4-chloro-1-(2-chloroethyl)-2-nitro-benzene | 52536-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-1-(2-chloroethyl)-2-nitro-benzene
• 英文别名: 2-(4-chloro-2-nitrophenyl)ethyl chloride；4-chloro-1-(2-chloroethyl)-2-nitrobenzene
• CAS: 52536-97-7
• 化学式: C₈H₇Cl₂NO₂
• 分子量: 220.055
• InChiKey: SSPQKEFEPHFKAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  300.9±27.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-1-(2-chloroethyl)-2-nitro-benzene 在 氯 、 sodium thiosulfate 作用下， 生成 [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(4-chloro-2-nitrophenyl)ethanesulfonate
  参考文献：
  名称：

  New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications

  摘要：

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.

  DOI：

  10.1080/07328319808004738
• 作为产物：
  描述：

  2-(4-氯-2-硝基-苯基)-乙醇 在 氯化亚砜 作用下， 生成 4-chloro-1-(2-chloroethyl)-2-nitro-benzene
  参考文献：
  名称：

  New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications

  摘要：

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.

  DOI：

  10.1080/07328319808004738

文献信息

• Nucleoside derivatives with photolabile protective groups
  申请人：Wolfgang Pfleiderer

  公开号：US06153744A1

  公开（公告）日：2000-11-28

  The invention relates to nucleo-side derivatives with photo-unstable protective groups of the general formula (I) ##STR1## in which R.sup.1 is H, NO.sub.2, CN, OCH.sub.3, halogen, alkyl or alkoxyalkyl with 1 to 4 C atoms, R.sup.2 is H, OCH.sub.3, R.sup.3 is H, F, Cl, Br, NO.sub.2 or an aliphatic acyl radical with 2 to 5 C atoms, R.sup.4 is H, halogen, OCH.sub.3, an alkyl radical with 1 to 4 C atoms or a possibly substituted aryl radical, R.sup.5 is H or a conventional functional group for producing oligonucleotides, R.sup.6 is H, OH, halogen or XR.sup.8, where X is O or S and R.sup.8 is a conventional protective group in nucleotide chemistry, B is adenine, cytosin, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazol carboxylic acid amid-1-yl or 5-amino-4-imidazol carboxylic acid amide-3-yl, where, if B is adenine, cytosin or guanine, the primary amino function may have a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.

  该发明涉及具有一般式（I）的光不稳定保护基的核苷衍生物，其中R.sup.1为H、NO.sub.2、CN、OCH.sub.3、卤素、1至4个碳原子的烷基或烷氧基烷基，R.sup.2为H、OCH.sub.3，R.sup.3为H、F、Cl、Br、NO.sub.2或具有2至5个碳原子的脂肪酸酰基基团，R.sup.4为H、卤素、OCH.sub.3、具有1至4个碳原子的烷基基团或可能取代的芳基基团，R.sup.5为H或用于产生寡核苷酸的常规功能基团，R.sup.6为H、OH、卤素或XR.sup.8，其中X为O或S，R.sup.8为核苷酸化学中的常规保护基团，B为腺嘌呤、胞嘧啶、鸟嘌呤、胸腺嘧啶、尿嘧啶、2,6-二氨基嘌呤-9-基、次黄嘌呤-9-基、5-甲基胞嘧啶-1-基、5-氨基-4-咪唑甲酸酰胺-1-基或5-氨基-4-咪唑甲酸酰胺-3-基，如果B为腺嘌呤、胞嘧啶或鸟嘌呤，则初级氨基功能可能具有永久保护基。这些衍生物可用于在DNA芯片上进行光控合成寡核苷酸。
• [EN] MACROCYCLIC QUINAZOLINE DERIVATIVES AS ANTIPROLIFERATIVE AGENTS<br/>[FR] DERIVES DE QUINAZOLINE MACROCYCLIQUE UTILISES COMME AGENTS ANTIPROLIFERATIFS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004105765A1

