N-(苄氧基羰基氧基)-邻苯二甲酰亚胺 | 65162-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-(苄氧基羰基氧基)-邻苯二甲酰亚胺
• 英文名称: N-(benzyloxycarbonyloxy)succinimide
• 英文别名: N-(benzyloxycarbonyloxy)phthalimide；N-(Benzyloxycarbonyloxy)-phthalimide；benzyl (1,3-dioxoisoindol-2-yl) carbonate
• CAS: 65162-83-6
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: QHZNYGVZDCMWKX-UHFFFAOYSA-N

物化性质

• 沸点：
  452.5±38.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  尼拉霉素 、 N-(苄氧基羰基氧基)-邻苯二甲酰亚胺 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以64%的产率得到6'-N-benzyloxycarbonyltobramycin
  参考文献：
  名称：

  Synthesis and Biological Activity of Mono- and Di-N-acylated Aminoglycosides

  摘要：

  Despite issues with oto/nephrotoxicity and bacterial resistance, aminoglycosides (AGs) remain an effective and widely used class of antibacterial agents. For decades now, efforts toward the development of novel AGs with potential to overcome some of these problems have been major research focuses. 1-N-Acylation, especially gamma-amino-beta-hydroxybutyrate (AHB) derivatization, has proven to be one of the most successful strategies for improving the overall properties of AGs, including their ability to avoid certain resistance mechanisms. More recently, 6'-N-acylation arose as another possible strategy to improve the properties of these drugs. In this study, we report on the glycinyl, carboxybenzyl, and AHB mono- and diderivatization at the 1-, 6'-, and/or 4'''-amines of the AGs amikacin, kanamycin A, netilmicin, sisomicin, and tobramycin. We also present the antibacterial activities and the reduced reactivity of AG-modifying enzymes (AMEs) toward these new AG derivatives, and identify the AMEs present in the bacterial strains tested.

  DOI：

  10.1021/acsmedchemlett.5b00255
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 氯甲酸苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到N-(苄氧基羰基氧基)-邻苯二甲酰亚胺
  参考文献：
  名称：

  Synthesis and Biological Activity of Mono- and Di-N-acylated Aminoglycosides

  摘要：

  Despite issues with oto/nephrotoxicity and bacterial resistance, aminoglycosides (AGs) remain an effective and widely used class of antibacterial agents. For decades now, efforts toward the development of novel AGs with potential to overcome some of these problems have been major research focuses. 1-N-Acylation, especially gamma-amino-beta-hydroxybutyrate (AHB) derivatization, has proven to be one of the most successful strategies for improving the overall properties of AGs, including their ability to avoid certain resistance mechanisms. More recently, 6'-N-acylation arose as another possible strategy to improve the properties of these drugs. In this study, we report on the glycinyl, carboxybenzyl, and AHB mono- and diderivatization at the 1-, 6'-, and/or 4'''-amines of the AGs amikacin, kanamycin A, netilmicin, sisomicin, and tobramycin. We also present the antibacterial activities and the reduced reactivity of AG-modifying enzymes (AMEs) toward these new AG derivatives, and identify the AMEs present in the bacterial strains tested.

  DOI：

  10.1021/acsmedchemlett.5b00255

文献信息

• Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation
  作者：Yu-Lan Zhang、Lei Yang、Jie Wu、Chunyin Zhu、Peng Wang

  DOI：10.1021/acs.orglett.0c03074

  日期：2020.10.2

  Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative alkenylation with vinyl sulfonium salts was realized using eosin Y as a photocatalyst. This process features

  乙烯基sulf盐通常充当亲电的迈克尔受体，因此引发许多串联环化反应。在这里，我们公开了乙烯基sulf盐作为自由基受体的新型反应性。使用氧化还原活性酯作为烷基自由基前体，使用曙红Y作为光催化剂实现了带有乙烯基sulf盐的无金属脱羧烯基化。该方法具有广泛的底物范围，并能耐受多种伯，仲，叔羧酸。
• New potent C 2 -Symmetric malaria plasmepsin I and II inhibitors
  作者：Karin Oscarsson、Stefan Oscarson、Lotta Vrang、Elizabeth Hamelink、Anders Hallberg、Bertil Samuelsson

