1-(2-氯乙基)-2-硝基苯 | 28917-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-氯乙基)-2-硝基苯
• 英文名称: 2-(2-nitrophenyl)ethyl chloride
• 英文别名: 1-(2-chloroethyl)-2-nitrobenzene；2-nitro-phenethyl chloride；2-Nitro-phenaethylchlorid
• CAS: 28917-41-1
• 化学式: C₈H₈ClNO₂
• 分子量: 185.61
• InChiKey: TWVULDZVRRLVSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 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：

  1-(2-氯乙基)-2-硝基苯 在 硫酸 作用下， 生成 4-(2-硝基-苯基)-丁酸
  参考文献：
  名称：

  Joensson,N.A. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 317 - 321

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯乙苯 在 硫酸 、 硝酸 作用下， 生成 1-(2-氯乙基)-2-硝基苯
  参考文献：
  名称：

  Kurssanow; Kitschkina, Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1342,1344

  摘要：

  DOI：

文献信息

• Reduction of 1-(2-Chloroethyl)-2-nitrobenzene and 1-(2-Bromoethyl)-2-nitrobenzene at Carbon Cathodes: Electrosynthetic Routes to 1-Nitro-2-vinylbenzene and 1H-Indole
  作者：Peng Du、Dennis G. Peters

  DOI：10.1149/1.3482019

  日期：——

  nitro radical-anion immediately reacts as a base with the adjacent alkyl halide moiety via an E2 elimination to produce 1-nitro-2-vinylbenzene. At a potential corresponding to the first cathodic peak, bulk electrolyses of 1 or 2 in the absence of a proton donor afford 1-nitro-2-vinylbenzene as principal product, along with 1H-indole and a dimeric species. However, when 1 or 2 is electrolyzed in the

  研究 1-(2-氯乙基)-2-硝基苯 (1) 和 1-(2-溴乙基)-2-硝基苯 (2) 在含四甲基四氟硼酸铵 (TMABF 4 ) 的二甲基甲酰胺 (DMF) 中碳阴极的电化学还原已进行。1 和 2 的循环伏安图显示三个不可逆阴极峰，第一个归因于硝基的单电子还原，所得硝基阴离子立即作为碱与相邻的烷基卤部分反应，通过 E2 消除生产1-硝基-2-乙烯基苯。在对应于第一个阴极峰的电位下，在没有质子供体的情况下，1 或 2 的本体电解得到 1-硝基-2-乙烯基苯作为主要产物，以及 1H-吲哚和二聚体。然而，当 1 或 2 在苯酚或 2 存在下电解时，4-戊二酮作为质子源，唯一重要的产物是 1H-吲哚。提出了还原 1 和 2 的机理图，并且对 1-硝基-2-乙烯基苯的电化学行为进行了单独检查，作为这项工作的一部分。
• 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。
• [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。
• 7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-<i>e</i>]-1,2,4-triazolo[1,5-<i>c</i>]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility
  作者：Pier Giovanni Baraldi、Barbara Cacciari、Romeo Romagnoli、Giampiero Spalluto、Angela Monopoli、Ennio Ongini、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm010924c

  日期：2002.1.1

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.
• New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications
  作者：H. Giegrich、S. Eisele-Bühler、Chr Hermann、E. Kvasyuk、R. Charubala、W. Pfleiderer

  DOI：10.1080/07328319808004738

  日期：1998.9

  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.