2-chloro-6-(4-methoxy-phenylthio)-benzonitrile | 101339-45-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-chloro-6-(4-methoxy-phenylthio)-benzonitrile
• 英文别名: 2-chloro-6-(p-methoxybenzenethio)benzonitrile；Benzonitrile, 2-chloro-6-[(4-methoxyphenyl)thio]-；2-chloro-6-(4-methoxyphenyl)sulfanylbenzonitrile
• CAS: 101339-45-1
• 化学式: C₁₄H₁₀ClNOS
• mdl: MFCD17020379
• 分子量: 275.759
• InChiKey: VXZOUPKMCSHHBI-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(4-methoxy-phenylthio)-benzonitrile 在 氢氧化钾 、 三氟甲磺酸 作用下， 以 吡啶 为溶剂， 反应 51.0h， 生成 1-<<2-(dimethylamino)ethyl>amino>-7-methoxy-9H-thioxanthen-9-one
  参考文献：
  名称：

  庚酮及其某些同类物的制备及其抗血吸虫和抗肿瘤活性。庚酮作用方式的证据。

  摘要：

  报道了一系列庚烷酮和7-羟基庚酮的酯的合成，它们的抗肿瘤活性以及它们对HC敏感和HC抵抗性血吸虫的抗血吸虫作用。使用tri标记的HC和庚酮N-甲基氨基甲酸酯（HNMC）与小牛胸腺DNA的结合研究提供了证据，表明HNMC而非HC使DNA烷基化。ti化的HNMC还与暴露于药物的完整HeLa细胞的DNA结合，而在相同条件下，极少的tri化的HC与DNA结合。如方案一所示，先前提出的解释HC的抗血吸虫作用的机制，即药物酯化然后DNA烷基化，也适用于药物的抗肿瘤作用。

  DOI：

  10.1021/jm00396a040
• 作为产物：
  描述：

  2-氯-6-硝基苯甲腈 、 4-甲氧基苯硫酚 在 potassium fluoride on basic alumina 、 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以82%的产率得到2-chloro-6-(4-methoxy-phenylthio)-benzonitrile
  参考文献：
  名称：

  Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹

  摘要：

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.

  DOI：

  10.1021/jo980800g

文献信息

• 7-Hydroxylucanthone, 7-hydroxhycanthone and their analogs
  申请人：Rensselaer Polytechnic Institute

  公开号：US04539412A1

  公开（公告）日：1985-09-03

  7-Hydroxylucanthone and 7-hydroxyhycanthone derivatives have been found to have significant antitumor effect. The derivatives are of the general formula: ##STR1## wherein the radicals R.sup.1 and R.sup.2 are lower alkyl groups or other simple groups and R.sup.3 is OH where X.dbd.O, and H or OH where X.dbd.S.

  7-羟基卢坎通和7-羟基海坎通衍生物已被发现具有显著的抗肿瘤效果。这些衍生物的一般化学式为：其中基团R.sup.1和R.sup.2为较低的烷基基团或其他简单基团，R.sup.3为OH，其中X=dbd.O，以及X=dbd.S时为H或OH。
• An Improved Synthetic Method of 1-Chloro-7-methoxy-9<i>H</i>-thioxanthen-9-one
  作者：Hua-Zhong He、Chul-Hoon Kwon

  DOI：10.1081/scc-120021832

  日期：2003.1.8

  1-Chloro-7-methoxy-9H-thioxanthen-9-one (3) was prepared via cyclization of 2-chloro-6-(4-methoxyphenylthio)-benzonitrile (1) in a one pot, two step reaction with improved yield (60%) over the previous literature report.
• ARCHER, SYDNEY;PICA-MATTOCCIA, LIVIA;CIOLI, DONATO;SEYED-MOZAFFARI, AHMAD+, J. MED. CHEM., 31,(1988) N 1, 254-260
  作者：ARCHER, SYDNEY、PICA-MATTOCCIA, LIVIA、CIOLI, DONATO、SEYED-MOZAFFARI, AHMAD+

  DOI：——

  日期：——
• US4539412A
  申请人：——

  公开号：US4539412A

  公开（公告）日：1985-09-03
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.