3,4-dihydro-5,8-dimethoxy-2-methyl-1(2H)-naphthalenone | 6394-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-5,8-dimethoxy-2-methyl-1(2H)-naphthalenone
• 英文别名: 5,8-Dimethoxy-2-methyl-1-keto-1,2,3,4-tetrahydro-naphthalin；5,8-dimethoxy-2-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 6394-85-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QNCLXOORAAEFIX-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  368.8±42.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3,4-dihydro-5,8-dimethoxy-2-methyl-1(2H)-naphthalenone 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 2-(hydroxymethyl)-5,8-dimethoxy-2-methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to a carbonyl group

  摘要：

  Racemic compounds containing a quaternary stereocenter (having hydroxymethyl and alkyl group adjacent to keto functionality) based on chromanone, alpha-tetralone, and indalone scaffolds have been synthesized. An enzymatic irreversible transesterification approach has been applied to generate the pure enantiomers in a stereocontrolled fashion. The pure enantiomers of some alpha,alpha-dialkylated carbonyl compounds have been synthesized by this method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.024
• 作为产物：
  描述：

  3,6-dimethoxy-1-(1-methylethenyl)benzocyclobuten-1-ol 以 甲苯 为溶剂， 反应 48.0h， 以65%的产率得到3,4-dihydro-5,8-dimethoxy-2-methyl-1(2H)-naphthalenone
  参考文献：
  名称：

  苯并环丁烯酮经顺序热电循环反应制备取代的3,4-二氢-1（2 H）-萘酮

  摘要：

  由苯并环丁烯酮通过添加烯基格利雅试剂或添加炔基锂试剂，然后经（E）选择性还原而制得的1-烯基苯并环丁烯醇，经过连续的4π和6π热电环化反应生成取代的3,4-二氢-1（2 H） -萘酮。类似的序列从萘并[b]环丁烯-1（2 H）-1得到3,4，-二氢-1（2 H）-蒽酮。

  DOI：

  10.1016/0040-4020(95)01054-8

文献信息

• The preparation of α-tetralones from benzocyclobutenones via sequential thermal electrocyclic reactions
  作者：Derek N. Hickman、Timothy W. Wallace、J. Michael Wardleworth

  DOI：10.1016/s0040-4039(00)74896-9

  日期：1991.2

  1-Alkenylbenzocyclobuten-1-ols, prepared from benzocyclobutenones via the addition of alkenylmagnesium bromides, or the addition of alkynyllithium reagents followed by (E)-selective reduction of the triple bond, undergo successive thermal 4-pi and 6-pi electrocyclic reactions leading to substituted 3,4-dihydro-1(2H)-naphthalenones.
• GILES, ROBIN G. F.;GREEN, IVAN R., S. AFR. J. CHEM., 43,(1990) N-4, C. 91-95
  作者：GILES, ROBIN G. F.、GREEN, IVAN R.

  DOI：——

  日期：——
• MASUI, MORIYASU;ANDO, AKIRA;SHIOIRI, TAKAYUKI, TETRAHEDRON LETT., 29,(1988) N 23, C. 2835-2838
  作者：MASUI, MORIYASU、ANDO, AKIRA、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——
• The preparation of substituted 3,4-dihydro-l(2H)-naphthalenones from benzocyclobutenones via sequential thermal electrocyclic reactions
  作者：Derek N. Hickman、Kevin J. Hodgetts、Peter S. Mackman、Timothy W. Wallace、J.Michael Wardleworth

  DOI：10.1016/0040-4020(95)01054-8

  日期：1996.2

  alkynyllithium reagents followed by (E)-selective reduction, undergo successive thermal 4π and 6π electrocyclisations to give substituted 3,4-dihydro-1(2H)-naphthalenones. An analogous sequence gave 3,4,-dihydro-1(2H)-anthracenone from naphtho[b]cyclobuten-1(2H)-one.

  由苯并环丁烯酮通过添加烯基格利雅试剂或添加炔基锂试剂，然后经（E）选择性还原而制得的1-烯基苯并环丁烯醇，经过连续的4π和6π热电环化反应生成取代的3,4-二氢-1（2 H） -萘酮。类似的序列从萘并[b]环丁烯-1（2 H）-1得到3,4，-二氢-1（2 H）-蒽酮。
• Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to a carbonyl group
  作者：Tridib Mahapatra、Nandan Jana、S. Nanda

  DOI：10.1016/j.tetasy.2008.04.024

  日期：2008.5

  Racemic compounds containing a quaternary stereocenter (having hydroxymethyl and alkyl group adjacent to keto functionality) based on chromanone, alpha-tetralone, and indalone scaffolds have been synthesized. An enzymatic irreversible transesterification approach has been applied to generate the pure enantiomers in a stereocontrolled fashion. The pure enantiomers of some alpha,alpha-dialkylated carbonyl compounds have been synthesized by this method. (C) 2008 Elsevier Ltd. All rights reserved.