苯并(c)吖啶 | 225-51-4

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 苯并(c)吖啶
• 中文别名: 苯并[c]吖啶
• 英文名称: benz[c]acridine
• 英文别名: 3,4-Benzacridin；benzo[c]acridine；Benzacridin；Benzoacridin；benzacridine
• CAS: 225-51-4
• 化学式: C₁₇H₁₁N
• 分子量: 229.281
• InChiKey: OAPPEBNXKAKQGS-UHFFFAOYSA-N

物化性质

• 熔点：
  132°C
• 沸点：
  361.18°C (rough estimate)
• 密度：
  1.1281 (rough estimate)
• 物理描述：
  Benz[c]acridine is a solid.
• 颜色/状态：
  Yellow needles
• 溶解度：
  Very slightly soluble in water
• 蒸汽压力：
  9.8X10-7 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Very stable
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• 解离常数：
  pKa = 4.70
• 保留指数：
  2444;2442.9;392.06;392.11;392.41;392.6;393.41;392.68;392.6;392.5

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

湾区二醇环氧化合物和四氢环氧化合物对细菌（鼠伤寒沙门氏菌）和哺乳动物细胞（中国仓鼠V-79细胞）的诱变作用比非湾区的相应化合物高出1-4个数量级。在所有研究的诱变测试系统中，B(c)AC的湾区二醇环氧化合物和四氢环氧化合物的活性显著高于B(a)AC的类似物和衍生物，这表明N-杂原子的位置对生物活性具有重要性。用Aroclor 1254处理的大鼠肝微粒体的代谢激活研究表明，B(c)Ac 3,4-二氢二醇比B(a)AC 3,4-二氢二醇更容易代谢为诱变产物。B(c)AC的1,2-、5,6-、8,9-和10,11-二氢二醇没有被代谢激活为诱变代谢物。

The bay-region diol epoxides and tetrahydro epoxides of benz(c)acridine were from 1-4 orders of magnitude more mutagenic to bacterial (Salmonella typhimurium) and mammalian cells (Chinese hamster V-79 cells) than were their non-bay-region counterparts. In all the mutagenic test systems studied, the bay-region diol epoxides and tetrahydro epoxides of B(c)AC were substantially more active than the analogs and derivatives of B(a)AC, indicating the importance of the position of N-heteroatom on the biological activity. Metabolic activation studies with hepatic microsomes from Aroclor 1254-treated rats indicated that B(c)Ac 3,4-dihydrodiol was metabolized to mutagenic products to a greater extent than B(a)AC 3,4-dihydrodiol. The 1,2-, 5,6-, 8,9-, and 10,11-dihydrodiol of B(c)AC were not metabolically activated to mutagenic metabolites.

来源:Hazardous Substances Data Bank (HSDB)

代谢

5,6-二氢二醇苯并(c)吖啶已被检测为代谢物，与其他未识别的二氢二醇和单羟基衍生物一起，在将苯并(c)吖啶与大鼠肝脏和肺微粒体制剂孵化的研究中。

The 5,6-dihydrodiol of benz(c)acridine has been detected as a metabolite together with other, unidentified dihydrodiols & monohydroxyderivatives in studies in which benz(c)acridine was incubated with rat liver and lung microsomal preparations.

来源:Hazardous Substances Data Bank (HSDB)

代谢

未经处理、使用苯巴比妥（PB）处理和使用苯并(k)荧蒽（BkF）处理的大鼠肝脏和肺微粒体对苯(a)和苯(c)吖啶的代谢进行了研究，采用气相色谱/质谱（GC/MS）法。发现环氧化和环氧化物水解成二氢二醇是所有底物的主要途径。在苯(c)吖啶的情况下，可能会发生N-氧化。在苯(a)和苯(c)吖啶的情况下，没有获得明确的最终致癌物（t-3,4-二氢二醇-1,2-环氧化物）形成的证据。苯巴比妥诱导了K区氧化，而在苯(c)吖啶的情况下，BkF处理后非K区代谢产物的形成增加。

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats was studied by gas chromatography/mass spectrometry (GC/MS). Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-Oxidation is likely to occur in the case of benz(c)acridine. No unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides) in case of both benz(a)- and benz(c)acridine. K-Region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites increased after BkF treatment in the case of benz(c)acridine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

苯并(a)和苯并(c)吖啶在大鼠肺和肝微粒体中的主要代谢激活途径是氧化成酚和二氢二醇。未经处理的鼠的微粒体中，两种吖啶在K区的氧化占主导地位，并且被苯巴比妥预处理所刺激。苯并(c)吖啶与肺和肝微粒体的代谢表现出相似的行为。即使由苯巴比妥和苯并(K)芘诱导，也没有影响K区与非K区氧化的比率。

The main pathway of the metabolic activation of benz(a)- and benz(c)acridine in rat lung and liver microsomes was oxidation to phenols and dihydrodiols. Oxidation at the K-region predominated in both acridines with microsomes of untreated rats and was stimulated by phenobarbital pretreatment. The benz(c)acridine metabolism with lung and liver microsomes showed a similar behavior. Even induction by phenobarbital and benzo(K)fluoranthene did not influence the ratio between K-region and non-K region oxidation.

