1-氯甲基-5-硝基萘 | 6625-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-氯甲基-5-硝基萘
• 英文名称: 1-(chlorometyl)-5-nitronaphthalene
• 英文别名: 1-Nitro-5-chlormethyl-naphthalin；5-nitro-1-chloromethylnaphthalene；5-nitro-1-naphthylmethyl chloride；1-chloromethyl-5-nitro-naphthalene；1-Chlormethyl-5-nitro-naphthalin；1-(chloromethyl)-5-nitronaphthalene
• CAS: 6625-54-3
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: PHZIJSANQGZNPP-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  376.5±22.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  1-氯甲基-5-硝基萘 在 钯 、 丙酮 作用下， 生成 1-氨基-5-甲基萘
  参考文献：
  名称：

  Bardhan et al., Journal of the Chemical Society, 1957, p. 921

  摘要：

  DOI：
• 作为产物：
  描述：

  (氯甲基)萘 在 硝酸 、 乙酸酐 作用下， 生成 1-氯甲基-5-硝基萘
  参考文献：
  名称：

  Ismail'skii; Kosin, Doklady Akademii Nauk SSSR, 1940, vol. 28, p. 622,624

  摘要：

  DOI：

文献信息

• Hypoxia-Selective Antitumor Agents. 12. Nitrobenzyl Quaternary Salts as Bioreductive Prodrugs of the Alkylating Agent Mechlorethamine
  作者：Moana Tercel、William R. Wilson、Robert F. Anderson、William A. Denny

  DOI：10.1021/jm9507791

  日期：1996.1.1

  -358 mV and undergoes reductively-induced fragmentation to release the nitrogen mustard mechlorethamine. The compounds were prepared by halogenation (SOCl2) of the corresponding quaternary diols, which in turn were synthesized from N-methyldiethalnolamine and substituted nitrobenzyl chlorides. The reduction potentials of the benzene-substituted compounds were generally well-predicted by Hammett substituent

  新型低氧选择性细胞毒素N，N-双（2-氯乙基）-N-甲基-N-（2-硝基苄基）氯化铵（3a）的一系列苯取代类似物，以及三个相应的“环”四氢异喹啉鎓已经制备了类似物21a-23a和两种萘衍生物（19a和20a），并在有氧和低氧条件下评估了培养的哺乳动物肿瘤细胞的细胞毒性。母体化合物3a的单电子还原电势为-358mV，并经历还原诱导的裂解以释放芥菜甲氧乙胺氮。该化合物是通过相应的季二醇的卤化（SOCl2）制备的，而这些季二醇又是由N-甲基二乙二胺和取代的硝基苄基氯合成的。苯取代的化合物的还原电势通常通过哈米特取代基关系很好地预测。所有化合物对修复缺陷型UV4细胞的毒性都比相应的野生型AA8细胞高得多，这是预期的，如果活性细胞毒性物质用作DNA烷基化剂。与AA8相比，它们对人细胞EMT6和FME的毒性更大，但其原因尚不清楚。在苯环中被给电子取代基取代的3a类似物为低氧AA8细胞提供了广泛不同的选
• Nitrobenzyl mustard quaternary salts and their use as hypoxia-selective
  申请人：Auckland UniServices Limited

  公开号：US05691371A1

  公开（公告）日：1997-11-25

  Nitrobenzyl mustard quaternary salts of formula (I), ##STR1## and the pharmaceutically acceptable salts thereof, process for their manufacture and their chemotherapeutic use as hypoxia selective cytotoxic agents. Wherein, X represents a linker chain --CR.sub.1 R.sub.2 -- or CR.sub.1 .dbd.CR.sub.2-- (where R.sub.1 and R.sub.2 are separately H, lower alkyl, phenyl or nitrophenyl; Y is halogen or OSO.sub.2 R; Q is lower alkyl (optionaly substituted with alkyl and/or ether groups and containing up to 6 carbons) or nitrophenyl; Ar represents a mono- or bicyclic aromatic unit, R is lower alkyl optionally substituted with alkyl and/or other groups, and may contain up to eight carbon atoms. Z represents one or more of the groups NO.sub.2, SO.sub.2 R, CONHR, R, OR, SR, CF.sub.3 and aza (ring --CH.dbd.replaced by --N.dbd.); with the proviso that when H-Cl or Br, Q=Me, and X=CH.sub.2 -- then Ar.noteq.2-nitrophenyl or 4-nitrophenyl.

