂， 反应 2.0h， 以12%的产率得到3-methylidene-2-phenylchroman-4-one
  参考文献：
  名称：

  Antimicrobial 3-methylene flavanones

  摘要：

  The antimicrobial activity previously attributed to flavanone Mannich bases was found to be due to their breakdown products, 3-methyleneflavanones. Among the latter compounds, highest potency was observed when the flavanone phenyl ring contained bromine or chlorine substituents. 3-Methylene-2-phenylflavanone (8) was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.

  DOI：

  10.1021/jm00141a011

文献信息

• Synthesis and Cytotoxic Evaluation of 3-Methylidenechroman-4-ones
  作者：Jacek Kędzia、Tomasz Bartosik、Joanna Drogosz、Anna Janecka、Urszula Krajewska、Tomasz Janecki

  DOI：10.3390/molecules24101868

  日期：——

  Horner–Wadsworth–Emmons reagents giving 2-substituted 3-methylidenechroman-4-ones, which were then tested for their possible cytotoxic activity against two leukemia cell lines, HL-60 and NALM-6, and against MCF-7 breast cancer cell line. All new compounds (14a–o) were highly cytotoxic for the leukemic cells and showed a moderate or weak effect on MCF-7 cells. Analog 14d exhibited the highest growth inhibitory

  在寻找新的抗癌剂的过程中，使用 Horner-Wadsworth-Emmons 方法合成了一个不同取代的 3-methylidenechroman-4-ones 库。甲基膦酸二乙酯与选定的水杨酸乙酯的酰化提供了 3-二乙氧基磷酰基色烯-4-酮，接下来将其用作与各种格氏试剂反应的迈克尔受体。加合物以反式和顺式非对映异构体以及少量烯醇形式的混合物形式获得。通过NMR分析确定了它们的相对构型和优选构象。结果证明，这些加合物是有效的 Horner-Wadsworth-Emmons 试剂，可产生 2-取代的 3-methylidenechroman-4-ones，然后测试它们对两种白血病细胞系 HL-60 和 NALM-6 的可能的细胞毒活性，以及​​对MCF-7 乳腺癌细胞系。所有新化合物 (14a-o) 对白血病细胞具有高度细胞毒性，对 MCF-7 细胞显示出中等或微弱的作用。类似物 14d 对
• 3-Methylene flavanones and 3-methylene chromanones
  申请人：Miles Laboratories, Inc.

  公开号：US04241069A1

  公开（公告）日：1980-12-23

  Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: ##STR1## wherein: R.sup.1 is a member selected from the group consisting of hydrogen, Br, CH.sub.3 and OCH.sub.3 ; R.sup.2 is selected from the group consisting of hydrogen and ##STR2## wherein R.sup.4 is a member selected from the group consisting of hydrogen, Br, Cl, CH.sub.3, OCH.sub.3, NO.sub.2, N(CH.sub.3).sub.3 and CN; R.sup.5 is selected from the group consisting of hydrogen and Cl, with the proviso that when R.sup.5 is Cl, R.sup.4 is hydrogen or Cl; and R.sup.3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R.sup.3 is naphthyl, R.sup.1 and R.sup.2 are hydrogen.

  揭示了对微生物具有活性的3-亚甲基黄酮和3-亚甲基色酮类化合物。这些化合物由以下一般结构式表示：其中：R.sup.1是从氢、Br、CH.sub.3和OCH.sub.3组成的群体中选取的成员；R.sup.2是从氢和##STR2##组成的群体中选取的成员，其中R.sup.4是从氢、Br、Cl、CH.sub.3、OCH.sub.3、NO.sub.2、N(CH.sub.3).sub.3和CN组成的群体中选取的成员；R.sup.5是从氢和Cl组成的群体中选取的成员，但有一个条件是当R.sup.5是Cl时，R.sup.4是氢或Cl；R.sup.3是从氢、苯基、2-噻吩基、4-吡啶基和萘基组成的群体中选取的成员，但有一个条件是当R.sup.3是萘基时，R.sup.1和R.sup.2是氢。
• 3-Methylene flavanones and 3-methylene chromanones, antimicrobial composition containing same and method of inhibiting the growth of microorganisms
  申请人：MILES LABORATORIES, INC.