来源:Hazardous Substances Data Bank (HSDB)

代谢

未经处理、使用苯巴比妥（PB）处理和使用苯并(k)荧蒽（BkF）处理的大鼠肝脏和肺微粒体对苯(a)和苯(c)吖啶的代谢进行了研究，通过气相色谱/质谱法。发现环氧化和环氧化物的水解成为二氢二醇是所有底物的主要途径。在苯(c)吖啶的情况下，N-氧化可能发生。然而，没有获得明确的证据表明形成了终极致癌物（t-3,4-二氢二醇-1,2-环氧化物）。K区氧化由苯巴比妥诱导，而在苯(c)吖啶的情况下，非K区代谢物的形成在BkF处理后增加。

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats has been studied by gas chromatography/mass spectrometry. Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-oxidation is likely to occur in the case of benz(c)acridine. However, no unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides). K-region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites incr after BkF treatment in the case of benz(c)acridine.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性的证据有限。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：苯并[c]吖啶

IARC Carcinogenic Agent:Benz[c]acridine

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：无法归类其对人类致癌性

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32卷：(1983年) 多环芳烃，第一部分：化学、环境和实验数据 增补第7卷：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） 第103卷：(2013年) 沥青和沥青排放，以及一些N-和S-杂环芳烃

IARC Monographs:Volume 32: (1983) Polynuclear Aromatic Compounds, Part 1: Chemical, Environmental and Experimental Data 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) Volume 103: (2013) Bitumens and Bitumen Emissions, and some N- and S-Heterocyclic Aromatic Hydrocarbons

来源:International Agency for Research on Cancer (IARC)

毒理性

• 相互作用

未经处理、使用苯巴比妥（PB）处理和使用苯并(k)荧蒽（BkF）处理的大鼠肝脏和肺微粒体对苯(a)和苯(c)吖啶的代谢进行了研究，通过气相色谱/质谱法。发现环氧化和环氧化物的水解成为二氢二醇是所有底物的主要途径。在苯(c)吖啶的情况下，N-氧化可能发生。然而，没有获得明确的证据表明形成了终极致癌物（t-3,4-二氢二醇-1,2-环氧化物）。K区氧化由苯巴比妥诱导，而在苯(c)吖啶的情况下，非K区代谢物的形成在BkF处理后增加。

The metabolism of benz(a)- and benz(c)acridine by liver and lung microsomes from untreated, phenobarbital (PB)-treated and benzo(k)fluoranthene (BkF)-treated rats has been studied by gas chromatography/mass spectrometry. Epoxidation and hydrolysis of the epoxides to dihydrodiols were found to be the predominant pathways for all substrates. N-oxidation is likely to occur in the case of benz(c)acridine. However, no unequivocal evidence could be obtained for the formation of the ultimate carcinogens (the t-3,4-dihydrodiol-1,2-epoxides). K-region oxidation was induced by phenobarbital, whereas the formation of non-K-region metabolites incr after BkF treatment in the case of benz(c)acridine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

多核芳烃（PAH）进入细胞和细胞内膜之间的传输机制被讨论。从分配参数来看，限速步骤涉及在磷脂表面的界面水中转移物种的溶剂化。研究了从磷脂酰胆碱囊泡中转移芘的过程。/多核芳烃/

The mechanism of transport by polynuclear aromatic hydrocarbons (PAH) into cells & between intracellular membranes is discussed. From the partitioning parameters, the rate limiting step involves solvation of transfer species in the interfacial water at phospholipid surface. Transfer of pyrene out of the phosphatidylcholine vesicles was examined. /Polynuclear aromatic hydrocarbons/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

多环芳烃在脂肪组织和高脂食品中具有高度溶解性。

Polynuclear aromatic hydrocarbons are highly soluble in adipose tissue and lipids. /Polynuclear aromatic hydrocarbons/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 2811

制备方法与用途

类别：有毒物品

可燃性危险特性

• 可燃；燃烧时会产生有毒氮氧化物烟雾

储运特性

• 通风、低温、干燥环境储存与运输

灭火剂

• 干粉、泡沫、沙土、二氧化碳、雾状水

反应信息

• 作为反应物：
  描述：

  苯并(c)吖啶 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 碘 、 sodium 、 三氯化铁 、 lithium carbonate 、 lithium fluoride 作用下， 以 戊醇 为溶剂， 反应 3.0h， 生成 (+/-)-trans-1,2-Diacetoxy-1,2,3,4-tetrahydrobenzacridine
  参考文献：
  名称：

  Synthesis of dihydrodiol and other derivatives of benz[c]acridine

  摘要：

  DOI：

  10.1021/jo00331a019
• 作为产物：
  描述：

  2-甲基苯胺 盐酸盐 在 lead(II) oxide 作用下， 生成 苯并(c)吖啶
  参考文献：
  名称：

  Ullmann; La Torre, Chemische Berichte, 1904, vol. 37, p. 2924

  摘要：

  DOI：

文献信息

• Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
  作者：Mei-Ling Tan、Shuo Tong、Sheng-Kai Hou、Jingsong You、Mei-Xiang Wang