  硝基苄芥基芥基季铵盐的化学式(I)，及其药用可接受盐，其制备方法以及作为低氧选择性细胞毒性剂的化疗用途。其中，X代表一个连接链--CR.sub.1 R.sub.2--或CR.sub.1.dbd.CR.sub.2--（其中R.sub.1和R.sub.2分别为H、较低烷基、苯基或硝基苯基；Y为卤素或OSO.sub.2 R；Q为较低烷基（可选择地与烷基和/或醚基替代并含有最多6个碳）或硝基苯基；Ar代表一个单环或双环芳香单元，R为较低烷基，可选择地与烷基和/或其他基团替代，并且可能含有多达八个碳原子。Z代表NO.sub.2、SO.sub.2 R、CONHR、R、OR、SR、CF.sub.3和氮代（环--CH.dbd.被--N.dbd.替换）中的一个或多个基团；但当H-Cl或Br，Q=Me，X=CH.sub.2时，Ar.noteq.2-硝基苯基或4-硝基苯基。
• Azo dyestuff intermediate nitro- or aminobenzenes ring-substituted by a
  申请人：Sterling Drug Inc.

  公开号：US04146558A1

  公开（公告）日：1979-03-27

  Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge. K is a small integer whose value is dependent on the nature of A such that it has a range from one to two; R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ; R.sup.10 is lower-alkyl or lower-alkenyl; A.sup.1 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; G is a small integer whose value is dependent on the nature of A.sup.1 such that it has a range from one to two; R.sup.8 ' is lower-alkyl; R.sup.9 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.10 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl or R.sup.9 ' and R.sup.10 ' together with the nitrogen atom are morpholino; A.sup.2 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; h is a small integer whose value is dependent on the nature of A.sup.2 such that it has a range from one to two; and An is an anion are particularly useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials. These dyes dye cotton and paper various shades of stable yellows, reds and oranges. The dyeing from these dyes on paper are less prone to bleed and have a high degree of color discharge when bleached with hypochlorite or chlorine bleaches.

  水溶性阳离子染料的化学式为##STR1## 其中R.sup.0为氢、较低烷基或羟基较低烷基；R.sup.1为较低烷基、较低烯烃基或羟基较低烷基；R.sup.2为较低烷基、较低烯烃基、羟基较低烷基或-(较低烷基)-NR.sup.0 Y或R.sup.1和R.sup.2与氮原子一起，为吡咯烷基、哌啶基或4-较低酰基哌嗪基；Y为氢或##STR2## 其中R为氢、较低烷基、较低烯烃基、苯基或苯基较低烷基；A为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子。K是一个小整数，其值取决于A的性质，范围为一到二；R.sup.8为较低烷基、较低烯烃基或羟基较低烷基；R.sup.9为较低烷基、羟基较低烷基或NH.sub.2；R.sup.10为较低烷基或较低烯烃基；A.sup.1为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；G是一个小整数，其值取决于A.sup.1的性质，范围为一到二；R.sup.8 '为较低烷基；R.sup.9 '为较低烷基、较低烯烃基或羟基较低烷基；R.sup.10 '为较低烷基、较低烯烃基或羟基较低烷基或R.sup.9 '和R.sup.10 '与氮原子一起为吗啉基；A.sup.2为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；h是一个小整数，其值取决于A.sup.2的性质，范围为一到二；An为阴离子，特别适用于染色天然纤维、合成纤维形成材料和纤维素材料。这些染料可使棉花和纸张呈现各种稳定的黄色、红色和橙色。这些染料在纸张上的染色不易渗出，漂白时与次氯酸盐或氯漂白剂一起具有高度的色彩释放度。
• Intramolecular electron transfer and dehalogenation of nitroaromatic anion radicals
  作者：J. P. Bays、S. T. Blumer、S. Baral-Tosh、D. Behar、P. Netav

