(E)-4a'-methyl-6'-(4-methylbenzylidene)-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one | 1289642-56-3

• 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)-4a'-methyl-6'-(4-methylbenzylidene)-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one
• 英文别名: (2'E)-8'a-methyl-2'-[(4-methylphenyl)methylidene]spiro[1,3-dithiolane-2,6'-3,4,7,8-tetrahydronaphthalene]-1'-one
• CAS: 1289642-56-3
• 化学式: C₂₁H₂₄OS₂
• 分子量: 356.553
• InChiKey: AFKOCTGKVSLVCH-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4a'-methyl-6'-(4-methylbenzylidene)-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 乙腈 为溶剂， 以93%的产率得到(E)-8a-methyl-2-(4-methylbenzylidene)-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione
  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
• 作为产物：
  描述：

  对甲基苯甲醛 、 2,3,4,7,8,8a-hexahydro-8a-methyl-6-ethylenedithioketal-1-naphthalene 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.17h， 以54%的产率得到(E)-4a'-methyl-6'-(4-methylbenzylidene)-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

文献信息

• Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors
  作者：Pillaiyar Thanigaimalai、Ki-Cheul Lee、Vinay K. Sharma、Eeda Vekateswara Rao、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2011.02.060

  日期：2011.4

  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.