(2S,4S)-N,N-dimethyl-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide | 115295-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-N,N-dimethyl-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide
• 英文别名: (3S,5S)-1-allyloxycarbonyl-5-dimethylaminocarbonyl-3-mercaptopyrrolidine；(2S,4S)-1-allyloxycarbonyl-2-dimethylaminocarbonyl-4-mercaptopyrrolidine；(2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine；[2S,4S]-1-allyloxycarbonyl-2-dimethylaminocarbonyl-4-mercaptopyrrolidine；(3S,5S)-1-allyloxycarbonyl-5-(N,N-dimethylcarbamoyl)pyrrolidine-3-thiol；prop-2-enyl (2S,4S)-2-(dimethylcarbamoyl)-4-sulfanylpyrrolidine-1-carboxylate
• CAS: 115295-89-1
• 化学式: C₁₁H₁₈N₂O₃S
• 分子量: 258.342
• InChiKey: MYXOQFFIIVIFLU-IUCAKERBSA-N

物化性质

• 沸点：
  394.0±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S)-N,N-dimethyl-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide 在 四(三苯基膦)钯 5,5-二甲基-1,3-环己二酮 、 N,N-二异丙基乙胺 作用下， 生成 4-nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylcarbamoyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxy-ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel carbapenems with a catechol or hydroxypyridone moiety.

  摘要：

  DOI：

  10.7164/antibiotics.47.1354
• 作为产物：
  描述：

  (2S,4S)-N,N-二甲基-1-烯丙氧羰基-4-苯甲酰硫基-2-吡咯烷甲酰胺 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 (2S,4S)-N,N-dimethyl-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide
  参考文献：
  名称：

  实用的新型脱水型Ti-Dieckmann缩合法合成1β-甲基卡巴南

  摘要：

  利用新型脱水类型的Ti-Dieckmann（分子内Ti-Claisen）缩合反应，可以高效，实用且立体控制地合成1β-甲基卡巴姆。与传统的碱性狄克曼缩合反应相比，该环化反应具有将硫醇部分直接掺入目标1β-甲基卡巴南的优点。另一个优点是使用对环境无害的（低毒性和安全的）试剂（TiCl 4和Et 3 N或Bu 3 N）。

  DOI：

  10.1002/adsc.200303065

文献信息

• Beta-lactam compounds, and their production and use
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0472062A1

  公开（公告）日：1992-02-26

  A compound of the formula: which is useful as an antimicrobial agent.

  一个化学式为的化合物，可用作抗微生物剂。
• Processes for preparing carbapenem derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05306816A1

  公开（公告）日：1994-04-26

  The invention relates to carbapenem derivatives useful as antimicrobial agents, more particularly to intermediate compounds for the preparations thereof of the formula ##STR1##

  该发明涉及一种卡那霉素衍生物，可用作抗微生物剂，更特别地，涉及用于其制备的中间化合物，其化学式为##STR1##。
• Pyrrolidine derivatives and process for preparing the same
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US05322952A1

  公开（公告）日：1994-06-21

  Pyrrolidine derivatives of the formula (1): ##STR1## wherein R is a protective group of the amino group, intermediates for constructing the 2-positioned side chain of antibacterial penem and carbapenem compounds, are prepared by allowing ##STR2## to react with active esterifying agents in the presence of a base, further allowing the product to react with hydrogen sulfide in the presence of a base and then treating the product with a base.

  式（1）的吡咯烷衍生物：##STR1## 其中R是氨基保护基，用于构建抗菌青霉烯和碳青霉烯化合物的2-位侧链的中间体，通过在碱的存在下允许 ##STR2## 与活性酯化试剂反应，进一步在碱的存在下允许产物与氢硫化物反应，然后用碱处理产物来制备。
• Experimental and Theoretical Studies on the Reactions of Aliphatic Imines with Isocyanates
  作者：Etienne Cotter、Felix Pultar、Sereina Riniker、Karl‐Heinz Altmann

  DOI：10.1002/chem.202304272

  日期：2024.3.7

  The reaction of isocyanates with imines derived from allyl glycinate and differently substituted propionaldehydes was investigated. For reactions with α,α-dimethylated imines either 2,3-dihydro-4H-1,3,5-oxadiazin-4-ones or 2,4-dioxo-6-(aryl-/alkylthio)tetrahydro-pyrimidines were obtained as major products, which are formed via a [4+2] cycloaddition pathway. In contrast, the formation of 1,3-diazetidinones

  研究了异氰酸酯与源自甘氨酸烯丙酯和不同取代的丙醛的亚胺的反应。对于与 α,α-二甲基化亚胺的反应，得到 2,3-二氢-4 H -1,3,5-恶二嗪-4-酮或 2,4-二氧代-6-(芳基-/烷硫基)四氢-嘧啶作为主要产物，通过[4+2]环加成途径形成。相反，没有观察到通过[2+2]环加成形成1,3-二氮杂环丁酮。通过 DFT 计算使不同的反应结果合理化。
• 4-Substituted alkyl carbapenem antibiotics
  申请人：Bristol-Myers Squibb Company

