1-(2-nitrophenyl)ethyl carbonochloridate | 154187-40-3

• 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: 1-(2-nitrophenyl)ethyl carbonochloridate
• 英文别名: NPEC-Cl；1-(2-Nitrophenyl)-1-ethoxycarbonyl chloride
• CAS: 154187-40-3
• 化学式: C₉H₈ClNO₄
• 分子量: 229.62
• InChiKey: QRAXFOMREJXVAK-UHFFFAOYSA-N

物化性质

• 沸点：
  336.1±25.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 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：

  1-(2-nitrophenyl)ethyl carbonochloridate 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine
  参考文献：
  名称：

  Synthesis of Photolabile 5′-O-Phosphoramidites for the Photolithographic Production of Microarrays of Inversely Oriented Oligonucleotides

  摘要：

  The photolabile 3 ' -O-{[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' -phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in situ DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the orientation of enzymatic synthesis. Synthesis yields were as good as those of conventional reactions. The resulting oligonucleotides are attached to the: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are available as substrates for enzymatic reactions such as primer extension upon hybridization of a DNA template (see Fig. 2). The production of such oligonucleotide chips adds new procedural avenues to the growing number of applications of DNA microarrays.

  DOI：

  10.1002/1522-2675(20010711)84:7<2089::aid-hlca2089>3.0.co;2-0
• 作为产物：
  描述：

  邻硝基苯乙酮 在 sodium tetrahydroborate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 44.0h， 生成 1-(2-nitrophenyl)ethyl carbonochloridate
  参考文献：
  名称：

  使用光可去除 NPEC 基团合成完全保护的 aculeine B 长链多胺亚基

  摘要：

  多胺在自然界中普遍存在。在本文中，我们公开了用于合成结构定义的 1,3-丙二胺聚合物的迭代偶联策略，该聚合物可用于合成最初提出的结构和从海洋海绵。我们首先尝试使用“Ns 策略”合成多胺，但发现具有 11 个 Ns 基团的多胺存在溶解度问题。然后我们检查了多胺合成中可光去除的 NPEC 保护基团的多功能性。最后，使用 NPEC 基团临时保护末端氨基，实现了适当保护的 12 聚体多胺的合成。

  DOI：

  10.1039/d3ob00369h

文献信息

• Aspartic Acid Forming α-Ketoacid–Hydroxylamine (KAHA) Ligations with (<i>S</i>)-4,4-Difluoro-5-oxaproline
  作者：Simon Baldauf、Ayodele O. Ogunkoya、Gábor N. Boross、Jeffrey W. Bode

  DOI：10.1021/acs.joc.9b02271

  日期：2020.2.7

  The α-ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. Currently, the most applied hydroxylamine is the 5-membered cyclic hydroxylamine (S)-5-oxaproline, which forms a homoserine ester as the primary ligation product. In order to access native aspartic acid residues at the ligation site, we synthesized a 4,4-difluoro version of this monomer. Upon KAHA ligation

  α-酮酸-羟胺（KAHA）连接可以偶联未保护的肽段。当前，最常用的羟胺是5-元环状羟胺（S）-5-氧杂脯氨酸，其形成高丝氨酸酯作为主要的连接产物。为了在连接位点获得天然天冬氨酸残基，我们合成了该单体的4,4-二氟版本。KAHA连接后，生成的二氟醇水解为天冬氨酸残基，几乎没有或没有天冬酰胺形成。我们将该单体用于激素肽胰高血糖素和胰岛素变体的合成，以及肽UbcH5a和SUMO3的片段连接。
• Photoactive materials applicable to imaging systems
  申请人：Agfa-Gevaert

  公开号：US06384264B1

  公开（公告）日：2002-05-07

  Organic photoprecursors of amines are provided for use in photosensitive imaging systems, finding particular application in the preparation of lithographic printing plates. Said photoprecursors generate free amines on exposure to long wavelength UV or visible radiation, have high solubility in organic solvents, and include photolabile 2-nitrobenzyl functional groups. Methods for the synthesis of the photoprecursors are described, and the use of the said photoprecursors for the production of printing plates using both positive working and negative working techniques are discussed.