  公开（公告）日：2004-12-09

  The present invention concerns the compounds of formula (I) the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Z represents O, CH2, NH or S; in particular Z represents NH; Y represents -C3-9alkyl-, -C3-9alkenyl-, -C3-9alkynyl-, -C3-7alkyl-CO-NH- optionally substituted with amino, mono- or di(C1-4alkyl)amino or C1-4 alkyloxycarbonylamino-, -C3-7alkenyl-CO-NH- optionally substituted with amino, mono- or di(C1-4alkyl)amino- or C1-4alkyloxycarbonylamino-, C1-5alkyl-oxy-C1-5alkyl-, -C1-5alkyl NR13-, -C1-5alkyl-, -C1-5alkyl-NR14-CO-C1-5alkyl-, -C1-5alkyl-CO NR15-C1-5alkyl-, -C1-6alkyl-CO-NH-, -C1-6alkyl-NH-CO-, -C1-3alkyl-NH-CS-Het20-, -C1-3alkyl-NH-CO-Het20-, -C1-2alkyl-CO-Het21-CO-, -Het22-CH2-CO-NH-C1-3alkyl-, -CO-NH-C1-6alkyl-, -NH-CO-C1-6alkyl-, -CO-C1-7alkyl-, -C1-7alkyl-CO-, -C1-6alkyl-CO-C1-6alkyl-, -C1-2alkyl-NH-CO-CR16R17-NH-, -C1-2alkyl-CO-NH-CR18R19-CO-, -C1-2alkyl-CO-NR20-C1-3alkyl-CO-, C1-2alkyl-NR21-CH2-CO-NH-C1-3alkyl-, or -NR22-CO-C1-3alkyl-NH-; X1 represents a direct bond, O or -O-C1-2alkyl-, CO, -CO-C1-2alkyl-, NR11, -NR11-C1-2alkyl-, CH2-, -O-N=CH- or -C1-2alkyl-; X2 represents a direct bond, O, -O-C1-2alkyl-, CO, -CO-C1-2alkyl-, NR12, -NR12-C1-2alkyl-, -CH2-, -O-N=CH- or -C1-2alkyl-. The growth inhibitory effect anti-tumour activity of the present compounds has been demonstrated in vitro, in enzymatic assays on the receptor tyrosine kinase EGFR.

  本发明涉及公式（I）的化合物，其N-氧化物形式，药用可接受的加合物盐及其立体化异构形式，其中Z代表O、CH2、NH或S；特别是Z代表NH；Y代表-C3-9烷基，-C3-9烯基，-C3-9炔基，-C3-7烷基-CO-NH-（可选择地被氨基，单或双（C1-4烷基）氨基或C1-4烷氧羰氨基取代），-C3-7烯基-CO-NH-（可选择地被氨基，单或双（C1-4烷基）氨基或C1-4烷氧羰氨基取代），C1-5烷氧基-C1-5烷基，-C1-5烷基-NR13-，-C1-5烷基，-C1-5烷基-NR14-CO-C1-5烷基，-C1-5烷基-CO NR15-C1-5烷基，-C1-6烷基-CO-NH-，-C1-6烷基-NH-CO-，-C1-3烷基-NH-CS-Het20-，-C1-3烷基-NH-CO-Het20-，-C1-2烷基-CO-Het21-CO-，-Het22-CH2-CO-NH-C1-3烷基-，-CO-NH-C1-6烷基-，-NH-CO-C1-6烷基-，-CO-C1-7烷基-，-C1-7烷基-CO-，-C1-6烷基-CO-C1-6烷基-，-C1-2烷基-NH-CO-CR16R17-NH-，-C1-2烷基-CO-NH-CR18R19-CO-，-C1-2烷基-CO-NR20-C1-3烷基-CO-，C1-2烷基-NR21-CH2-CO-NH-C1-3烷基-，或-NR22-CO-C1-3烷基-NH-；X1代表直接键，O或-O-C1-2烷基-，CO，-CO-C1-2烷基-，NR11，-NR11-C1-2烷基-，CH2-，-O-N=CH-或-C1-2烷基-；X2代表直接键，O，-O-C1-2烷基-，CO，-CO-C1-2烷基-，NR12，-NR12-C1-2烷基-，-CH2-，-O-N=CH-或-C1-2烷基-。本发明化合物的生长抑制效应和抗肿瘤活性已在体外实验中，在EGFR受体酪氨酸激酶的酶促活性测定中得到证明。
• Quinazoline derivatives
  申请人：Janssen Pharmaceutica NV

