1H,3H-benzo[de]isochromen-1-one-3,3-d2 | 135733-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1H,3H-benzo[de]isochromen-1-one-3,3-d2
• CAS: 135733-98-1
• 化学式: C₁₂H₈O₂
• 分子量: 186.178
• InChiKey: UKOVZLWSUZKTRL-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1H,3H-benzo[de]isochromen-1-one-3,3-d2 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氘氧化钠 、 氘 作用下， 以 乙醚 、 重水 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 300.0h， 生成 1-(hydroxymethyl)-8-(trideuteriomethyl)naphthalene
  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：

  1,8-萘二甲酸酐 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以49%的产率得到1H,3H-benzo[de]isochromen-1-one-3,3-d2
  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

文献信息

• The singular reduction of 1,8-bis-hydroxymethylnaphthalene to a benzonorcaradiene by LiAlH4
  作者：Janeta V. Popovici-Müller、Thomas A. Spencer

  DOI：10.1016/s0040-4039(97)10247-7

  日期：1997.11

  Reduction of 1,8-naphthalic anhydride (1) with LiAlH4 in THF (or DME, but not Et2O) affords, in addition to diol 2, benzonorcaradiene 3. Extended treatment of 2 or lactone 4 also leads to 3, in 66% and 65% yield, respectively. Reduction of 4 with LiAID(4) established that formation of 3 proceeds via a symmetrical intermediate. No significant norcaradiene formation is observed upon comparable LiAIH(4) treatment of 14, 15, 16 or 17. This novel reduction of a naphthalene derivative to a benzonorcaradiene appears to be unique to 2 or its precursors. (C) 1997 Elsevier Science Ltd.