4-(Hydroxymethyl)-3-nitrobenzoic acid 2,4,5-trichlorophenyl ester | 130581-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(Hydroxymethyl)-3-nitrobenzoic acid 2,4,5-trichlorophenyl ester
• 英文别名: 2,4,5-trichlorophenyl 4-hydroxymethyl-3-nitrobenzoate；2,4,5-Trichlorophenyl 4-(hydroxymethyl)-3-nitrobenzoate；(2,4,5-trichlorophenyl) 4-(hydroxymethyl)-3-nitrobenzoate
• CAS: 130581-93-0
• 化学式: C₁₄H₈Cl₃NO₅
• 分子量: 376.58
• InChiKey: OEOOZPHQSPNDSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(Hydroxymethyl)-3-nitrobenzoic acid 2,4,5-trichlorophenyl ester 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.25h， 生成 (2,4,5-trichlorophenyl) 4-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxycarbonyloxymethyl]-3-nitrobenzoate
  参考文献：
  名称：

  Cleavage of Oligonucleotides from Solid-Phase Supports Using o-Nitrobenzyl Photochemistry

  摘要：

  Oligonucleotides are cleaved from modified solid phase supports using the o-nitrobenzylintramolecular photochemical redox reaction. Oligonucleotides can be cleaved before or after removal of protecting groups. Employment of phosphoramidites containing allyloxy protecting groups that are labile to Pd-O enables one to deprotect oligonucleotides without the use of base. The yields of isolated oligonucleotides relative to yields obtained using conventional hydrolytic cleavage vary between 59% and 87%. Tritium labeling indicates that small amounts of thymidine thymidine photodimers are formed during the photolysis time required to obtain good yields of oligonucleotides from the succinate linked photolabile support (4). Photodimer formation is minimized (<7%) during the prolonged irradiation required when cleaving oligonucleotides from 7 by employing bandpass filtering.

  DOI：

  10.1021/jo00083a014
• 作为产物：
  描述：

  4-溴甲基-3-硝基苯甲酸 在 水 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 4-(Hydroxymethyl)-3-nitrobenzoic acid 2,4,5-trichlorophenyl ester
  参考文献：
  名称：

  聚合固相肽合成。X.使用光不稳定的Nbb树脂合成和纯化受保护的肽片段

  摘要：

  对应于子宫珠蛋白单体的12-18、31-38和59-67片段的受保护肽片段是在光不稳定的邻硝基苄基单元作为手柄的情况下在固相支持物上合成的。序列的第一个氨基酸的连接已经以三种不同的方式进行，并且描述了一种避免在第三种氨基酸与该树脂手柄的偶联中形成DKP的新方法。肽与固相支持物的光解分离以良好的产率发生。尽管它们在反相MPLC和HPLC技术中使用的常规溶剂中溶解度较低，但是可以通过MPLC使用含有高比例DMF的溶剂纯化受保护的肽片段。

  DOI：

  10.1016/s0040-4020(01)80724-9

文献信息

• Photochemical release of protected oligonucleotides containing 3′-glycolate termini
  作者：Marc M. Greenberg

  DOI：10.1016/0040-4020(94)00946-r

  日期：1995.1

  Protected oligonucleotides containing 3′-glycolate termini that are suitable for further elaboration are released from their solid phase supports using the o-nitrobenzyl intramolecular photochemical redox reaction. The yields of isolated oligonucleotides of varying sequence, ranging between 12 and 20 nucleotides long are between 45% and 79%, under conditions that have been previously shown to form

  使用邻硝基苄基分子内光化学氧化还原反应，从固相支持物中释放出适于进一步加工的含有3'-乙醇酸末端的受保护的寡核苷酸。在先前已证明形成少于2％的胸腺嘧啶·胸腺嘧啶光二聚体的条件下，长度介于12至20个核苷酸之间的可变序列的分离寡核苷酸的产率在45％至79％之间。
• Convergent solid-phase peptide synthesis. X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin
  作者：Paul Lloyd-Williams、Margarida Gairí、Fernando Albericio、Ernest Giralt

  DOI：10.1016/s0040-4020(01)80724-9

  日期：1991.12

  Protected peptide fragments corresponding to the 12–18, 31–38 and 59–67 segments of the Uteroglobin monomer have been synthesised on a solid support using the photolabile ortho-nitrobenzyl unit as a handle. Attachment of the first amino acid of the sequence has been carried out in three different ways and a new procedure for avoiding the formation of DKPs in the coupling of the third amino acid with

  对应于子宫珠蛋白单体的12-18、31-38和59-67片段的受保护肽片段是在光不稳定的邻硝基苄基单元作为手柄的情况下在固相支持物上合成的。序列的第一个氨基酸的连接已经以三种不同的方式进行，并且描述了一种避免在第三种氨基酸与该树脂手柄的偶联中形成DKP的新方法。肽与固相支持物的光解分离以良好的产率发生。尽管它们在反相MPLC和HPLC技术中使用的常规溶剂中溶解度较低，但是可以通过MPLC使用含有高比例DMF的溶剂纯化受保护的肽片段。
• Cleavage of Oligonucleotides from Solid-Phase Supports Using o-Nitrobenzyl Photochemistry
  作者：Marc M. Greenberg、John L. Gilmore

  DOI：10.1021/jo00083a014

  日期：1994.2

  Oligonucleotides are cleaved from modified solid phase supports using the o-nitrobenzylintramolecular photochemical redox reaction. Oligonucleotides can be cleaved before or after removal of protecting groups. Employment of phosphoramidites containing allyloxy protecting groups that are labile to Pd-O enables one to deprotect oligonucleotides without the use of base. The yields of isolated oligonucleotides relative to yields obtained using conventional hydrolytic cleavage vary between 59% and 87%. Tritium labeling indicates that small amounts of thymidine thymidine photodimers are formed during the photolysis time required to obtain good yields of oligonucleotides from the succinate linked photolabile support (4). Photodimer formation is minimized (<7%) during the prolonged irradiation required when cleaving oligonucleotides from 7 by employing bandpass filtering.