  DOI：10.1016/s0968-0896(02)00643-0

  日期：2003.4

  plasmepsin (Plm) I and II inhibitors containing a C(2)-symmetric core structure have been synthesised and tested for protease inhibition activity. These compounds can be prepared using a straightforward synthesis involving a phenol nucleophilic ring opening of a diepoxide. Exemplar compounds synthesised exhibited remarkable inhibitory activity against both Plm I and II, notably 15c with K(i) values of 2

  已经合成了一系列含有C（2）对称核心结构的疟疾纤溶酶（Plm）I和II抑制剂，并测试了其蛋白酶抑制活性。这些化合物可以使用涉及二环氧的酚亲核开环的直接合成来制备。合成的示例化合物对Plm I和II均显示出显着的抑制活性，尤其是15c，其K（i）值分别为2.7nM和0.25nM，并且对组织蛋白酶D的选择性超过100倍。
• Synthesis of 6(S)-amino-7-cyclohexyl-4,4-difluoro-3(R),5(R)-dihydroxy-2-methyiheptane, a novel dipeptide mimic
  作者：Hing L. Sham、Cheryl A. Rempel、Herman Stein、Jerome Cohen

  DOI：10.1039/c39900000904

  日期：——

  The incorporation of the novel dipeptide mimic (1), synthesized via Boc-L-cyclohexylalaninol (Boc = t-butoxycarbonyl), into a dipeptide sequence has led to a very potent renin inhibitor.

  通过Boc- L-环己基丙氨醇（Boc =叔丁氧羰基）合成的新型二肽模拟物（1）掺入二肽序列已产生非常有效的肾素抑制剂。
• 一种硫酸依替米星的制备方法
  申请人：福安药业集团宁波天衡制药有限公司

  公开号：CN108409814A

  公开（公告）日：2018-08-17

  本发明涉及一种硫酸依替米星的制备方法，包括以下步骤：取庆大霉素C1a碱，溶于一定比例的溶剂中，加入一定比例的络合剂，加入一定比例的氨基保护剂维持一定时间，加入一定比例的溶剂和氨水，搅拌、分液、浓缩，得第一中间体；取一定比例的还原剂，加入一定比例的溶剂和乙酸，维持一定时间，再加入第一中间体，反应一段时间，加入强碱溶液调pH，过滤、浓缩，得第二中间体；再加入一定比例的溶剂和钯碳催化剂，在一定氢压、温度下反应，过滤、浓缩，树脂吸附，用氨水解析，再浓缩、硫酸调pH、碳脱、过滤、干燥即得到硫酸依替米星。
• Aminoglycoside antibiotic compounds
  申请人：Schering Corporation

  公开号：US04230847A1

  公开（公告）日：1980-10-28

  Selective blocking of some amino groups in a polyamino organic compound having at least one pair of available neighboring hydroxyl and amino groups is effected by first preparing in situ transition metal salt complexes of available neighboring amino and hydroxyl group pairs in said polyamino organic compound, followed by introduction of blocking groups on the non-complexed amino groups and, finally, removing the transition metal cations from the selectively N-blocked polyamino organic compound complex to obtain a polyamino organic compound having selectively blocked amino groups. This process is particularly valuable when carrying out aminocyclitol-aminoglycoside transformations utilizing transition metal salt complexes of cupric acetate, nickel (II) acetate, cobalt (II) acetate or mixtures thereof.

  在至少具有一对可用相邻羟基和氨基的多氨基有机化合物中，通过首先制备所述多氨基有机化合物中可用的相邻氨基和羟基对的原位过渡金属盐络合物，然后在非络合氨基上引入阻断基，最后从选择性N-阻断的多氨基有机化合物络合物中去除过渡金属阳离子，以获得具有选择性阻断氨基的多氨基有机化合物。当使用乙酸铜、乙酸镍（II）、乙酸钴（II）或其混合物的过渡金属盐络合物进行氨基环糖苷转化时，此过程特别有价值。