  DOI：10.1021/acs.orglett.0c01775

  日期：2020.7.17

  catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction

  我们在本文中报道了CuI / DMEDA催化酰胺与各种二（邻-溴芳基）甲烷的N，N-二芳基化反应，以产生各种9,10-二氢ac啶衍生物。在温和条件下选择性氧化所得的9,10-二氢ac啶衍生物，得到afford啶，a啶酮和a啶鎓衍生物。铜催化的N，N-二芳基化反应与氧化芳构化反应相结合，使得能够容易地构建具有不同邻位熔融模式的氮原子嵌入的四碳烯和并五碳烯。还证明了发光特性，特别是融合模式对获得的N-多态荧光发射的影响。
• Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
  作者：Jie Li、Eric Tan、Niklas Keller、Yi-Hung Chen、Peter M. Zehetmaier、Andreas C. Jakowetz、Thomas Bein、Paul Knochel

  DOI：10.1021/jacs.8b11466

  日期：2019.1.9

  The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular

  各种有机锌新戊酸酯与邻氨基苯甲酸酯的反应提供苯胺衍生物，其在酸性条件下环化提供缩合喹啉。使用烯基新戊酸锌、富电子芳基新戊酸锌或杂环新戊酸锌直接产生稠合喹啉，其中几种结构属于新的杂环支架。由于具有最佳的空穴能带排列和大的带隙，这些 N-杂环特别适用于有机发光二极管，因为它们具有高光致发光量子产率和长激子寿命，以及甲基铵碘化铅钙钛矿太阳能电池中的空穴传输材料.
• Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
  作者：Aleksandr N. Shestakov、Alena S. Pankova、Mikhail A. Kuznetsov

  DOI：10.1007/s10593-017-2179-5

  日期：2017.10

  Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Brønsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently

  3-炔基-2-芳基吡啶和喹啉的环异构化为苯并[ h ]喹啉和苯并[ c ] -ac啶提供了一种直接的方法。在三键处的取代基决定过渡金属催化或布朗斯台德酸催化之间的选择。三氟甲磺酸的直接亲电子活化引起邻-芳基（苯基乙炔基）片段的几乎定量环化。PtCl 2有效催化2-芳基-3-乙炔基戊烯的环化。
• Über aromatenkomplexe von metallen CVIII. Chrom-tricarbonyl-komplexe kondensierter aromaten mit heteroatomen
  作者：E.O. Fischer、H.A. Goodwin、C.G. Kreiter、H.D. Simmons、K. Sonogashira、S.B. Wild

  DOI：10.1016/s0022-328x(00)87676-7

  日期：1968.10

  The chromium tricarbonyl complexes with the condensed heterocycles benzofuran, dibenzofuran, benzo [b] naphtho [2,3-d] furan, benzo [b] thiophene, dibenzothiophene, benzo [b] naphtho [2,1-d] thiophene, indole, carbazole, benzo [h] quinoline, benzo [f] quinoline and benzo [a] acridine have been prepared for the first time. The structures of the complexes were determined by analysis of their 1H NMR spectra

  三羰基铬铬与稠合杂环苯并呋喃，二苯并呋喃，苯并[ b ]萘[2,3- d ]呋喃，苯并[ b ]噻吩，二苯并噻吩，苯并[ b ]萘[2,1- d ]噻吩，吲哚，首次制备了咔唑，苯并[ h ]喹啉，苯并[ f ]喹啉和苯并[ a ] a啶。配合物的结构通过分析其1 H NMR光谱来确定。
• Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[ <i>h</i> ]quinolines with 1‐Diazonaphthoquinones
  作者：Chongqing Pan、Si‐Yong Yin、Shao‐Bo Wang、Qing Gu、Shu‐Li You

  DOI：10.1002/anie.202103638

  日期：2021.7.5

  functionalization reactions have witnessed a significant progress in organic synthesis. In sharp contrast, the reported chiral Cp ligands are limited to C-linked Cp and are often synthetically challenging. To address these issues, we have developed a novel class of tunable chiral cyclopentadienyl ligands bearing oxygen linkers, which were efficient catalysts for C−H arylation of benzo[h]quinolines with

  手性环戊二烯基铑 (CpRh) 络合物催化的不对称 CH 官能化反应在有机合成中取得了重大进展。与此形成鲜明对比的是，报道的手性 Cp 配体仅限于 C-连接的 Cp，并且通常在合成上具有挑战性。为了解决这些问题，我们开发了一类新型的带有氧接头的可调谐手性环戊二烯基配体，它们是苯并 [ h ] 喹啉与 1-重氮萘醌的C-H 芳基化的有效催化剂，以优异的产率和对映选择性提供轴向手性杂二芳基（高达 99% 的产率，98.5:1.5 er）。机理研究表明，该反应可能通过亲电 C-H 活化进行，然后是环金属化铑 (III) 配合物与 1-重氮萘醌的偶联。

表征谱图