N-p-nitrobenzyloxycarbonylazetidinethiol | 86063-68-5

• 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: N-p-nitrobenzyloxycarbonylazetidinethiol
• 英文别名: N-p-nitrobenzyloxycarbonyl-3-mercaptoazetidine；(4-Nitrophenyl)methyl 3-sulfanylazetidine-1-carboxylate
• CAS: 86063-68-5
• 化学式: C₁₁H₁₂N₂O₄S
• 分子量: 268.293
• InChiKey: AIUOVNQALUZMGX-UHFFFAOYSA-N

物化性质

• 沸点：
  446.4±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-p-nitrobenzyloxycarbonylazetidinethiol 、 (4R,5R,6R)-3-(Diphenoxy-phosphoryloxy)-4-methyl-6-methylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以84%的产率得到(4R,5R,6R)-4-Methyl-6-methylsulfanyl-3-[1-(4-nitro-benzyloxycarbonyl)-azetidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of New Non-natural 1b-Methylcarbapenems Bearing Methylthio Group at the C6-Position

  摘要：

  The asymmetric total synthesis of new non-natural 1-beta-methylcarbapenems (1 and 2) has been accomplished starting from optically active C4-substituted azetidin-2-one (4).

  DOI：

  10.3987/com-91-s85
• 作为产物：
  描述：

  3-hydroxy-1-(p-nitrobenzyloxycarbonyl)azetidine 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-p-nitrobenzyloxycarbonylazetidinethiol
  参考文献：
  名称：

  Asymmetric Synthesis of New Non-natural 1b-Methylcarbapenems Bearing Methylthio Group at the C6-Position

  摘要：

  The asymmetric total synthesis of new non-natural 1-beta-methylcarbapenems (1 and 2) has been accomplished starting from optically active C4-substituted azetidin-2-one (4).

  DOI：

  10.3987/com-91-s85

文献信息

• Penem derivatives and antimicrobial agents containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0774465A1

  公开（公告）日：1997-05-21

  Penem derivatives represented by the following Formula (I): wherein Z represents a hydroxyl group or a fluorine atom, R1 represents a substituted or unsubstituted alkyl, alkenyl, aralkyl group, aryl group, heterocyclic, or acyl group, or a hydrogen atom, and R2 represents a hydrogen atom or a carboxyl-protecting group; and pharmacologically acceptable salts thereof are antibacterial agents effective against, inter alia, methicillin-resistant Staphylococcus aureus. The derivatives and salts are novel except when R1 is ethyl and Z is hydroxyl. The analogous compounds in which R2 is a carboxyl-protecting group and any hydroxyl group represented by Z is protected are novel process intermediates.

  Penem衍生物由以下公式（I）表示：其中Z代表一个羟基团或氟原子，R1代表一个取代或未取代的烷基，烯基，芳基甲基，芳基，杂环基或酰基，或氢原子，R2代表一个氢原子或羧基保护基；及其药理学上可接受的盐是有效的抗菌剂，可用于治疗耐甲氧西林金黄色葡萄球菌等感染。这些衍生物和盐是新颖的，除非R1是乙基且Z是羟基。其中R2是羧基保护基且Z代表的任何羟基被保护的类似化合物是新颖的工艺中间体。
• Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0536936A1

  公开（公告）日：1993-04-14

  Compounds of formula (I): [in which: R¹, R² and R³ are the same or different and each represents a hydrogen atom, an optionally substituted alkanoyl group or an alkenylcarbonyl group, provided that at least one of R¹, R² and R³ represents an unsubstituted alkanoyl group having from 5 to 24 carbon atoms, said substituted alkanoyl group or said alkenylcarbonyl group; and one of R⁴ and R⁵ represents a hydrogen atom and the other represents a cyano group]; have valuable anti-tumour activity.

  式子（I）的化合物：[其中：R¹、R²和R³相同或不同，每个代表氢原子、可选取代的脂肪酰基团或烯基羰基团，前提是至少有一个R¹、R²和R³代表有5到24个碳原子的未取代脂肪酰基团，或者是所述取代的脂肪酰基团或所述烯基羰基团；R⁴和R⁵中的一个代表氢原子，另一个代表氰基]，具有有价值的抗肿瘤活性。
• Penem derivatives and antimicrobial agent containing the same
  申请人：Ishiguro Masaji

  公开号：US20050004092A1

  公开（公告）日：2005-01-06

  A penem derivative represented by the following formula (I): wherein R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R 2 represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be-effective.

  以下是公式（I）所代表的一种青霉烷衍生物： 其中，R1代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷基硫基、取代或未取代的烯基硫基、取代或未取代的芳基烷基硫基、取代或未取代的芳基硫基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的酰基硫基、巯基或氢原子，R2代表氢原子或羧酸保护基；或其药学上可接受的盐。该化合物（I）表现出强大的抗菌活性，特别是对MRSA表现出强大的活性。因此，它不仅有用作一般抗菌剂，还有用作抗MRSA的抗菌剂，对于这种细菌，一般的抗菌剂被认为无效。
• Carbapenem derivatives, their preparation and compositions containing them
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0072710A1

  公开（公告）日：1983-02-23

  Compounds of formula (I): [wherein: RI represents a hydrogen atom, an alkyl group, an alkoxy group or various substituted alkyl groups; R2 represents a group of formula in which represents an alicyclic amine group having from 4 to 8 ring atoms, optionally having a single double bond, optionally containing an additional hetero-atom and optionally having an oxo group on the ring; X represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylsulphinyl group, an alkylsulphonyl group, a hydroxy group, a halogen atom or various substituted alkyl groups; Y represents a hydrogen atom, an alkyl group, an aliphatic acyl group or an acylimidoyl group; and R3 represents a carboxy group or a protected carboxy group] and pharmaceutically acceptable salts thereof have valuable antibacterial activity, especially in vivo.

  式(I)化合物： 其中 RI 代表氢原子、烷基、烷氧基或各种取代的烷基； R2 代表式（I）的基团 其中 代表具有 4 至 8 个环原子的脂环胺基团，可选择具有单双键，可选择含有一个额外的杂原子，可选择在环上具有一个氧代基团； X 代表氢原子、烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、羟基、卤素原子或各种取代的烷基； Y 代表氢原子、烷基、脂肪族酰基或酰亚胺酰基；以及 R3 代表羧基或受保护的羧基]。 及其药学上可接受的盐类具有重要的抗菌活性，尤其是在体内。
• Process for the desilylation of a 4-silyloxy-tetrahydro-pyran-2-one
  申请人：MERCK & CO. INC.

  公开号：EP0444888A1

  公开（公告）日：1991-09-04

  A process is described for the removal of a silyl protecting group from the 4-hydroxy group of a tetrahydro-pyran-2-one moiety.

  描述了一种从四氢吡喃-2-酮分子的 4-羟基上去除硅烷保护基的工艺。