1-methyl-1,2,3,4-tetrahydro-4-phenanthrone | 97278-01-8

• 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: 1-methyl-1,2,3,4-tetrahydro-4-phenanthrone
• 英文别名: 1-methyl-4-oxo-1,2,3,4-tetrahydrophenanthrene；1-methyl-2,3-dihydro-1H-phenanthren-4-one；1-Methyl-2,3-dihydro-1H-phenanthren-4-on；1-methyl-2,3-dihydro-1H-phenanthren-4-one
• CAS: 97278-01-8
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: ZQSXXCPVSRVTAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  145 °C(Press: 0.4 Torr)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-methyl-1,2,3,4-tetrahydro-4-phenanthrone 在 氢氧化钾 、 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 47.0h， 生成 (+/-)-trans-4-(3,5-dinitrobenzamido)-1-methyl-1,2,3,4-tetrahydrophenanthrene
  参考文献：
  名称：

  Conformational effects on the enantioselective recognition of 4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene derivatives by a Naproxen-derived chiral stationary phase

  摘要：

  4-(3,5-Dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene and derivatives having methyl groups in various positions on the tetrahydro ring were synthesized and resolved on an (S)-Naproxen-derived chiral stationary phase. The difference in the Gibbs free energy, DeltaDeltaG, of the transient diastereomeric adsorbates was determined from the chromatographic data. The highest enantioselectivity was observed for cis-4-(3,5-dinitrobenzamido)-3-methyl-1,2,3,4-tetrahydrophenanthrene. Introducing methyl groups into other positions of the tetrahydrophenanthrene ring proved to be detrimental to enantioselectivity. Prior studies indicate that, in the 4-(3,5-dinitrobenzamido)1,2,3,4-tetrahydrophenanthrene used in the Whelk-O chiral HPLC columns, the 3,5-dinitrobenzamide group occupies a pseudoaxial position, thus forming one wall of a binding cleft owing to its spatial relationship with the naphthyl portion of the selector. The effect of the methyl substituents on enantioselectivity is attributed to their ability to both influence the 'psuedoaxiality' of the dinitrobenzamido group and to their ability to sterically hinder the presentation of the 'back face' of this group to the Naproxen-derived selector. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00307-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氟酸 作用下， 生成 1-methyl-1,2,3,4-tetrahydro-4-phenanthrone
  参考文献：
  名称：

  Johnson; Johnson; Petersen, Journal of the American Chemical Society, 1945, vol. 67, p. 1360,1364

  摘要：

  DOI：

文献信息

• Annulative π‐Extension by Rhodium(III)‐Catalyzed Ketone‐Directed C−H Activation: Rapid Access to Pyrenes and Related Polycyclic Aromatic Hydrocarbons (PAHs)
  作者：Md Raja Sk、Arya Bhattacharyya、Shuvendu Saha、Arpita Brahma、Modhu Sudan Maji

  DOI：10.1002/anie.202305258

  日期：2023.7.24

  An annulative π-extension (APEX) method is reported to build a benzene ring at the masked bay-region of polycyclic aromatic hydrocarbons (PAHs) under RhIII-catalysis. This one-pot, ketone-directed C−H activation/annulation reaction between a ketone and an alkyne selectively provides challenging 4,5-disubstituted pyrenes, and optically pure bipyrene derivatives.

  据报道，环形 π 延伸 (APEX) 方法可在 Rh III催化下在多环芳烃 (PAH) 的掩蔽湾区构建苯环。酮和炔之间的这一一锅、酮导向的 C−H 活化/成环反应选择性地提供了具有挑战性的 4,5-二取代芘和光学纯的联芘衍生物。
• REACTIONS OF 1,2,3,4-TETRAHYDROPHENANTHRENE AND DERIVATIVES. VI. COMPOUNDS DERIVED FROM 1-METHYLTETRAHYDROPHENANTHRENE
  作者：W. E. BACHMANN、R. F. EDGERTON

  DOI：10.1021/jo01151a032

  日期：1950.9
• Friedel-Crafts Reaction Involving Unsaturated Ketones and Esters. I. New syntheses of 1-Methyl-1,4-Dimethyl-, and 9-Methyl-Phenanthrene
  作者：S. M. Mukherji、N. K. Bhattacharyya

  DOI：10.1021/jo50009a004

  日期：1952.9
• Carbon-13 magnetic resonance of hydroaromatics. 3. Conformation of 1,2,3,4-tetrahydrophenanthrene and 9,10-dihydrophenanthrene and their methyl derivatives
  作者：Frederick G. Morin、Walter J. Horton、David M. Grant、Ronald J. Pugmire、Don K. Dalling

  DOI：10.1021/jo00218a027

  日期：1985.9