trichloro-acetic acid 2-nitro-benzyl ester

• 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: trichloro-acetic acid 2-nitro-benzyl ester
• 英文别名: 2-Nitrobenzyl-trichloroacetate；(2-nitrophenyl)methyl 2,2,2-trichloroacetate
• 化学式: C₉H₆Cl₃NO₄
• 分子量: 298.51
• InChiKey: IJBCYQZVWXAIIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trichloro-acetic acid 2-nitro-benzyl ester 以 乙腈 为溶剂， 反应 1.17h， 生成 2-nitrosobenzaldehyde 、 三氯乙酸
  参考文献：
  名称：

  Novel Photoacid Generators for Photodirected Oligonucleotide Synthesis

  摘要：

  Photodirected oligonucleotide synthesis uses either direct or indirect light-dependent 5'deprotection. Both have been reported to give lower stepwise synthetic yields than conventional methods. The deficiency appears to be due to incomplete deprotection at the, oligonucleotide 5'-position and, additionally in the case where photodirection is indirect and uses photogenerated photoacid to effect 5'-detritylation, the depurinating effects of strong acid. We have developed novel photosensitive-2-nitrobenzyl esters that on irradiation with near UV light generate alpha-chloro-substituted acetic acids, such as trichloroacetic acid, which are widely and successfully used in conventional solid-phase oligonucleotide synthesis. alpha-Phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate and alpha-phenyl-4,5-dimethoxy-2,6-dinitrobenzyltrichloroacetate showed appropriate photochemical characteristics and were used for photodirected synthesis of a variety of oligonucleotides, including (T)(5), TATAT, TGTGT, (T)(10), (AT)(5), (CT)(5) (GT)(5), and (TGCAT)(2) on a modified Millipore Expedite DNA synthesizer. The outcomes were compared with those obtained by use of directly added trichloroacetic acid (conventional synthesis). The stepwise yields for the two methods were essentially identical.

  DOI：

  10.1021/ja017635y
• 作为产物：
  描述：

  邻硝基苯甲醇 、 三氯乙酸 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以70%的产率得到trichloro-acetic acid 2-nitro-benzyl ester
  参考文献：
  名称：

  Novel Photoacid Generators for Photodirected Oligonucleotide Synthesis

  摘要：

  Photodirected oligonucleotide synthesis uses either direct or indirect light-dependent 5'deprotection. Both have been reported to give lower stepwise synthetic yields than conventional methods. The deficiency appears to be due to incomplete deprotection at the, oligonucleotide 5'-position and, additionally in the case where photodirection is indirect and uses photogenerated photoacid to effect 5'-detritylation, the depurinating effects of strong acid. We have developed novel photosensitive-2-nitrobenzyl esters that on irradiation with near UV light generate alpha-chloro-substituted acetic acids, such as trichloroacetic acid, which are widely and successfully used in conventional solid-phase oligonucleotide synthesis. alpha-Phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate and alpha-phenyl-4,5-dimethoxy-2,6-dinitrobenzyltrichloroacetate showed appropriate photochemical characteristics and were used for photodirected synthesis of a variety of oligonucleotides, including (T)(5), TATAT, TGTGT, (T)(10), (AT)(5), (CT)(5) (GT)(5), and (TGCAT)(2) on a modified Millipore Expedite DNA synthesizer. The outcomes were compared with those obtained by use of directly added trichloroacetic acid (conventional synthesis). The stepwise yields for the two methods were essentially identical.

  DOI：

  10.1021/ja017635y

文献信息

• METHODS OF SYNTHESIZING A POLYNUCLEOTIDE ARRAY USING PHOTOACTIVATED AGENTS
  申请人：Vibrant Holdings, LLC

  公开号：US20210380629A1

  公开（公告）日：2021-12-09

  Described herein are methods for the synthesis of DNA polynucleotides and polynucleotides, as well as methods for their deprotection and methods for the use of said compounds and compositions comprising said compounds. In particular, such compounds and compositions comprising them are used in methods for light-directed synthesis of DNA microarrays.

  本文描述了合成DNA多核苷酸和多核苷酸的方法，以及它们的去保护方法、使用这些化合物的方法和包含这些化合物的组合物的方法。特别是，这些化合物和包含它们的组合物用于DNA微阵列的光导向合成方法。
• Photolabile esters and their uses
  申请人：——

  公开号：US20040242653A1

  公开（公告）日：2004-12-02

  Compounds which are capable of generating acid on photolysis are disclosed, and the uses of these compounds, especially for deprotecting the termini of nucleic acid molecules or peptides during synthesis of arrays. The compounds described herein may be employed in the detritylation of 5′-O-dimethoxytrityl (DMT) protected nucleotides by photolysing the compounds to generate an acid capable of removing the DMT group allowing oligonucleotide arrays to be synthesised using readily available 5′-O-DMT-nucleoside-3′-O-phosphoramidite monomers conventionally used in solid phase nucleic acid synthesis. A method of avoiding the effects of stray light in projection lithography techniques is also disclosed.

