1ξ-chloro-(1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene | 55831-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1ξ-chloro-(1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene
• 英文别名: 1ξ-Chlor-(1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthren；(1aS,9bR)-1-chloro-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene
• CAS: 55831-21-5
• 化学式: C₁₅H₁₁Cl
• 分子量: 226.705
• InChiKey: LHBIUVDNFVVLDR-YIONKMFJSA-N

物化性质

• 沸点：
  376.6±31.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  吡啶 、 1ξ-chloro-(1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene 以 异辛烷 为溶剂， 反应 0.83h， 生成
  参考文献：
  名称：

  Laser Flash Photolysis Study of Alkylhalocarbenes Generated from Non-Nitrogenous Precursors

  摘要：

  Previously we have studied the photochemistry of alkylchlorodiazirines using laser flash photolysis methods and the pyridine ylide technique (White et al. J. Org. Chem. 1992, 17, 2841). The yield of trappable carbene was found to be a sensitive function of the alkylcarbene structure. This was attributed to ring opening of the diazirine to form a biradical which could suffer rearrangement, in addition to fragmentation to a carbene. It was also possible to explain the data in terms of a carbene-pyridine complex which can either rearrange or collapse to an ylide. In this work, alkylchlorocarbenes are generated from phenanthridenes. The results do not rule out the intermediacy of a carbene-pyridine complex; however, if this species is formed, it does not rearrange to chloroalkene in competition with collapse to form an ylide. This study reduces the urgency with which to postulate carbene-olefin complexes (Tomioka et al. J. Am. Chem. Soc. 1984, 106, 454).

  DOI：

  10.1021/jp972464y
• 作为产物：
  描述：

  (1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene-1c-carbonyl chloride 在 盐酸 、 sodium azide 、 乙醚 、 溶剂黄146 、 丙酮 、 sodium nitrite 作用下， 生成 1ξ-chloro-(1ar,9bc)-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene
  参考文献：
  名称：

  636. yl离子。第五部分。环丙烷[1]-菲衍生物的合成和二苯并[ a，c ]托乙鎓阳离子的尝试形成

  摘要：

  DOI：

  10.1039/jr9590003139

文献信息

• Laser Flash Photolysis Study of Alkylhalocarbenes Generated from Non-Nitrogenous Precursors
  作者：Marc Robert、Igor Likhotvorik、Matthew S. Platz、Sarah C. Abbot、Mary M. Kirchhoff, and、Richard Johnson

  DOI：10.1021/jp972464y

  日期：1998.2.1

  Previously we have studied the photochemistry of alkylchlorodiazirines using laser flash photolysis methods and the pyridine ylide technique (White et al. J. Org. Chem. 1992, 17, 2841). The yield of trappable carbene was found to be a sensitive function of the alkylcarbene structure. This was attributed to ring opening of the diazirine to form a biradical which could suffer rearrangement, in addition to fragmentation to a carbene. It was also possible to explain the data in terms of a carbene-pyridine complex which can either rearrange or collapse to an ylide. In this work, alkylchlorocarbenes are generated from phenanthridenes. The results do not rule out the intermediacy of a carbene-pyridine complex; however, if this species is formed, it does not rearrange to chloroalkene in competition with collapse to form an ylide. This study reduces the urgency with which to postulate carbene-olefin complexes (Tomioka et al. J. Am. Chem. Soc. 1984, 106, 454).
• 636. The tropylium ion. Part V. Synthesis of cyclopropa[1]-phenanthrene derivatives and attempted formation of the dibenzo[a,c]tropylium cation
  作者：M. J. S. Dewar、C. R. Ganellin

  DOI：10.1039/jr9590003139

  日期：——