(4,5-dimethoxy-2-nitro-phenyl)-(3-methoxy-phenyl)-methanol

• 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: (4,5-dimethoxy-2-nitro-phenyl)-(3-methoxy-phenyl)-methanol
• 英文别名: (4,5-dimethoxy-2-nitrophenyl)(3-methoxyphenyl)methanol；(4,5-Dimethoxy-2-nitrophenyl)-(3-methoxyphenyl)methanol
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: AQNVWPSGZFEYCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4,5-dimethoxy-2-nitro-phenyl)-(3-methoxy-phenyl)-methanol 、 三氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以81%的产率得到trichloroacetic acid (4,5-dimethoxy-2-nitro-phenyl)-(3-methoxy-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：

  (3-methoxyphenyl)magnesium bromide 、 6-硝基藜芦醛 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 以81%的产率得到(4,5-dimethoxy-2-nitro-phenyl)-(3-methoxy-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

• Quantifying factors that influence metal ion release in photocaged complexes using ZinCast derivatives
  作者：Celina Gwizdala、Charlene V. Singh、Tracey R. Friss、John C. MacDonald、Shawn C. Burdette

  DOI：10.1039/c2dt30135k

  日期：——

  tridentate ZinCast-1 utilizes a bis-pyridin-2-ylmethyl-aniline ligand that forms a 5,5-chelate ring upon metal binding. The related photocages ZinCast-2 with a N-[2-(pyridine-2-yl)ethyl]-N-(pyridine-2-ylmethyl)aniline (5,6-chelate ring) and ZinCast-3 with a N,N-bis[2-(pyridine-2-yl)ethyl]aniline (6,6-chelate ring) were synthesized for comparative studies. The complexes formed by the ions Cu2+, Zn2+ and

  已经制备并表征了两代用于Zn 2+的基于硝基苯甲酚的光笼。第一个系列包括三齿ZinCast-1，利用双吡啶-2-基甲基苯胺配体，该配体在与金属结合时形成5，5-螯合物环。具有N- [2-（吡啶-2-基）乙基] -N-（吡啶-2-基甲基）苯胺（5,6-螯合物环）的相关光笼ZinCast-2和具有N，N的ZinCast-3合成了双[2-（吡啶-2-基）乙基]苯胺（6,6-螯合物环）用于比较研究。由离子Cu 2 +，Zn 2+和Cd 2+形成的络合物用UV-Vis光谱法分析了三种ZinCast及其光产物（ZinUnc）的混合物。研究表明，ZinCast-1形成具有最高稳定性的复合物，而ZinCast-3在解笼时在金属亲和力方面表现出最显着的变化。这些结果表明，必须考虑氮原子供体能力的变化以及初始配合物的稳定性，以设计具有所需性质的光笼。合成的结果用于设计ZinCast-4和ZinCast-5，这
• 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。
• 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
• US7301049B2
  申请人：——

  公开号：US7301049B2

  公开（公告）日：2007-11-27
• [EN] PHOTOLABILE ESTERS AND THEIR USES<br/>[FR] ESTERS PHOTOLABILES ET LEURS UTILISATIONS
  申请人：CANCER RES INST

  公开号：WO2003000644A1

  公开（公告）日：2003-01-03

  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.