1,4-dimethoxy-2-pivaloylnaphthalene | 177028-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dimethoxy-2-pivaloylnaphthalene
• 英文别名: 1-(1,4-Dimethoxy-2-naphthalenyl)-2,2-dimethyl-1-propanone；1-(1,4-dimethoxynaphthalen-2-yl)-2,2-dimethylpropan-1-one
• CAS: 177028-17-0
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: OYWTYCCJSXDYTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  1,4-dimethoxy-2-pivaloylnaphthalene 在 lithium aluminium tetrahydride 、 titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到3-(1-hydroxy-2,2-dimethylpropyl)-1-methoxynaphthalene
  参考文献：
  名称：

  Thermochromic Furofurans. IV. Approach to the synthesis of bridgehead substituted furo[3,2-b]furans and side products of McMurry reactions

  摘要：

  Substituted dihydroxystilbenes 2 are suitable starting materials for the synthesis of photochromic systems derived from 3/4. Attempts to couple the naphthones 8a-8e by the McMurry reaction with TiCl3/LiAlH4 yielded mainly reduction products such as 8f, g or 9. However, the furofuran 3b was isolated when using the zinc-copper couple for reduction. The helicene 11 was formed as an unexpected byproduct in the McMurry reaction of the pivaloylnaphthalene 8d.

  DOI：

  10.1002/prac.19963380127
• 作为产物：
  描述：

  1,4-二甲氧基萘 、 三甲基乙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以58.6%的产率得到1,4-dimethoxy-2-pivaloylnaphthalene
  参考文献：
  名称：

  Thermochromic Furofurans. IV. Approach to the synthesis of bridgehead substituted furo[3,2-b]furans and side products of McMurry reactions

  摘要：

  Substituted dihydroxystilbenes 2 are suitable starting materials for the synthesis of photochromic systems derived from 3/4. Attempts to couple the naphthones 8a-8e by the McMurry reaction with TiCl3/LiAlH4 yielded mainly reduction products such as 8f, g or 9. However, the furofuran 3b was isolated when using the zinc-copper couple for reduction. The helicene 11 was formed as an unexpected byproduct in the McMurry reaction of the pivaloylnaphthalene 8d.

  DOI：

  10.1002/prac.19963380127

文献信息

• Thermochromic Furofurans. IV. Approach to the synthesis of bridgehead substituted furo[3,2-b]furans and side products of McMurry reactions
  作者：Hartmut Laatsch、Antti Talvitie、Andreas Kral、Bernd-Peter Ernst、Mathias Noltemeyer

  DOI：10.1002/prac.19963380127

  日期：——

  Substituted dihydroxystilbenes 2 are suitable starting materials for the synthesis of photochromic systems derived from 3/4. Attempts to couple the naphthones 8a-8e by the McMurry reaction with TiCl3/LiAlH4 yielded mainly reduction products such as 8f, g or 9. However, the furofuran 3b was isolated when using the zinc-copper couple for reduction. The helicene 11 was formed as an unexpected byproduct in the McMurry reaction of the pivaloylnaphthalene 8d.