  公开号：EP2305687A1

  公开（公告）日：2011-04-06

  The present invention concerns the compounds of formula the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Z represents NH; Y represents -C3-9alkyl-, -C2-9alkenyl-, -C3-7alkyl-CO-NH optionally substituted with amino, mono - or di(C1-4alkyl)amino or C1-4alkyloxycarbonylamino-, -C3-7alkenyl-CO-NH- optionally substituted with amino, mono- or di(C1- 4alkyl)amino- or C1-4alkyloxycarbonylamino-, C1-5alkyl-NR13-C1-5alkyl-, -C1-5alkyl-NR14-CO-C1-5alkyl-, -C1-6alkyl-CO-NH-, -C1-5alkyl-CO NR15-C1-5alkyl-, -C1-3alkyl-NH-CO-Het20-, -C1-2alkyl-CO-Het21-CO-, -C1-2alkyl-NH-CO-CR16R17-NH-, -C1-2alkyl-CO-NH-CR18R19-CO-, -C1-2alkyl-CO-NR20-C1-3alkyl-CO-, or -NR22-CO-C1-3alkyl-NH-; X1 represents a direct bond, O or-O-C1-2alkyl-; X2 represents a direct bond, -CO-C1- 2alkyl-, NR12, -NR12-C1-2alkyl-, -O-N=CH- or -C1-2alkyl-; R1 and R2 each independently represents hydrogen or halo; R3 represents hydrogen; R4 represents hydrogen or C1-4alkyloxy; R12 and R13 each independently represents hydrogen or C1-4alkyl; R14 and R15 represents hydrogen; R16 and R17 each independently represent hydrogen or C1-4alkyl; R18 and R19 each independently represent hydrogen or C1-4alkyl optionally substituted with phenyl or hydroxy; R20 and R21 each independently represent hydrogen or C1-4alkyl optionally substituted with C1-4alkyloxy; Het20, Het21 and Het22 each independently represent a heterocycle selected from the group consisting pyrrolidinyl, 2-pyrrolidinonyl or piperidinyl optionally substituted with hydroxy.

  本发明涉及式化合物 的 N-氧化物形式、药学上可接受的加成盐及其立体异构形式，其中 Z 代表 NH Y 代表-C3-9烷基-、-C2-9烯基-、-C3-7烷基-CO-NH，任选被氨基、单-或二(C1-4烷基)氨基或 C1-4 烷氧基羰基氨基取代、 -C3-7烷基-CO-NH-任选被氨基、单-或二(C1-4烷基)氨基-或 C1-4烷氧基羰基氨基-取代、 C1-5alkyl-NR13-C1-5alkyl-, -C1-5alkyl-NR14-CO-C1-5alkyl-, -C1-6alkyl-CO-NH-, -C1-5烷基-CO NR15-C1-5烷基-，-C1-3烷基-NH-CO-Het20-、 -C1-2alkyl-CO-Het21-CO-, -C1-2alkyl-NH-CO-CR16R17-NH-, -C1-2alkyl-CO-NH-CR18R19-CO-, -C1-2alkyl-CO-NR20-C1-3alkyl-CO-, or -NR22-CO-C1-3alkyl-NH-; X1 代表直接键、O 或-O-C1-2烷基-； X2 代表直接键、-CO-C1-2烷基-、NR12、-NR12-C1-2烷基-、-O-N=CH- 或-C1-2烷基-； R1 和 R2 各自独立地代表氢或卤素； R3 代表氢； R4 代表氢或 C1-4 烷氧基； R12和R13各自独立地代表氢或C1-4烷基 R14 和 R15 各自独立地代表氢或 C1-4 烷基； R18 和 R19 各自独立地代表氢或任选被苯基或羟基取代的 C1-4 烷基； R20 和 R21 各自独立地代表氢或被 C1-4 烷氧基任选取代的 C1-4 烷基； Het20、Het21 和 Het22 各自独立地代表选自由羟基取代的吡咯烷基、2-吡咯烷壬基或哌啶基组成的杂环。
• [DE] NUCLEOSID-DERIVATE MIT PHOTOLABILEN SCHUTZGRUPPEN<br/>[EN] NUCLEOSIDE DERIVATIVES WITH PHOTO-UNSTABLE PROTECTIVE GROUPS<br/>[FR] DERIVES DE NUCLEOSIDES A GROUPES PROTECTEURS PHOTOLABILES
  申请人：PFLEIDERER, Wolfgang

