2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-6-methyl-cyclohexanone | 58000-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-6-methyl-cyclohexanone
• 英文别名: 2-(4-Methoxybenzylidene)-6-methylcyclohexanone；(2E)-2-[(4-methoxyphenyl)methylidene]-6-methylcyclohexan-1-one
• CAS: 58000-07-0
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: QGMNVHNWJKXOLJ-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 2-甲基环己酮 在 bis(cyclopentadienyl)diphenyltitanium(IV) 作用下， 反应 23.0h， 以57%的产率得到2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-6-methyl-cyclohexanone
  参考文献：
  名称：

  A Convenient Synthesis of α,α′-Bis(substitutedbenzylidene)cycloalkanones

  摘要：

  Cp2TiPh2催化的环戊酮或环己酮与苯甲醛的反应，实现了交叉 aldol 缩合，在比之前报告的条件更温和的条件下，以良好的产率生成相应的 2,5-双(取代苄基)环戊酮或 2,6-双(取代苄基)环己酮。

  DOI：

  10.1246/cl.1993.2157

文献信息

• A Convenient Synthesis of α,α′-Bis(substitutedbenzylidene)cycloalkanones
  作者：Taich Nakano、Toshihiko Migita

  DOI：10.1246/cl.1993.2157

  日期：1993.12

  The Cp2TiPh2-catalyzed reaction of cyclopentanone or cyclohexanones with benzaldehydes brought about the cross-aldol condensation to give the corresponding 2,5-bis(substitutedbenzylidene)cyclopentanones or 2,6-bis(substitutedbenzylidene)cyclohexanones in good yields under milder conditions than those previouly reported.

  Cp2TiPh2催化的环戊酮或环己酮与苯甲醛的反应，实现了交叉 aldol 缩合，在比之前报告的条件更温和的条件下，以良好的产率生成相应的 2,5-双(取代苄基)环戊酮或 2,6-双(取代苄基)环己酮。
• 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.