N-<α-(tert-Butoxycarbonyl)-benzyloxy>-phthalimid | 56846-71-0

• 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
• 英文名称: N-<α-(tert-Butoxycarbonyl)-benzyloxy>-phthalimid
• 英文别名: N-[α-(t-butoxycarbonyl)-benzyloxy] phthalimide；N-[alpha-(t-butoxycarbonyl) benzyloxy] phthalimide；tert-butyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-phenylacetate
• CAS: 56846-71-0
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: WHIGPILZMGCQKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2-溴-2-苯基乙酸叔丁酯 、 二甲基亚砜 在 potassium carbonate 作用下， 以78%的产率得到N-<α-(tert-Butoxycarbonyl)-benzyloxy>-phthalimid
  参考文献：
  名称：

  3-Acetoxymethyl cephalosporins having at position-7 a carboxy

  摘要：

  这种3-乙酰氧甲基头孢菌素抗生素，其中7-β-酰胺基团具有结构##STR1## 其中R是噻吩基、呋喃基或苯基；R.sup.a是C.sub.1-4烷基、C.sub.2-4烯基、C.sub.3-7环烷基或苯基，R.sup.b是氢、羧基、C.sub.2-C.sub.5羰基酯或R.sup.a指定的任何基团，或R.sup.a和R.sup.b与它们连接的碳原子一起形成C.sub.3-7环烷基亚甲基或环烯基亚甲基团；表现出广谱抗生素活性，特别是对革兰氏阴性微生物具有极高的活性，包括那些产生β-内酰胺酶的。这些化合物是同构体或存在至少90%同构体的同和反异构体的混合物，对大肠杆菌、流感嗜血杆菌和变形杆菌菌株表现出特别高的体外活性；并且还表现出对铜绿假单胞菌具有异常高的活性。

  公开号：

  US04144393A1

文献信息

• 3-Carbamoyloxymethyl or
  申请人：Glaxo Laboratories Limited

  公开号：US04095021A1

  公开（公告）日：1978-06-13

  Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## (where R is thienyl or furyl; R.sup.a and R.sup.b are each selected from hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C.sub.2-5 alkoxycarbonyl and cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; and m and n are each 0 or 1 such that the sum of m and n is 0 or 1) exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; compounds wherein at least one of R.sup.a and R.sup.b is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the above type include those in which the 7.beta.-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetamido group.

  7-β-酰胺基头孢菌素，其结构中的7-β-酰胺基团具有以下结构：##STR1##（其中R为噻吩基或呋喃基；R.sup.a和R.sup.b分别选自氢，C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基，苯基，萘基，噻吩基，呋喃基，羧基，C.sub.2-5烷氧基羰基和氰基，或R.sup.a和R.sup.b与它们附着的碳原子形成C.sub.3-7环烷基亚甲基或环烯基亚甲基基团；m和n各为0或1，使m和n的和为0或1），表现出广谱抗生素活性，特别是对革兰氏阴性微生物，包括产生β-内酰胺酶的微生物具有特别高的活性。这些化合物是同构体或存在于至少90％为同构体的同和反异构体混合物，对大肠杆菌，流感嗜血杆菌和变形杆菌的菌株具有特别高的体外活性；其中至少有一个R.sup.a和R.sup.b不是氢的化合物也表现出对铜绿假单胞菌的异常高活性。上述类型的重要化合物包括其中7-β-酰胺基团为同-2-羧甲氧基-2-（呋喃-2-基）乙酰氨基，同-2-（2-羧基丙-2-氧基亚氨基）-2-（呋喃-2-基）乙酰氨基或同-2-（1-羧环戊-1-氧基亚氨基）-2-（呋喃-2-基）乙酰氨基基团的化合物。
• 7-(Carboxy substituted .alpha.-etherified oximino arylacetamido)
  申请人：Glaxo Laboratories Limited

  公开号：US04103084A1

  公开（公告）日：1978-07-25

  Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## (where R is thienyl or furyl; R.sup.a and R.sup.b are each selected from hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C.sub.2-5 alkoxycarbonyl and cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; and m and n are each 0 or 1 such that the sum of m and n is 0 or 1) exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; compounds wherein at least one of R.sup.a and R.sup.b is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the above type include those in which the 7.beta.-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetamido group.

  7-β-酰胺基头孢菌素，其结构中7-β-酰胺基团具有以下结构：##STR1##（其中R为噻吩基或呋喃基；R.sup.a和R.sup.b分别选自氢，C.sub.1-4烷基，C.sub.2-4烯基，C.sub.3-7环烷基，苯基，萘基，噻吩基，呋喃基，羧基，C.sub.2-5烷氧羰基和氰基，或R.sup.a和R.sup.b与它们附着的碳原子形成C.sub.3-7环烷基亚甲基或环烯基亚甲基；m和n分别为0或1，使m和n的和为0或1），表现出广谱抗生素活性，其特点是对革兰氏阴性微生物特别高效，包括产生β-内酰胺酶的微生物。这些化合物是同构体或存在至少90％的同构体和反构体的混合物，对大肠杆菌，流感嗜血杆菌和变形杆菌菌株的体外活性特别高；其中R.sup.a和R.sup.b中至少有一个不是氢的化合物也显示出对假单胞菌的异常高活性。上述类型的重要化合物包括其中7-β-酰胺基团为syn-2-羧甲氧基-2-（呋喃-2-基）乙酰胺基，syn-2-（2-羧基丙-2-氧基亚胺）-2-（呋喃-2-基）乙酰胺基或syn-2-（1-羧基环戊-1-氧基亚胺）-2-（呋喃-2-基）乙酰胺基团的化合物。
• Cephem and cepham compounds, processes for their preparation, pharmaceutical compositions containing them
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0013762A2

  公开（公告）日：1980-08-06

  Cephem and Cepham compounds of the formula: wherein R1 is amino or a protected amino, R2 is hydrogen or certain substituent. R3 is hydrogen or lower alkyl, R4 is hydrogen or certain substituent, Rs is carboxy or a protected carboxy and the heavy solid line means single or double-bond and pharmaceutically acceptable salt thereof and processes for their preparation, and also an antibacterial composition comprising, as an effective ingredient, the above compound in association with a pharmaceutically acceptable, substantially nontoxic carrier or excipient. The invention also relates to the starting compounds and their preparation.

  式中的 Cephem 和 Cepham 化合物： 式中 R1 是氨基或受保护的氨基、 R2 是氢或某些取代基 R3 是氢或低级烷基、 R4 是氢或某些取代基、 Rs 是羧基或受保护的羧基 重实线表示单键或双键及其药学上可接受的盐和它们的制备工艺，以及一种抗菌组合物，其有效成分包括上述化合物与药学上可接受的、基本上无毒的载体或赋形剂。本发明还涉及起始化合物 及其制备。
• Starting compounds for preparing cephem compounds and processes for their preparation
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0064582B1

  公开（公告）日：1985-12-11
• US4103084A
  申请人：——

  公开号：US4103084A

  公开（公告）日：1978-07-25