trimethyl-acetic acid 2-nitro-benzyl ester | 95735-85-6

• 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: trimethyl-acetic acid 2-nitro-benzyl ester
• 英文别名: (2-Nitrophenyl)methyl 2,2-dimethylpropanoate
• CAS: 95735-85-6
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: JEYUFAGFTKNSTP-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±17.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  trimethyl-acetic acid 2-nitro-benzyl ester 以 乙腈 为溶剂， 反应 1.17h， 生成 2-nitrosobenzaldehyde 、 三甲基乙酸
  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：

  2-硝基苄氯 、 三甲基乙酸 在 三乙胺 、 sodium iodide 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以82%的产率得到trimethyl-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

• Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane
  作者：Paolo Strazzolini、Antonio Runcio

  DOI：10.1002/ejoc.200390090

  日期：2003.2

  Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as − in the case

  二氯甲烷中的硝酸可成功用于将苄醇和醚氧化成相应的羰基化合物。所提出的方法被证明具有普遍适用性，醛和酮的收率非常好，并且在许多情况下显示出有趣的化学选择性，可以避免竞争性芳香硝化，以及 - 在醛的情况下 - 任何进一步氧化成羧酸. 该反应可能通过自由基机制进行，氧化过程中的活性物质是 NO2。在某些情况下观察到硝基酯的竞争性形成，而使用烯丙基和非苄基底物获得的结果不佳。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• 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。
• Process for preparing a carbapenem antibiotic
  申请人：JOHNSON MATTHEY PUBLIC LIMITED COMPANY

  公开号：US10011603B2

  公开（公告）日：2018-07-03

  A process for the preparation of a carbapenem, includes the step of treating a solution of a protected carbapenem with hydrogen gas in the presence of a heterogeneous catalyst to form the carbapenem, wherein the heterogeneous catalyst includes at least two platinum group metals.

  一种制备碳青霉烯类的工艺，包括在异相催化剂存在下用氢气处理受保护的碳青霉烯类溶液以形成碳青霉烯类的步骤，其中异相催化剂包括至少两种铂族金属。
• Light-sensitive composition
  申请人：——

  公开号：US20030190548A1

  公开（公告）日：2003-10-09

  There are disclosed a light-sensitive composition which comprises (A) at least one water-soluble polymer selected from a cationic water-soluble polymer having a phenyl group substituted by a vinyl group at a side chain of the polymer and a water-soluble polymer having a phenyl group substituted by a vinyl group and a sulfonate group at a side chain of the polymer, and (B) at least one of a photopolymerization initiator and a photo-acid generator; and a light-sensitive composition which comprises at least one cationic monomer having two or more polymerizable unsaturated groups in the molecule, at least one polymer, and at least one of a photopolymerizable initiator and a photo-acid generator.

  本发明公开了一种光敏组合物，它包括(A)至少一种水溶性聚合物，该聚合物选自在聚合物侧链上具有被乙烯基取代的苯基的阳离子水溶性聚合物和在聚合物侧链上具有被乙烯基取代的苯基和磺酸基的水溶性聚合物，以及(B)光聚合引发剂和光酸发生器中的至少一种；和一种光敏组合物，它包括至少一种阳离子单体，其分子中含有两个或两个以上可聚合的不饱和基团，至少一种聚合物，以及至少一种光聚合引发剂和一种光酸发生器。
• PHOTOLABILE ESTERS AND THEIR USES
  申请人：The Institute of Cancer Research

  公开号：EP1399412A1

  公开（公告）日：2004-03-24