  DOI：10.1021/ja00341a003

  日期：1983.2

  series of nitroaromatic compounds, containing Cl, Br, or tosyl groups at various positions, were synthesized and studied by pulse radiolysis in aqueous alcohol solutions. One-electron reduction of the compounds produces the anion radicals which then undergo an intramolecular electron transfer and eliminate X/sup -/ (Cl/sup -/, Br/sup -/, or TsO/sup -/). The rates of X/sup -/ elimination vary over six orders

  合成了一系列在不同位置含有 Cl、Br 或甲苯磺酰基的硝基芳族化合物，并通过在乙醇水溶液中的脉冲辐解进行了研究。化合物的单电子还原产生阴离子自由基，然后进行分子内电子转移并消除 X/sup -/（Cl/sup -/、Br/sup -/ 或 TsO/sup -/）。X/sup -/ 消除率在六个数量级范围内变化，并受 CX 键解离能、连接 X 与 ..pi.. 系统的基团的大小和性质以及这些的相对位置的影响组。还证明了通过空间的分子内电子转移。
• Water-soluble quaternary ammonium heterocyclic azo dyestuffs
  申请人：Sterling Drug Inc.

  公开号：US03935182A1

  公开（公告）日：1976-01-27

  Water-soluble cationic dyestuffs of the formulae ##SPC1## Wherein R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NRO Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##EQU1## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge. k is a small integer whose value is dependent on the nature or A such that it has a range from one to two; R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ; R.sup.10 is lower-alkyl or lower-alkenyl; A.sup.1 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; g is a small integer whose value is dependent on the nature of A.sup.1 such that it has a range from one to two; R.sup.8.sup.' is lower-alkyl; R.sup.9.sup.' is lower-alkyl, lower alkenyl or hydroxy-lower-alkyl; R.sup.10.sup.' is lower-alkyl, lower -alkenyl or hydroxy-lower-alkyl or R.sup.9.sup.' and R.sup.10.sup.' together with the nitrogen atom are morpholino; A.sup.2 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; h is a small integer whose value is dependent on the nature of A.sup.2 such that it has a range from one to two; and An is an anion Are particularly useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials.

  具有以下公式的水溶性阳离子染料：##SPC1## 其中R.sup.0是氢，低烷基或羟基低烷基；R.sup.1是低烷基，低烯基或羟基低烷基；R.sup.2是低烷基，低烯基，羟基低烷基或-(低烷基)-NRO Y或R.sup.1和R.sup.2与氮原子一起，为吡咯烷基，哌嗪基或4-低烷酰基哌嗪基；Y是氢或##EQU1## 其中R是氢，低烷基，低烯基，苯基或苯基-低烷基；A是选自由芳香偶氮染料残基的一种，通过低烷基桥连接到季铵氮原子。k是小整数，其值取决于A的性质，范围从一到二；R.sup.8是低烷基，低烯基或羟基低烷基；R.sup.9是低烷基，羟基低烷基或NH.sub.2；R.sup.10是低烷基或低烯基；A.sup.1是通过低烷基桥连接到季铵氮原子上的芳香偶氮染料残基；g是小整数，其值取决于A.sup.1的性质，范围从一到二；R.sup.8.sup.'是低烷基；R.sup.9.sup.'是低烷基，低烯基或羟基低烷基；R.sup.10.sup.'是低烷基，低烯基或羟基低烷基或R.sup.9.sup.'和R.sup.10.sup.'与氮原子一起是吗啡基；A.sup.2是通过低烷基桥连接到季铵氮原子上的芳香偶氮染料残基；h是小整数，其值取决于A.sup.2的性质，范围从一到二；An是阴离子。这些染料特别适用于着色天然纤维，合成纤维成型材料和纤维素材料。