  提供了有机胺的光敏前体，用于光敏成像系统，特别适用于制备平版印刷版。所述光敏前体在长波长紫外或可见光辐射下产生游离胺，对有机溶剂具有很高的溶解度，并包括光敏2-硝基苯甲基功能基团。描述了合成光敏前体的方法，并讨论了使用所述光敏前体制备印刷版的方法，包括正工作和负工作技术。
• Studies on Aculeines: Synthetic Strategy to the Fully Protected Protoaculeine B, the <i>N</i>-Terminal Amino Acid of Aculeine B
  作者：Hiroki Shiozaki、Masayoshi Miyahara、Kazunori Otsuka、Kei Miyako、Akito Honda、Yuichi Takasaki、Satoshi Takamizawa、Hideyuki Tukada、Yuichi Ishikawa、Ryuichi Sakai、Masato Oikawa

  DOI：10.1021/acs.orglett.8b01331

  日期：2018.6.1

  A synthetic strategy for accessing protoaculeine B (1), the N-terminal amino acid of the highly modified peptide toxin aculeine, was developed via the synthesis of the fully protected natural homologue of 1 with a 12-mer poly(propanediamine). The synthesis of mono(propanediamine) analog 2, as well as core amino acid 3, was demonstrated by this strategy. New amino acid 3 induced convulsions in mice;

  通过合成具有12-mer聚丙二胺1的完全受保护的天然同源物，开发了一种用于获得原球泡蛋白B（1）（高度修饰的肽毒素球泡蛋白的N末端氨基酸）的合成策略。该策略证明了单（丙二胺）类似物2以及核心氨基酸3的合成。新的氨基酸3诱发小鼠惊厥；但是，化合物2没有这种活性。
• Bispecific antibodies in which the binding capability is reversibly inhibited by a photocleavable moiety
  申请人：——

  公开号：US20040197336A1

  公开（公告）日：2004-10-07

  Antibodies are described which can bind to a member of a binding pair and to a macromolecule in which the capability of binding to the macromolecule is reversibly inhibited by the presence of a photocleavable moiety. Favoured antibodies are bispecific antibodies, for example against a tumour cell and against an enzyme or a killer cell in which the capability of binding to the enzyme or the killer cell is inhibited until the photocleavable moiety is removed on irradiation.

  描述了一种能够结合到结合对的成员和到一种大分子的抗体，其中结合到大分子的能力通过光解离性基团的存在而可逆地受到抑制。优选的抗体是双特异性抗体，例如针对肿瘤细胞和针对酶或杀伤细胞的抗体，在这些抗体中，结合到酶或杀伤细胞的能力在光照作用下直到光解离性基团被去除之前都受到抑制。
• Synthesis, Photoreactivity and Cytotoxic Activity of Caged Compounds of L-Leucyl-L-Leucine Methyl Ester, an Apoptosis Inducer
  作者：Mitsuyo Odaka、Toshiaki Furuta、Yoshiro Kobayashi、Michiko Iwamura

  DOI：10.1111/j.1751-1097.1996.tb09633.x

  日期：1996.6

  I,‐Leucyl‐L‐leucine methyl ester (Leu‐Leu‐OMe), an apoptosis inducer in natural killer cells and macro‐phages, was caged with trans‐o‐hydroxycinnamoyl (3ad), trans‐o‐mercaptocinnamoyl (4) and o‐nitrobenzyl derivatives (5a, b), and the photochemical reactivity of these derivatives in phosphate‐buffered saline containing 1% dimethyl sulfoxide and their immunological properties were studied. All of the

  I,-亮氨酰-L-亮氨酸甲酯（Leu-Leu-OMe）是一种自然杀伤细胞和巨噬细胞的凋亡诱导剂，被反式-o-羟基肉桂酰（3ad）、反-o-巯基肉桂酰（4）笼罩和邻硝基苄基衍生物 (5a, b)，并研究了这些衍生物在含有 1% 二甲亚砜的磷酸盐缓冲盐水中的光化学反应性及其免疫学特性。所有衍生物都在比 UVB 区域更长的波长处表现出吸收。尽管预计 3a-d 和 4 会异构化为顺式异构体，该异构体在分子内环化得到 Leu-Leu-OMe 和香豆素衍生物，但除 3a 外，环化效率并不令人满意。然而，3a 本身会导致 U937 细胞（一种骨髓细胞系）的坏死（细胞肿胀）。相比之下，5a 和 b 快速有效地释放 Leu-Leu-OMe，并且不影响 U937 细胞。虽然辐照 5b 诱导了坏死，但辐照 3a 和 5a 会诱导这些细胞凋亡，这由细胞大小的减小所证明。