  公开号：EP0025161A1

  公开（公告）日：1981-03-18

  Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: wherein: R' is a member selected from the group consisting of hydrogen, Br, CH3 and OCH3; R2 is selected from the group consisting of hydrogen and wherein R4 is a member selected from the group consisting of hydrogen, Br, Cl, CH3, OCH3, NO2, N/CH3)2, C(CH3)3 and CN; R' is selected from the group consisting of hydrogen and Cl, with the proviso that when R5 is Cl, R' is hydrogen or Cl; and R3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R3 is naphthyl, R1 and R2 are hydrogen.

  本发明公开了具有抗微生物活性的 3-亚甲基黄烷酮和 3-亚甲基色满酮化合物。这些化合物由一般结构式表示： 其中R'选自由氢、Br、CH3 和 O 组成的组 其中 R4 选自由氢、Br、Cl、 、O 、NO2、N/ )2、C( )3 和 CN 组成的组；R'选自由氢和 Cl 组成的组，但当 R5 为 Cl 时，R'为氢或 Cl；以及 R3 选自由氢、苯基、2-噻吩基、4-吡啶基和萘基组成的组，但当 R3 为萘基时，R1 和 R2 为氢。
• Pharmaceutical preparations containing flavanone or thioflavanone derivatives, the use thereof, novel flavanones and thioflavanones, and processes for their manufacture
  申请人：Zyma SA

  公开号：EP0139614A2

  公开（公告）日：1985-05-02

  The invention relates to pharmaceutical preparations containing compounds of formula I in which X represents unsubstituted or substituted amino or a quaternary ammonium salt; halogen, free, etherified or esterified hydroxy; free, etherified, esterified or oxidized mercapto; free or functionally modified carboxyl, free or functionally modified sulfo; acyl; nitro; an unsubstituted or substituted hydrocarbon radical or an unsubstituted or substituted heterocyclic radical, Y represents oxygen, sulfur, sulfinyl or sulfonyl but must be oxygen, sulfinyl or sulfonyl, if X is 1H-imidazol-1-yl, and rings A and B are each unsubstituted or substituted; or pharmaceutically acceptable salts of such compounds that contain a salt-forming group, and to novel compounds of formula I. The compounds are useful e.g. for the treatment of diseases of the respiratory tract and of liver diseases. They are prepared by methods known per se.

  本发明涉及含有式 I 化合物的药物制剂。 其中 X 代表未取代或取代的氨基或季铵盐；卤素；游离的、醚化的或酯化的羟基；游离的、醚化的、酯化的或氧化的巯基；游离的或功能修饰的羧基；游离的或功能修饰的磺基；酰基；硝基；未取代或取代的烃基或未取代或取代的杂环基，Y 代表氧、硫、亚砜基或磺酰基，但如果 X 是 1H-imidazol-1-yl 则必须是氧、亚砜基或磺酰基，且环 A 和 B 各自是未取代或取代的；或含有成盐基团的此类化合物的药学上可接受的盐，以及式 I 的新型化合物。这些化合物可用于治疗呼吸道疾病和肝脏疾病等。它们的制备方法本身是已知的。
• Amine-Catalyzed Coupling of Allenic Esters to α,β-Unsaturated Carbonyls
  作者：Catherine A. Evans、Scott J. Miller

  DOI：10.1021/ja0377798

  日期：2003.10.1

  Nucleophilic amines catalyze the 1,4-addition of allenic esters to alpha,beta-unsaturated carbonyl compounds. The reactions proceed under mild conditions. In addition, Baylis-Hillman products serve as appropriate electrophiles for the process such that a one-pot, three-component coupling of aldehydes, acrylates, and allenic esters may be achieved.