8-(trideuteriomethyl)naphthalene-1-carboxylic acid | 135733-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(trideuteriomethyl)naphthalene-1-carboxylic acid
• CAS: 135733-99-2
• 化学式: C₁₂H₁₀O₂
• 分子量: 189.186
• InChiKey: FLBHUCKQJRXXQB-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  8-(trideuteriomethyl)naphthalene-1-carboxylic acid 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 反应 26.0h， 生成 8-(trideuteriomethyl)-1-naphthaldehyde (p-tolylsulfonyl)hydrazone
  参考文献：
  名称：

  A carbene to biradical rearrangement: reaction paths from (8-methyl-1-naphthyl)carbene to acenaphthene

  摘要：

  Photochemical nitrogen elimination from 1-(diazomethyl)-8-methylnaphthalene (2) yields acenaphthene (3) via the reactive intermediates (8-methyl-1-naphthyl)carbene (a) and 1,8-naphthoquinodimethane (b). The triplet biradical b was observed by absorption spectroscopy at 77 K and by laser flash photolysis at room temperature. The cyclization of triplet b to triplet 3 is forbidden by state symmetry. Two pathways for the reaction b --> 3 have been identified: (1) intersystem crossing to the singlet groud state is rate-determining in the thermal decay of b, and (2) an adiabatic reaction yielding 3 in the lowest excited triplet state was observed upon photolysis of triplet b at 77 K. The carbene precursor of b was intercepted by methanol. This resulted in a reduced yield of transient b in acetonitrile. The trapping reaction did not obey a linear Stern-Volmer relationship.

  DOI：

  10.1021/ja00021a037
• 作为产物：
  描述：

  1H,3H-benzo[de]isochromen-1-one-3,3-d2 在 palladium on activated charcoal 氘氧化钠 、 氘 作用下， 以 重水 为溶剂， 反应 288.0h， 以6.7 g的产率得到8-(trideuteriomethyl)naphthalene-1-carboxylic acid
  参考文献：
  名称：

  A carbene to biradical rearrangement: reaction paths from (8-methyl-1-naphthyl)carbene to acenaphthene

  摘要：

  Photochemical nitrogen elimination from 1-(diazomethyl)-8-methylnaphthalene (2) yields acenaphthene (3) via the reactive intermediates (8-methyl-1-naphthyl)carbene (a) and 1,8-naphthoquinodimethane (b). The triplet biradical b was observed by absorption spectroscopy at 77 K and by laser flash photolysis at room temperature. The cyclization of triplet b to triplet 3 is forbidden by state symmetry. Two pathways for the reaction b --> 3 have been identified: (1) intersystem crossing to the singlet groud state is rate-determining in the thermal decay of b, and (2) an adiabatic reaction yielding 3 in the lowest excited triplet state was observed upon photolysis of triplet b at 77 K. The carbene precursor of b was intercepted by methanol. This resulted in a reduced yield of transient b in acetonitrile. The trapping reaction did not obey a linear Stern-Volmer relationship.

  DOI：

  10.1021/ja00021a037