2'-hydroxy-4',5'-methylenedioxychalcone | 96249-79-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-hydroxy-4',5'-methylenedioxychalcone
• 英文别名: 2'-hydroxy-4',5'-methylenedioxy-trans-chalcone；2'-Hydroxy-4',5'-methylendioxy-trans-chalkon；1-(6-Hydroxy-1,3-benzodioxol-5-yl)-3-phenyl-2-propen-1-one；(E)-1-(6-hydroxy-1,3-benzodioxol-5-yl)-3-phenylprop-2-en-1-one
• CAS: 96249-79-5
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: XJKKLFWCBUZGIJ-VOTSOKGWSA-N

物化性质

• 熔点：
  117-119 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  490.0±45.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4',5'-methylenedioxychalcone 在 selenium(IV) oxide 、 戊醇 作用下， 生成 6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one
  参考文献：
  名称：

  Romeo; Bargellini, Annali di Chimica, 1952, vol. 42, p. 361,368

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethan-1-one 在 氢氧化钾 、 sodium hydroxide 、 苯甲醛 作用下， 生成 2'-hydroxy-4',5'-methylenedioxychalcone
  参考文献：
  名称：

  Romeo; Bargellini, Annali di Chimica, 1952, vol. 42, p. 361,368

  摘要：

  DOI：

文献信息

• Unusual Friedel-Crafts reactions, IX. One-step ortho-acylation of phenols with α,β-unsaturated acyl chlorides. Synthesis of 2'-hydroxychalcones and sorbicillin analogues
  作者：Franca Bigi、Giovanni Casiraghi、Giuseppe Casnati、Stefania Marchesi、Giovanni Sartori、Carlo Vignali

  DOI：10.1016/0040-4020(84)85088-7

  日期：1984.1

  The reaction of bromomagnesium phenolates 1 in toluene with α, β-unsaturated acyl chlorides 2 at room temperature provides a straightforward highly selective synthesis of α,β-unsaturated 2-hydroxyarylketones 3. 2'-Hydroxychalcones, ortho-sorbylphenols including sorbicillin 3g, and ortho-propiolylphenols were usefully synthesized by this way. This reaction provides a further example of the synthetic

  在室温下，溴化溴化镁苯酚盐1与α，β-不饱和酰氯2的反应提供了α，β-不饱和2-羟基芳基酮3的直接高选择性合成。通过这种方式有用地合成了2'-羟基查耳酮，包括山梨素3g的邻山梨醇基酚和邻丙醇基酚。该反应提供了在苯酚衍生物的精制中螯合控制方法的合成多功能性的另一个实例。
• BIGI, F.;CASIRAGHI, G.;CASNATI, G.;MARCHESI, S.;SARTORI, G.;VIGNALI, C., TETRAHEDRON, 1984, 40, N 20, 4081-4084
  作者：BIGI, F.、CASIRAGHI, G.、CASNATI, G.、MARCHESI, S.、SARTORI, G.、VIGNALI, C.

  DOI：——

  日期：——
• [EN] NOVEL CHALCONE DERIVATIVES WITH CYTOTOXIC ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE CHALCONE PRÉSENTANT UNE ACTIVITÉ CYTOTOXIQUE
  申请人：ADAMED SP ZOO

  公开号：WO2011009826A2

  公开（公告）日：2011-01-27

  Chalcone derivatives of the general formula (I), wherein two from among A, B and Z which are adjacent to each other are linked and form a moiety selected from -O-(CH2)n-S(O)m-, -S(O)m-(CH2)n-O- and -O-(CH2)n-O-, and the remaining one from among A, B and Z is H; or two from among A, B and Z, independently from each other, are selected from a group consisting of OH, -O-C1-C6-alkyl and -S(O)m-C1-C6-alkyl, and the remaining one from among A, B and Z is H; R is H, C1-C6-alkyl, carboxy-C1-C6-alkyl, -(CH2)P- NR1R2 or O(CH2)3NH(CO)CF3, where R1 and R2 both independently are C1-C6-alkyl; or R1 and R2 are linked together to form polymethylene group -(CH2)q-, and with N atom, to which they are attached, form a 5- or 6-membered ring, in which one of carbon atoms may be optionally replaced with O, N, or S; Y is -CH=CH-, -O-, -S- or -CH=N-; X1, X2, X3 independently are H, halogen atom, OH, -C1-C6-alkoxy, carboxy-C1-C6-alkoxyl, di(C1-C6- alkyl)amino-C1-C6-alkoxy, -0-PO(OH)2, NO2 or NH2; m = O, 1 or 2; n = 1 or 2; p = 2 to 6; q = 4 or 5; and acid addition salts, salts with bases and C1-C6-alkyl esters thereof. The compounds may be useful as cytotoxic drugs for the treatment of neoplastic diseases. Formula (I).
• Romeo; Bargellini, Annali di Chimica, 1952, vol. 42, p. 361,368
  作者：Romeo、Bargellini

  DOI：——

  日期：——