  本文披露了能够在光解作用下产生酸的化合物，并介绍了这些化合物的用途，特别是在合成阵列期间去保护核酸分子或肽的末端。本文所描述的化合物可用于通过光解产生能够去除DMT基团的酸来去除5'-O-二甲氧基三苯基甲酰（DMT）保护的核苷酸，从而使用常规固相核酸合成中使用的易得的5'-O-DMT-核苷酸-3'-O-磷酸酰胺单体合成寡核苷酸阵列。本文还披露了一种避免投影光刻技术中杂散光影响的方法。
• Resist material and process for forming pattern using the same
  申请人：WAKO PURE CHEMICAL INDUSTRIES LTD

  公开号：EP0476865A1

  公开（公告）日：1992-03-25

  A resist material of chemical amplified type comprising (a) a polymer such as a polymer of 1-methylcycloalkyl 4-ethenylphenoxyacetate and 4-hydroxystyrene, etc., (b) a photo-sensitive compound capable of generating an acid when exposed to light, and (c) a solvent for dissolving both the components (a) and (b) is excellent in heat resistance and adhesiveness to substrates, capable of maintaining stable pattern dimension from exposure to light to heat treatment, and capable of forming patterns using deep ultraviolet light, KrF excimer laser light, etc.

  一种化学放大型抗蚀剂材料，包括（a）聚合物，如 1-甲基环烷基 4-乙烯基苯氧乙酸酯和 4-羟基苯乙烯等的聚合物、(c) 用于溶解(a)和(b)两种成分的溶剂。这种抗蚀剂具有优异的耐热性和与基材的粘合性，从受光到热处理都能保持稳定的图案尺寸，并能使用深紫外线、KrF 准分子激光等形成图案。
• PHOTOSENSITIVE POLYSILAZANE COMPOSITION AND METHOD OF FORMING PATTERNED POLYSILAZANE FILM
  申请人：TonenGeneral Sekiyu K.K.

  公开号：EP1164435A1

  公开（公告）日：2001-12-19

  A photosensitive polysilazane which may be used as a positive-tone photoresist, and a method of forming a patterned polysilazane film by use of such a composition are provided. The photosensitive polysilazane composition of the invention is characterized by comprising a polysilazane, particularly polymethylsilazane or polyphenylsilazane, and an optically acid-generating agent. The patterned polysilazane film is obtained by exposing a coating of the photosensitive polysilazane composition of the invention to light in a pattern and dissolving off the exposed portion.

  本发明提供了一种可用作正色调光刻胶的光敏聚硅氮烷，以及使用这种组合物形成图案化聚硅氮烷薄膜的方法。本发明的光敏聚硅氮烷组合物的特点是由一种聚硅氮烷（特别是聚甲基硅氮烷或聚苯基硅氮烷）和一种光学酸生成剂组成。将本发明的光敏聚硅氮烷组合物涂层按一定图案对光照射，然后溶解掉照射部分，即可得到图案化的聚硅氮烷薄膜。
• PHOTOSENSITIVE POLYSILAZANE COMPOSITION, METHOD OF FORMING PATTERN THEREFROM, AND METHOD OF BURNING COATING FILM THEREOF
  申请人：CLARIANT INTERNATIONAL LTD.

  公开号：EP1239332A1

  公开（公告）日：2002-09-11

  A finely patterned silica type ceramic film suitable as an inter-layer dielectric is formed in a short time by applying, onto a substrate, a positive working radiation sensitive polysilazane composition comprising a modified poly(sil sesquiazane) having a number average molecular weight of 100 to 100,000 and containing a basic constituent unit represented by the general formula: -[SiR6(NR7)1.5]- and other constituent units represented by the general formula: -[SiR62NR7]- and/or -[SiR63(NR7)0.5]- (R6 and R7 independently represent a hydrogen atom, a C1-3 alkyl group or a substituted or unsubstituted phenyl group) in a ratio of 0.1 to 100 mol-% to said basic constituent unit, a photo acid generator and preferably a water-soluble compound as a shape stabilizer, then patternwise exposing the resultant coating film, subjecting the exposed part of the coating film to moistening treatment, developing it with an aqueous alkali solution, wholly exposing the coating film to light and moistening treatment again, followed by burning treatment.

  一种适用于层间电介质的精细图案化二氧化硅型陶瓷膜是通过在基底上涂敷一种正工作辐射敏感性聚硅氮烷组合物在短时间内形成的，该组合物包含一种改性聚硅氮烷，其平均分子量为 100 至 100000，并含有由通式表示的基本组成单元：-[SiR6(NR7)1.5]-和由通式代表的其他组成单元：-[SiR62NR7]-和/或-[SiR63(NR7)0.5]-(R6 和 R7 独立地代表氢原子、C1-3 烷基或取代或未取代的苯基)，与所述基本组成单元的比例为 0.然后，将所得涂膜进行图案化曝光，将涂膜的曝光部分进行湿润处理，用碱水溶液显影，将涂膜完全曝光于光并再次进行湿润处理，然后进行灼烧处理。