2-(5-Benzoyl-2-nitrophenyl)-1-propanol | 748789-28-8

• 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-(5-Benzoyl-2-nitrophenyl)-1-propanol
• 英文别名: [3-(1-hydroxypropan-2-yl)-4-nitrophenyl]-phenylmethanone
• CAS: 748789-28-8
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: PRBFMISPUYEBSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸三氯甲酯 、 2-(5-Benzoyl-2-nitrophenyl)-1-propanol 、 三乙胺 在 四氢呋喃 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以to give 19f as yellow oil的产率得到2-(5-Benzoyl-2-nitrophenyl)-1-propyl oxycarbonylchloride
  参考文献：
  名称：

  NOVEL PHOTOLABILE PROTECTIVE GROUPS FOR IMPROVED PROCESSES TO PREPARE OLIGONUCLEOTIDE ARRAYS

  摘要：

  本发明揭示了新型和改进的核苷酸和核苷酸化合物，其在寡核苷酸的光导向合成中有用，以及其制备的方法和试剂。这些化合物的特点是具有新型光敏保护基，该保护基连接到核苷酸基团的5'-或3'-羟基。光敏保护基由2-(2-硝基苯基)-乙氧羰基骨架组成，其芳环上至少有一个取代基，可以是芳基、芳酰基、杂环芳基或烷氧羰基基团。本发明包括上述化合物在光导向寡核苷酸合成中的使用，核酸微阵列的相应组装及其应用。

  公开号：

  US20100292458A1
• 作为产物：
  描述：

  硝基乙苯 在 2-甲基苯磺酸 盐酸 、 氢氧化钾 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 生成 2-(5-Benzoyl-2-nitrophenyl)-1-propanol
  参考文献：
  名称：

  RECENT HIGHLIGHTS ON PHOTOLITHIC OLIGONUCLEOTIDE ARRAY IN SITU SYNTHESIS

  摘要：

  Light directed synthesis of high-densily oligonucleotide microarrays is currently performed using either ortho-nitro benzyl-type [MeNPOC/ (Pease, A.C; Solas, D.; Sullivan, E.J.; Cronin, TM.; Holmes, CP; Fodor, S.P.A. Proc. Natl. Acad. Sci U.S.A. 1994, 91, 6333.) or ortho-nitrophenylethyl-type [NPPOC] (Hasan, A.; Stengele, K.P.; Giegrich, H; Cornwell, P.; Isham, K.R.; Sachleben, R.A.; Pfleiderer, W.; Foote, R.S. Tetrahedron 1997, 53, 4247) protecting groups as the 5'-O-carbonate ester of the phosphoramidite building block. The synthesis cycle uses a combinatorial approach attaching one specific base per cycle, thus as many as 100 cycles need to be run to make an array of 25-mers. Time needed for deprotection/activation of the growing oligo chain determines overall manufacturing time and consequently also cost. In this report we demonstrate the development of photoprotected phosphoramidite monomers for light directed array synthesis with increasing sensitivity to the UV light used. If combined with maskless array synthesis, this technology allows for synthesis of arrays with >780,000 different 25-mer oligonucteolides in about one hour and allows for high flexibility in array design and reiterative redesign. The arrays synthesized show high quality and reproducibility in our standard hybridization based assay.

  DOI：

  10.1081/ncn-200059241

文献信息

• Novel photolabile protective groups for improved processes to prepare oligonucleotide arrays
  申请人：NIGU Chemie GmbH

  公开号：US20040175741A1

  公开（公告）日：2004-09-09

  The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5′- or the 3′-hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl)-ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.

  本发明揭示了新型和改良的核苷酸和核苷酸化合物，可用于寡核苷酸的光导向合成，以及它们的制备方法和试剂。这些化合物的特点是具有新型光敏保护基，该保护基连接到核苷酸基团的5'-或3'-羟基上。光敏保护基由2-(2-硝基苯基)-乙氧羰基骨架组成，芳环上至少有一个取代基，可以是芳基、芳酰基、杂环芳基或烷氧羰基基团。本发明包括上述化合物在光导向寡核苷酸合成、核酸微阵列的组装及其应用中的使用。
• NOVEL PHOTOLABILE PROTECTIVE GROUPS FOR IMPROVED PROCESSES TO PREPARE OLIGONUCLEOTIDE ARRAYS
  申请人：BÜHLER Sigrid

  公开号：US20100292458A1

  公开（公告）日：2010-11-18

  The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5′- or the 3′-hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl)-ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.

  本发明揭示了新型和改进的核苷酸和核苷酸化合物，其在寡核苷酸的光导向合成中有用，以及其制备的方法和试剂。这些化合物的特点是具有新型光敏保护基，该保护基连接到核苷酸基团的5'-或3'-羟基。光敏保护基由2-(2-硝基苯基)-乙氧羰基骨架组成，其芳环上至少有一个取代基，可以是芳基、芳酰基、杂环芳基或烷氧羰基基团。本发明包括上述化合物在光导向寡核苷酸合成中的使用，核酸微阵列的相应组装及其应用。
• US7759513B2
  申请人：——

  公开号：US7759513B2

  公开（公告）日：2010-07-20
• US8445734B2
  申请人：——

  公开号：US8445734B2

  公开（公告）日：2013-05-21
• [EN] NOVEL PHOTOLABILE PROTECTIVE GROUPS FOR IMPROVED PROCESSES TO PREPARE OLIGONUCLEOTIDE ARRAYS<br/>[FR] NOUVEAUX GROUPES DE PROTECTION PHOTOLABILES POUR DES PROCEDES AMELIORES DE PREPARATION DE RESEAUX OLIGONUCLEOTIDIQUES
  申请人：NIGU CHEMIE GMBH

  公开号：WO2004074300A2

  公开（公告）日：2004-09-02

  The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5'- or the 3'- hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl) ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.