1,4-二甲基菲 | 22349-59-3

• 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: 1,4-二甲基菲
• 英文名称: 1,4-dimethylphenanthrene
• 英文别名: 1,4-Dimethyl-phenanthren
• CAS: 22349-59-3
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: DWMAJXVIIUYYOH-UHFFFAOYSA-N

物化性质

• 熔点：
  50.4°C
• 沸点：
  370.14°C (rough estimate)
• 密度：
  1.0426 (estimate)
• 保留指数：
  344.09;344
• 稳定性/保质期：
  存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 致癌物分类

国际癌症研究机构致癌物：1,4-二甲基菲

IARC Carcinogenic Agent:1,4-Dimethylphenanthrene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第7卷补充：致癌性的总体评估：更新国际癌症研究机构专著第1至42卷，1987年；440页；ISBN 92-832-1411-0（已绝版）

IARC Monographs:Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

来源:International Agency for Research on Cancer (IARC)

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  1,4-二甲基菲 在 异戊醇 、 sodium 作用下， 生成 1,4-dimethyl-phenanthrene-9,10-dione
  参考文献：
  名称：

  Mutation in Arabidopsis HIT1 locus causing heat and osmotic hypersensitivity

  摘要：

  A mutant strain of Arabidopsis thaliana var. Columbia whose seedling development was 2 to 3 degreesC more sensitive to high temperature inhibition than wild type was isolated. This mutant (hit1, for heat-intolerant) did not show any phenotypic change when grown at 22 degreesC. However, incubation at 37 degreesC for 4 days was determined to be lethal for the mutant but not for wild-type plants. Leaves of wild type respond to high temperature by becoming erect, but by comparison leaves of the hit1 mutant remain horizontal and show a slightly wilty appearance. Furthermore, seedling development in hit1 mutants was more sensitive to osmotic stress imposed by exogenous mannitol (>300 mmol/L). These data imply that HIT1 may be responsible for water status regulation by which plants survive heat stress. Genetic analysis shows that the hit1 phenotype is conditioned by a single recessive, nuclear mutation, and the HIT1 locus was closely linked to the nga280 microsatellite marker on chromosome 1.

  DOI：

  10.1016/s0176-1617(00)80110-8
• 作为产物：
  描述：

  2,5-dimethylphenylmagnesium bromide 在 氢氧化钾 、 硫酸 、 氢氟酸 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 生成 1,4-二甲基菲
  参考文献：
  名称：

  263. 2-芳基-环己基乙酸分子内环化的立体方面。第二部分

  摘要：

  DOI：

  10.1039/jr9650001495

文献信息

• Straightforward synthesis of phenanthrenes from styrenes and arenes
  作者：Hu Li、Ke-Han He、Jia Liu、Bi-Qin Wang、Ke-Qing Zhao、Ping Hu、Zhang-Jie Shi

  DOI：10.1039/c2cc33100d

  日期：——

  Semi-one-pot synthesis of phenanthrenes from styrenes and arenes was developed through cross-dehydrogenative coupling. A sequence of Heck-type coupling and photo-cyclization were involved and a variety of functionalities were tolerated. This method provides an effective and practical protocol towards the synthesis of substituted phenanthrenes.

  通过交叉脱氢偶合，从苯乙烯和芳烃半一锅合成菲。涉及一系列的Heck型偶联和光环化，并且可以耐受多种功能。该方法为合成取代的菲提供了有效而实用的方案。
• Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes
  作者：Masahito Murai、Takuya Ogita、Kazuhiko Takai

  DOI：10.1039/c9cc00270g

  日期：——

  Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at

  氧or催化剂与亚磷酸三苯酯作为氧受体的组合使用可以使氧双环二烯高效脱氧芳构化。反应在中性条件下进行并与各种官能团相容。将该脱氧与区域选择性溴化结合，并用呋喃捕获生成的芳烃，导致PAHs的苯环π延伸。这使得可以直接使用未官能化的PAH来扩展π共轭。转变的迭代一次增加了一个稠合苯环的数量，这有可能通过微调π共轭度，形状和边缘拓扑来改变PAHs的性质。
• α-Oxoketene dithioacetal mediated aromatic annulation: highly efficient and concise synthetic routes to potentially carcinogenic polycyclic aromatic hydrocarbons
  作者：Sukumar Nandi、Kausik Panda、J.R Suresh、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/j.tet.2004.02.053

  日期：2004.4

  Highly efficient regiospecific routes to potentially carcinogenic polycyclic aromatic hydrocarbons such as substituted benzo[c]phenanthrenes, benzo[c]fluorenes, 16,17-dihydro-11-methyl-15[H]cyclopenta[a]phenanthrene, 5-methyl-7,8,9,10-tetrahydrochrysene and 1,4-dimethylphenanthrene have been developed. The overall strategy involves our aromatic annulation protocol through base induced conjugate addition–elimination

  高效的区域特异性途径转化为潜在的致癌多环芳烃，例如取代的苯并[ c ]菲，苯并[ c ]芴，16,17-二氢-11-甲基-15 [ H ]环戊[ a ]菲，5-甲基-7已经开发了8，9，10-四氢丙烯和1，4-二甲基菲。总体策略涉及我们的芳族环化方案，即通过碱诱导的共轭加成反应-在环和无环α-氧杂环丁烯二硫缩醛上用适当的芳基乙腈消除，然后酸诱导所得的共轭加合物进行环脱水。随后环化产物的还原性脱硫甲基化（阮内镍）和脱氢（DDQ）以高收率提供了甲基取代的PAH。
• Synthesis of 1,4-, 2,4-, and 3,4-dimethylphenanthrenes: a novel deoxygenation of arene 1,4-endoxides with trimethylsilyl iodide
  作者：Kee Yong Jung、Masato Koreeda

  DOI：10.1021/jo00285a011

  日期：1989.11
• 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