2,7,9,10-tetramethylphenanthrene | 138200-35-8

• 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: 2,7,9,10-tetramethylphenanthrene
• 英文别名: Phenanthrene, 2,7,9,10-tetramethyl-
• CAS: 138200-35-8
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: UIBRLEYHWHOCFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  0
• 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

反应信息

• 作为产物：
  描述：

  1-(2-甲氧基-5-甲基苯基)乙酮 在 titanium(III) chloride 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到2,7,9,10-tetramethylphenanthrene
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/c39910001432

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。
• 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。
• Dramatic Influence of Nitrogen Heterocycles on the Activity of Low-Valent Titanium Reagent: An Improved One-Pot Synthesis of Phenanthrenes
  作者：Suresh M Kadam、Sandip K. Nayak、Asoke Banerji

  DOI：10.1080/00397919508010799

  日期：1995.1

  A novel low-valent titanium (LVT) induced one-pot synthesis of phenanthrenes (25-38% yield) from ortho-alkoxy aromatic aldehydes/ketones was reported by us earlier. Activity of LVT complex could be modulated rationally by using catalytic amount of pyridine. Use of this LVT-pyridine reagent system improved the yields of phenanthrenes (3) by two folds.