(5-chloro-2-nitro-phenyl)-phenyl-methanol | 60794-27-6

• 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: (5-chloro-2-nitro-phenyl)-phenyl-methanol
• 英文别名: (5-chloro-2-nitrophenyl)(phenyl)methanol；5-Chlor-2-nitrobenzhydrol；(5-Chloro-2-nitrophenyl)-phenylmethanol
• CAS: 60794-27-6
• 化学式: C₁₃H₁₀ClNO₃
• 分子量: 263.68
• InChiKey: SATTULRDZPFHKU-UHFFFAOYSA-N

物化性质

• 沸点：
  439.6±40.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-chloro-2-nitro-phenyl)-phenyl-methanol 在 吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 trichloroacetic acid (5-dimethylamino-2-nitro-phenyl)-phenyl-methyl 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
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 、 phenylmagnesium bromide 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.33h， 以94%的产率得到(5-chloro-2-nitro-phenyl)-phenyl-methanol
  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

• From <i>in vitro</i> to <i>in cellulo</i>: structure–activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in <i>Pseudomonas aeruginosa</i>
  作者：Michael P. Storz、Giuseppe Allegretta、Benjamin Kirsch、Martin Empting、Rolf W. Hartmann

  DOI：10.1039/c4ob00707g

  日期：——

  More than 60 derivatives of (2-nitrophenyl)methanol were synthesized and evaluated regarding their potency to inhibit PqsD. In vitro and in cellulo structure–activity relationships were derived.

  超过60种(2-硝基苯基)甲醇衍生物被合成并评估其抑制PqsD的效力。得出了体外和体内结构-活性关系。
• Substituted 2-nitrobenzyltrichloroacetate esters for photodirected oligonucleotide detritylation in solid films
  作者：Pawel J. Serafinowski、Peter B. Garland

  DOI：10.1039/b806902f

  日期：——

  Oligonucleotide microarray fabrication by chemical synthesis using photoacid generators in solid films could have advantages over existing methods, but has not matched the accuracy of conventional synthesis where detritylation is performed with acid solutions. To address this problem, we explored the kinetics and equilibria of nucleoside detritylation in solid films, using trichloroacetic acid (TCA)

  通过使用固态膜中的光致产酸剂进行化学合成的寡核苷酸微阵列制造可能具有优于现有方法的优势，但与以酸溶液进行去三苯甲基化的常规合成方法的准确性不匹配。为了解决这个问题，我们使用由三氯乙酸（TCA）从其酯与取代的2-硝基苄基醇进行光解生成的三氯乙酸（TCA），探索了固体膜中核苷去三苯甲基化的动力学和平衡。我们合成了25种被所有α-苯基取代的酯，并评估了它们作为固体膜光致产酸剂的潜力。它们包括在（2-i-硝基）中具有（i）单或二甲氧基或（ii）5-卤代，（iii）烷基或芳基取代的5-氨基或（iv）5-芳基取代基的组。或2，6-二硝基苄基环。其紫外线光谱的最大吸收范围为230至410 nm，在365 nm处的量子产率从<0.01到接近1.0。所述酯在载玻片上形成光学透明的固体膜，而没有添加聚合物。膜内光酸生成，质子活性变化和去三苯甲基化的动力学进行了现场测量。对光敏感性和去三苯甲基化最有效的酯是5-氯-，5-溴-，4
• 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。
• Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/ Propargylation−Cyclization
  作者：Jinmin Fan、Changfeng Wan、Gaojun Sun、Zhiyong Wang

  DOI：10.1021/jo8017654

  日期：2008.11.7

  Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.
• WALSER A.; ZENCHOFF G., J. HETEROCYCL. CHEM. <JHTC-AD>, 1976, 13, NO 4, 907-908
  作者：WALSER A.、 ZENCHOFF G.

  DOI：——

  日期：——