9,10-二乙基菲 | 15810-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 9,10-二乙基菲
• 英文名称: 9,10-diethylphenanthrene
• 英文别名: 9,10-Diaethyl-phenanthren
• CAS: 15810-14-7
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: JURXVMQHSBALPL-UHFFFAOYSA-N

物化性质

• 保留指数：
  367.7;367.97;367.97

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  9,10-二乙基菲 在 吡啶 、 四氧化锇 、 苯 作用下， 生成 9,10-diethyl-9,10-dihydro-phenanthrene-9r,10c-diol
  参考文献：
  名称：

  Criegee et al., Justus Liebigs Annalen der Chemie, 1956, vol. 599, p. 81,93

  摘要：

  DOI：
• 作为产物：
  描述：

  菲 在 溴 作用下， 以 乙醚 、 正己烷 、 溶剂黄146 为溶剂， 生成 9,10-二乙基菲
  参考文献：
  名称：

  Metal-ammonia reduction. VII. Stereospecific reduction in the phenanthrene series

  摘要：

  DOI：

  10.1021/jo00826a007

文献信息

• Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp²)–H Arylation, Cyclization, and Migration Tandem Reaction
  作者：Bo-Bo Gou、Hui Yang、Huai-Ri Sun、Jie Chen、Junliang Wu、Ling Zhou

  DOI：10.1021/acs.orglett.8b03511

  日期：2019.1.4

  routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)–H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized

  菲是化学和材料科学中的重要结构基序，并且已经开发出许多合成途径来构建其骨架。然而，不对称菲的合成仍然是一个挑战。在这里，开发了一种有效的一锅串联反应，用于通过顺序的γ-C（sp 2）-H芳基化，阳离子环化，脱水和1,2-迁移制备菲。合成了具有多种官能团的多种对称和不对称菲，收率良好。
• Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium-Catalyzed Annulation of Ring-Fused Benzocyclobutenol with Alkyne through C−C Bond Cleavage
  作者：Jiajia Yu、Hong Yan、Chen Zhu

  DOI：10.1002/anie.201509973

  日期：2016.1.18

  iridium‐catalyzed intermolecular cyclization between alkynes and ring‐fused benzocyclobutenols (RBCB) through C−C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. This procedure provides a unique and expeditious tool for the synthesis of PAHs.

  描述了炔烃和环稠合苯并环丁烯醇（RBCB）之间通过C-C键断裂进行的第一个铱催化的分子间环化反应。在温和的条件下以高收率获得了多种具有多个取代基的难以捉摸的多环芳烃（PAH）。该程序为合成多环芳烃提供了独特而快捷的工具。
• Unprecedented reductive dealkoxylation of aryl alkyl ethers and intramolecular C–C coupling of 2,2′-dialkoxystilbenes with low valent titanium: one-pot synthesis of phenanthrenes
  作者：Asoke Banerji、Sandip K. Nayak

  DOI：10.1039/c39910001432

  日期：——

  Facile dealkoxylation of aryl alkyl ethers has been carried out using TiCl3–Li–THF (tetrahydrofuran); a novel one-pot synthesis of phenanthrenes from ortho-alkoxyaromatic aldehydes/ketones is described.

  使用TiCl3-Li-THF（四氢呋喃）可以轻松完成芳基烷基醚的脱烷氧基化反应；描述了一种从邻烷氧基芳香醛/酮的新的单锅合成菲的方法。
• Nitration of 9,10-Dialkylphenanthrenes. Side-chain Nitrooxylation in Competition with Side-chain Nitration
  作者：Hitomi Suzuki、Hajime Yoneda、Terukiyo Hanafusa

  DOI：10.1246/bcsj.48.2116

  日期：1975.7

  9,10-Dimethylphenanthrene and 9-methyl-10-ethylphenanthrene gave 9-methyl-10-nitromethylphenanthrene and 9-ethyl-10-nitromethylphenanthrene, respectively, as major product, when treated with fuming nitric acid in dichloromethane at low temperatures. In contrast, 9,10-diethylphenanthrene yielded a comparable mixture of products arising from side-chain nitration and side-chain nitrooxylation, which on chromatography over deactivated alumina gave 9-ethyl-10-(α-nitroethyl)phenanthrene and 9-ethyl-10-(α-hydroxyethyl)phenanthrene as main isolable products. 9-Methylphenanthrene and 9-ethylphenanthrene were both simply nitrated at the ring position to give the corresponding 9-alkyl-10-nitrophenanthrenes in good yields. No side-chain attack was observed. Factors responsible for determining which one of the competitive pathways will be followed have been discussed.

  9,10-二甲基菲和9-甲基-10-乙基菲在低温下与溶于二氯甲烷的浓硝酸反应时，主要产物分别为9-甲基-10-硝基甲基菲和9-乙基-10-硝基甲基菲。相比之下，9,10-二乙基菲产生了由侧链硝化和侧链硝氧化反应生成的类似产物混合物，在用脱活铝土矿进行色谱分离时，得到的主要可分离产物为9-乙基-10-(α-硝基乙基)菲和9-乙基-10-(α-羟基乙基)菲。9-甲基菲和9-乙基菲也仅在环的位置进行硝化，得到相应的9-烷基-10-硝基菲，产率良好。未观察到侧链攻击。文中讨论了影响选择竞争反应路径的因素。
• Highly active salted low-valent titanium reagents for various SET induced reactions
  作者：Shyam Rele、Subrata Chattopadhyay、Sandip K Nayak

  DOI：10.1016/s0040-4039(01)02009-3

  日期：2001.12

  External addition of inorganic salts (Group I and II metal halides) to the preformed low-valent titanium reagent A (TiCl3–Li–THF) dramatically enhanced its activity. The new reagents were used to carry out various SET reactions including McMurry's olefination at a faster rate even at ambient temperature.

  在预先形成的低价钛试剂A（TiCl 3 –Li–THF）中外部添加无机盐（I和II类金属卤化物）可显着增强其活性。新试剂用于甚至在环境温度下也能以更快的速率进行各种SET反应，包括McMurry的烯化反应。