(E)-6'-(3,4-dichlorobenzylidene)-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3] dithiolane-2,2'-naphthalen]-5'(6'H)-one | 1289642-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-6'-(3,4-dichlorobenzylidene)-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3] dithiolane-2,2'-naphthalen]-5'(6'H)-one
• 英文别名: (2'E)-2'-[(3,4-dichlorophenyl)methylidene]-8'a-methylspiro[1,3-dithiolane-2,6'-3,4,7,8-tetrahydronaphthalene]-1'-one
• CAS: 1289642-60-9
• 化学式: C₂₀H₂₀Cl₂OS₂
• 分子量: 411.416
• InChiKey: KWARJRDWYZWFSX-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,4,7,8,8a-hexahydro-8a-methyl-6-ethylenedithioketal-1-naphthalene 、 3,4-二氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.17h， 以51%的产率得到(E)-6'-(3,4-dichlorobenzylidene)-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3] dithiolane-2,2'-naphthalen]-5'(6'H)-one
  参考文献：
  名称：

  Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors

  摘要：

  Chalcone type compound 1a ((E)-6'-benzylidene-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one) was discovered as an potent inhibitor in melanogenesis. To define its structure-activity relationship, a series of analogs 1b-n, dithiolane truncated 2a-b and ring A removed 3a-e were prepared and evaluated. The electron donating substitution on the phenyl ring (ring C) rather than an electron withdrawing group and dithiolane motif of 1 are needed for the activity enhancement. The scaffold containing both rings A and B associated with alpha,beta-unsaturated system connected to phenyl of 1 was essential for antimelanogenesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.060