4-chloro-1,2-dihydrophenanthrene-3-carbaldehyde | 58231-33-7

• 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: 4-chloro-1,2-dihydrophenanthrene-3-carbaldehyde
• 英文别名: 4-Chlor-3-formyl-1,2-dihydrophenanthren
• CAS: 58231-33-7
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: XPCGAHWUGUDTPS-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C(Solv: ethanol (64-17-5))
• 沸点：
  413.3±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-chloro-1,2-dihydrophenanthrene-3-carbaldehyde 在 potassium phosphate 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 、 乙腈 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 platinum(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 29.0h， 生成 10-methyldibenzo[c,g]phenanthrene
  参考文献：
  名称：

  Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior Side of the Helix by Metal-catalyzed Cycloisomerization

  摘要：

  [5]Helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesized by metal-catalyzed cycloisomerization. In addition, novel azulene-fused helicenes have been found through cycloisomerization studies. These [5]helicenes shows a high enough configurationally stability to allow resolution by HPLC on a chiral stationary phase.

  DOI：

  10.1021/ol400332j
• 作为产物：
  描述：

  2,3-二氢-4(1H)-菲酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 以95%的产率得到4-chloro-1,2-dihydrophenanthrene-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior Side of the Helix by Metal-catalyzed Cycloisomerization

  摘要：

  [5]Helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesized by metal-catalyzed cycloisomerization. In addition, novel azulene-fused helicenes have been found through cycloisomerization studies. These [5]helicenes shows a high enough configurationally stability to allow resolution by HPLC on a chiral stationary phase.

  DOI：

  10.1021/ol400332j

文献信息

• Divergent strategy for the synthesis of original dihydrobenzo- and dihydronaphtho-acridines
  作者：Kathleen Solmont、Hamza Boufroura、Amel Souibgui、Pauline Fornarelli、Anne Gaucher、Florence Mahuteau-Betzer、Béchir Ben Hassine、Damien Prim

  DOI：10.1039/c5ob00456j

  日期：——

  Convenient preparation of dihydrobenzo- and dihydronaphtho-acridines that display various rigidity/flexibility and lipophilic/hydrophilic balances.

  方便制备显示不同刚度/柔韧性和疏水/亲水平衡的二氢苯并-和二氢萘并-吖啶。
• New series of acridines and phenanthrolines: synthesis and characterization
  作者：Amel Souibgui、Anne Gaucher、Jérôme Marrot、Flavien Bourdreux、Faouzi Aloui、Béchir Ben Hassine、Damien Prim

  DOI：10.1016/j.tet.2014.02.067

  日期：2014.5

  New series of acridines and phenanthrolines have been prepared from β-chlorovinyl aldehydes and various aniline derivatives allowing the installation of valuable substituents, such as ketone, nitro or amino groups at the heterocyclic core. X-ray analyses confirmed the structures of acridines and phenanthrolines as well as the presence of partially hydrogenated rings and their crucial impact on the

  由β-氯乙烯基醛和各种苯胺衍生物制备了一系列新的a啶和菲咯啉，这些衍生物允许在杂环核心上安装有价值的取代基，例如酮，硝基或氨基。X射线分析证实了cr啶和菲咯啉的结构以及部分氢化的环的存在及其对基于cr啶的体系结构整体形状的关键影响。1 H NMR揭示了几种a啶动机的螺旋行为。还描述了体系结构之间的紫外线数据比较以及部分氢化环数量的影响。
• Synthesis of partially hydrogenated oxa[5] and oxa[6]helicenes from β-chlorovinylaldehydes
  作者：Alexandre Requet、Amel Souibgui、Grégory Pieters、Sabrina Ferhi、Alicia Letaieff、Abel Carlin-Sinclair、Sylvain Marque、Jérome Marrot、Béchir Ben Hassine、Anne Gaucher、Damien Prim

  DOI：10.1016/j.tetlet.2013.06.101

  日期：2013.8

  Synthesis of partially hydrogenated oxa[5]helicenes is described starting from easily available beta-chlorovinylaldehydes. The short sequence involved a Suzuki-Miyaura type coupling between beta-chlorovinylaldehydes and arylboronic acids bearing ortho-methoxy groups. The presence of both the formyl and the methoxy groups allowed after reduction and demethylation respectively, the construction of the central dehydropyran ring. The molecular structure of the extended benzopyrene-based oxa[5]helicenes has been fully determined in solution and in the solid state. The strategy could be extended to oxa[6]helicene. Atroposelective Suzuki-Miyaura couplings were the key steps of the nonracemic preparation of oxa[5]helicenes. Ee observed are in good agreement with the theoretically calculated racemization barriers. (C) 2013 Elsevier Ltd. All rights reserved.
• CAGNIANT M.; KIRSCH G., C. R. ACAD. SCI. <CHDC-AQ>, 1975, C 281, NO 11, 393-395
  作者：CAGNIANT M.、 KIRSCH G.

  DOI：——

  日期：——