2-(2-chloro-6-nitrophenyl)ethylsulfonyl chloride | 199122-94-6

• 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: 2-(2-chloro-6-nitrophenyl)ethylsulfonyl chloride
• 英文别名: 2-(2-Chloro-6-nitrophenyl)ethane-1-sulfonyl chloride；2-(2-chloro-6-nitrophenyl)ethanesulfonyl chloride
• CAS: 199122-94-6
• 化学式: C₈H₇Cl₂NO₄S
• 分子量: 284.12
• InChiKey: WEUFYFKDRYMYKH-UHFFFAOYSA-N

物化性质

• 沸点：
  387.5±32.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-6-nitrophenyl)ethylsulfonyl chloride 、 beta-胸苷 生成 [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(2-chloro-6-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-(2-氯-6-硝基苯基)乙醇 在 氯化亚砜 、 氯 、 sodium thiosulfate 作用下， 生成 2-(2-chloro-6-nitrophenyl)ethylsulfonyl chloride
  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

• [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。
• 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.
• NUCLEOSID-DERIVATE MIT PHOTOLABILEN SCHUTZGRUPPEN
  申请人：Pfleiderer, Wolfgang

  公开号：EP0901501A1

  公开（公告）日：1999-03-17
• US6153744A
  申请人：——

  公开号：US6153744A

  公开（公告）日：2000-11-28
• New Photolabile Protecting Groups of the 2-(2-Nitrophenyl)ethoxycarbonyl- and the 2-(2-Nitrophenyl)ethylsulfonyl-Type for the Oligonucleotide Synthesis
  作者：S. Bühler、H. Giegrich、W. Pfleiderer

  DOI：10.1080/07328319908044692

  日期：1999.6