7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one | 14427-61-3

• 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: 7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one
• 英文别名: 7-Methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-on；1(2H)-Phenanthrenone, 3,4,9,10-tetrahydro-7-methoxy-；7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one
• CAS: 14427-61-3
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: FQSUSXXSHPWBMR-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  355.2±31.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one 在 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 N'-[2-(3,3-Dimethoxy-propyl)-7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-(1E)-ylidene]-N,N-dimethyl-hydrazine
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of Two Azatetrahydrochrysenes as Potential Fluorescent Ligands for the Estrogen Receptor

  摘要：

  In an effort to improve upon the spectroscopic characteristics of donor-acceptor tetrahydrochrysene systems that we have previously prepared as fluorescent ligands for the estrogen receptor, we have synthesized two aza analogs as receptor ligand prototypes and characterized their absorbance and fluorescence spectra. 1-Aza-9-hydroxy-5,6,11,12-tetrahydrochrysene (4) and 1,3-diaza-9-hydroxy-5,6,11,12-tetrahydrochrysene (5) were prepared by convenient heterocyclization reactions on a known tricyclic ketone (6). The UV spectra of these heterocycles were quite insensitive to solvent polarity but showed marked red shifts under acidic or basic conditions. These heterocycles displayed complex fluorescence spectra, with emission bands around 400 nm in aprotic medium that shifted to longer wavelength in protic solvents. In many cases, acid and base caused strong red shifts in the emission, with large alterations in quantum yield; in some cases emission bands were shifted as far as 600 nm and dual-emission peaks were observed. Thus, these two azatetrahydrochrysenes show greater environmental sensitivity-especially to changes in pH-than do our previously described donor-acceptor tetrahydrochrysenes. The binding affinity of these ligand prototypes for the estrogen receptor, however, is low, indicating that other structure modifications will be required to make them useful fluorescent ligands for this receptor.

  DOI：

  10.1021/jo9708405
• 作为产物：
  描述：

  4-(6-methoxy-3,4-dihydro-2H-naphthylidene-(1ξ))-trans-crotonic acid methyl ester 在 乙醇 、 aged Raney nickel 、 乙酸酐 、 溶剂黄146 、 zinc(II) chloride 作用下， 生成 7-methoxy-3,4,9,10-tetrahydro-2H-phenanthren-1-one
  参考文献：
  名称：

  Selective Raney Nickel Hydrogenation of Methyl γ-(6-Methoxy-1,2,3,4-Tetrahydro-1-Paphthylidene)-Crotonate. Synthesis of 1-Keto-7-Methoxy-1,2,3,4,9,10-Hexahydrophenanthrene

  摘要：

  DOI：

  10.1021/jo50017a019

文献信息

• Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a- hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement.
  作者：Neeraj Garg、Adolf Gogoll、Christer Westerlund、Staffan Sundell、Anders Karlén、Anders Hallberg

  DOI：10.1016/s0040-4020(96)00927-1

  日期：1996.11

  The preparation of cis-1α-acetoxy-7-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)- phenanthrenone 5 was accomplished starting from 6-methoxy-1-tetralone. Reduction of 7-methoxy-1,2,3, 4,9,10-hexahydro-1-oxo-phenanthrene 8, acetylation and subsequent oxidation delivered 5. Application of an analogus procedure to the preparation of cis-1β-acetoxy-5-methoxy-1,2,3,4,,4a,10a-hexahydro-9(10H)- phenanthrenone 6

  从6-甲氧基-1-四氢萘酮开始，完成了cis-1α-乙酰氧基-7-甲氧基-1,2,3,4,4a，10a-六氢-9（10H）-菲咯酮5的制备。还原7-甲氧基-1,2,3,4,9,10-六氢-1-氧代菲8，乙酰化和随后的氧化5。将类比方法应用于制备顺式1β-乙酰氧基-5-甲氧基-1,2,3,4，，4a，10a-六氢-9（10H）-菲咯酮6是不可行的。开发了一种更精细的化合物6合成路线，其中涉及1,2-烷基移位重排的环氧-芳烃反应构成了高度选择性的键转化。
• The Total Synthesis of Estrone and Three Stereoisomers Including Lumiestrone
  作者：William S. Johnson、D. K. Banerjee、William P. Schneider、C. David Gutsche、Wesley E. Shelberg、Leland J. Chinn

  DOI：10.1021/ja01131a037

  日期：1952.6
• 12. The synthesis of compounds related to the sterols, bile acids, and oestrus-producing hormones. Part VIII
  作者：C. L. Hewett

  DOI：10.1039/jr9360000050

  日期：——
• Cyclisation photochimique d'alkyl-2 aryl-3 cyclohexène-2 ones
  作者：Yves Fort、Jean-Pierre Pete

  DOI：10.1016/s0040-4039(00)99843-5

  日期：1984.1
• Photochemical cyclization of 2-alkyl-3-aryl-2-cyclohexenones and 2-alkoxy-3-aryl-2-cyclohexenones
  作者：Alexandre Feigenbaum、Yves Fort、Jean Pierre Pete、Denise Scholler

  DOI：10.1021/jo00373a015

  日期：1986.11