  公开号：WO1997044345A1

  公开（公告）日：1997-11-27

  (DE) Die Erfindung betrifft Nucleosid-Derivate mit photolabilen Schutzgruppen der allgemeinen Formel (I), in der R1 = H, NO2, CN, OCH3, Halogen, Alkyl oder Alkoxyalkyl mit 1 bis 4 C-Atomen, R2 = H, OCH3, R3 = H, F, Cl, Br, NO2 oder ein aliphatischer Acylrest mit 2 bis 5 C-Atomen, R4 = H, Halogen, OCH3, ein Alkylrest mit 1 bis 4 C-Atomen oder ein ggf. substituierter Arylrest, R5 = H oder eine übliche funktionelle Gruppe zur Herstellung von Oligonucleotiden, R6 = H, OH, Halogen oder XR8, wobei X = O oder S und R8 eine in der Nucleotidchemie übliche Schutzgruppe darstellt, B = Adenin, Cytosin, Guanin, Thymin, Uracil, 2,6-Diaminopurin-9-yl, Hypoxanthin-9-yl, 5-Methylcytosin-1-yl, 5-Amino-4-imidazolcarbonsäureamid-1-yl oder 5-Amino-4-imidazolcarbonsäureamid-3-yl, wobei im Falle von B = Adenin, Cytosin oder Guanin die primäre Aminofunktion ggf. eine permanente Schutzgruppe aufweist. Diese Derivate können für die lichtgesteuerte Synthese von Oligonucleotiden auf einem DNA-Chip verwendet werden.(EN) The invention relates to nucleoside derivatives with photo-unstable protective groups of the general formula (I) in which R1 is H, NO2, CN, OCH3, halogen, alkyl or alkoxyalkyl with 1 to 4 C atoms, R2 is H, OCH3, R3 is H, F, Cl, Br, NO2 or an aliphatic acyl radical with 2 to 5 C atoms, R4 is H, halogen, OCH3, an alkyl radical with 1 to 4 C atoms or a possibly substituted aryl radical, R5 is H or a conventional functional group for producing oligonucleotides, R6 is H, OH, halogen or XR8, where X is O or S and R8 is a conventional protective group in nucleotide chemistry, B is adenine, cytosin, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazol carboxylic acid amid-1-yl or 5-amino-4-imidazol carboxylic acid amide-3-yl, where, if B is adenine, cytosin or guanine, the primary amino function may have a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.(FR) L'invention concerne des dérivés nucléosidiques à groupes protecteurs photolabiles de la formule générale (I) dans laquelle R1 est H, NO2, CN, OCH3, halogène, alkyle ou bien alcoxyalkyle avec 1 à 4 atomes de C, R2 est H, OCH3, R3 est H, F, Cl, Br, NO2 ou un radical acyle aliphatique avec 2 à 5 atomes de C, R4 est H, halogène, OCH3, un radical alkyle avec 1 à 4 atomes de C ou bien un radical aryle éventuellement substitué, R5 est H ou un groupe fonctionnel usuel pour la production d'oligonucléotides, R6 est H, OH, halogène ou bien XR8 où X est O ou S et R8 est un groupe protecteur usuel dans la chimie des nucléotides, B est adénine, cytosine, guanine, thymine, uracile, 2,6-diaminopurin-9-yle, hypoxanthin-9-yle, 5-méthylcytosin-1-yle, amid-1-yle d'acide 5-amino-4-imidazolcarboxylique ou bien amid-3-yle d'acide 5-amino-4-imidazolcarboxylique, et si B est adénine, cytosine ou guanine, la fonction amino primaire peut présenter un groupe protecteur permanent. Ces dérivés peuvent s'utiliser pour la synthèse photorégulée d'oligonucléotides sur une plaquette d'ADN.

  这项发明涉及一类具有光不稳定的保护基团的核苷酸衍生物，其一般化学式为(I)。其中， R1代表H、NO2、CN、OCH3、卤素、烷基或甲氧基丙基，其中每个结构中的碳原子数量分别为1到4个。R2代表H、OCH3。R3代表H、F、Cl、Br、NO2或含2至5个碳原子的直链羰基基团(R3)。R4代表H、卤素、OCH3、烷基(1至4个碳)或可能取代的苯基基团。R5代表H或用于生产寡链核苷酸的常规功能基团。R6代表H、OH、卤素或XR8，此处X为O或S，R8代表常用于核苷酸化学的普通保护基团。 在此的B代表腺嘌呤(A)、鸟嘌呤(C)、胞嘧啶(G)、胸腺嘧啶(T)、尿嘧啶(U)、2,6-二胺嘌呤-9-位(2,6-bis-azido-9-yl)、Hypoxanthin-9-yl、5-甲基胞嘧啶-1-yl、5-氨基-4-甲基嘧啶-4-COOH酰胺-1-yl或5-氨基-4-甲基嘧啶-4-COOH酰胺-3-yl，其中在B为腺嘌呤、鸟嘌呤或胞嘧啶的情况下，主要氨基可能带有永久性保护基团。这些衍生物可以用于光控寡链核苷酸在DNA微芯片上的合成。
• METHOD FOR PURIFYING PYRUVIC ACID COMPOUNDS
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0937703B1

  公开（公告）日：2003-05-21