1,1-dichloro-1a,9b-dihydrocyclopropaphenanthrene | 37608-29-0

• 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: 1,1-dichloro-1a,9b-dihydrocyclopropaphenanthrene
• 英文别名: 1,1-dichloro-1a,9b-dihydrocyclopropa[l]phenanthrene；7,7-Dichlordibenzonorcaran；7,7-Dichlor-dibenzobicyclo(4,1,0)-heptan；(1aS,9bR)-1,1-dichloro-1a,9b-dihydrocyclopropa[l]phenanthrene
• CAS: 37608-29-0
• 化学式: C₁₅H₁₀Cl₂
• 分子量: 261.15
• InChiKey: HQGMQJUEHLYMOY-OKILXGFUSA-N

物化性质

• 熔点：
  142 °C(Solv: acetone (67-64-1))
• 沸点：
  399.8±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 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：

  1,1-dichloro-1a,9b-dihydrocyclopropaphenanthrene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5H-二苯并[a,c]环庚烯-5-酮
  参考文献：
  名称：

  Blume,G. et al., Justus Liebigs Annalen der Chemie, 1975, p. 201 - 208

  摘要：

  DOI：
• 作为产物：
  描述：

  氯仿 、 菲 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 生成 1,1-dichloro-1a,9b-dihydrocyclopropaphenanthrene
  参考文献：
  名称：

  Blume,G. et al., Justus Liebigs Annalen der Chemie, 1975, p. 201 - 208

  摘要：

  DOI：

文献信息

• Photochemical Generation of Strained Cycloalkynes from Methylenecyclopropanes
  作者：Daniel P. Maurer、Rui Fan、Dasan M. Thamattoor

  DOI：10.1002/anie.201701275

  日期：2017.4.10

  anthrene and 1‐cyclobutylidene‐1a,9b‐dihydro‐1H‐cyclopropa[l]phenanthrene undergo photolysis in solution at ambient temperature to produce cyclohexyne and cyclopentyne, respectively. These strained cycloalkynes, formed via the putative cycloalkylidenecarbenes, were intercepted as Diels–Alder adducts. Calculations at the CCSD(T)/cc‐pVTZ//B3LYP/6‐31+G* level of theory show that singlet cyclopentylidenecarbene

  烃1–环亚戊基-1a，9b-二氢-1H-环丙烷[ l ]菲和1–环丁烯-1a，9b-二氢-1H-环丙烷[ l ]菲在环境温度下在溶液中发生光分解以生成环己炔和环戊炔。这些通过假定的亚环烷基碳烯形成的应变炔烃被截获为狄尔斯-阿尔德加合物。在CCSD（T）/ cc-pVTZ // B3LYP / 6-31 + G *理论水平上的计算表明，单重态环戊叉碳烯必须克服9.1 kcal mol -1的障碍才能重排成环己炔（使用ΔE进行环扩环） = -15.1大卡摩尔-1）。相比之下，环丁烯卡宾仅需克服1.6 kcal mol -1的势垒即可重排成环戊炔（环扩展的ΔE = -6.2 kcal mol -1）。
• Luckenbach,R.; Mueller,N., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1979, vol. 34, p. 464 - 480
  作者：Luckenbach,R.、Mueller,N.

  DOI：——

  日期：——
• 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).
• Blume,G. et al., Justus Liebigs Annalen der Chemie, 1975, p. 201 - 208
  作者：Blume,G. et al.

  DOI：——

  日期：——