  公开号：EP0433759A1

  公开（公告）日：1991-06-26

  Compounds of the formula wherein R1 is hydrogen, C1-2 alkyl, -CH20H, -CH2NH2, A is an unsubstituted or hydroxy-substituted straight or branched C, -, 10 alkylene group or a straight or branched C1-10 alkylene group having an intervening heteroatom selected from oxygen, sulfur and nitrogen; R2 is hydroxy, halogen, C1-4 alkoxy, nitrile, azido, a quaternary ammonio group, -NRSR6, azetidinyl, or a 5- or 6-membered heterocyclic group selected from heteroaromatic and heteroalicyclic joined through a carbon atom thereof; B is a straight or branched C, -6 alkylene group or a direct bond when R3 is joined to the sulfur atom through a carbon atom thereof; R3 is a residue of an organic group; R4 is hydrogen, a removable carboxy-protecting group or a physiologically hydrolyzable ester group; R5 and R6 each are independently hydrogen, C1-6 alkyl, C1-4 alkoxy, hydroxyethyl, azidoethyl, aminoethyl, and when R5 is hydrogen or C, -a alkyl, R6 is hydroxy, C1-4 alkoxy, amino, C1-4 alkylamino, di(Ci-4.)alkylamino, substituted C1-4 alkyl wherein said alkyl substituent is selected from hydroxy, azido, amino, guanidino, nitrile, carboxy, formimidoyl and phenyl, or an acyl residue of an amino acid or peptide; or R5 and R6, taken together with the nitrogen atom to which they are attached, is an unsubstituted or substituted heterocyclic ring having 1 to 2 ring members and having up to four heteroatoms in each ring independently selected from oxygen, nitrogen and sulfur, wherein said substituent is selected from the group consisting of C1-4 alkyl, C1-4 alkoxy, trifluoromethyl, hydroxy, halogen, amino, nitrile, carboxy, carbamido, carbamoyl, C, -4 alkylamino and amino (C1-4) alkyl; W is a direct bond, oxygen, sulfur or NR'°; Y is oxygen or NR10; Z is hydrogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, -NR7R8, amino(C1-4)alkyl, azido(C1-4)alkyl or hydroxy (C1-4)alkyl; R7 and R8 each are independently hydrogen, C1-4 alkyl or alkanoyl; and R10 is hydrogen, C1-4 alkyl, C1-4 alkylamino or di(C1-4)alkylamino; or a non-toxic pharmaceutically acceptable salt thereof, are novel antimicrobial agents which are useful in the treatment of infectious disease in humans and other animals. Novel intermediates and processes for their preparation are also disclosed.

  式中的化合物 其中 R1 为氢、C1-2 烷基、-CH20H、-CH2NH2、 A 是未取代的或羟基取代的直链或支链 C,-,10-亚烷基，或具有选自氧、硫和氮的杂原子的直链或支链 C1-10 亚烷基； R2 是羟基、卤素、C1-4 烷氧基、腈、叠氮、季铵基、-NRSR6、 氮杂环丁基，或通过一个碳原子连接的 5 或 6 元杂环基团，这些杂环基团选自杂芳族和杂脂环； B 是直链或支链 C, -6 亚烷基，或当 R3 通过其碳原子与硫原子相连时的直接键； R3 是有机基团的残基； R4 是氢、可去除的羧基保护基团或生理上可水解的酯基； R5和R6各自独立地是氢、C1-6烷基、C1-4烷氧基、羟乙基、叠氮乙基、氨基乙基，当R5是氢或C, -a烷基时，R6是羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4.当 R5 为氢或 C-a烷基时，R6 为羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4. )烷基氨基、取代的 C1-4 烷基，其中所述烷基取代基选自羟基、叠氮基、氨基、胍基、腈基、羧基、甲酰亚胺基和苯基，或氨基酸或肽的酰基残基；或 R5 和 R6，连同它们所连接的氮原子，是一个未取代或取代的杂环，具有 1 至 2 个环成员，且每个环中具有最多 4 个独立选自氧、氮和硫的杂原子，其中所述取代基选自由 C1-4 烷基、C1-4 烷氧基、三氟甲基、羟基、卤素、氨基、腈、羧基、氨基甲酰基、氨基甲酰基、C, -4 烷基氨基和氨基（C1-4）烷基组成的组；W 是直接键、氧、硫或 NR'°； Y 是氧或 NR10 Z 是氢、羟基、C1-4 烷基、C1-4 烷氧基、-NR7R8、氨基（C1-4）烷基、叠氮（C1-4）烷基或羟基（C1-4）烷基； R7 和 R8 各自独立地为氢、C1-4 烷基或烷酰基；以及 R10 是氢、C1-4 烷基、C1-4 烷基氨基或二(C1-4)烷基氨基； 或其无毒药学上可接受的盐，是新型抗菌剂，可用于治疗人类和其他动物的传染性疾病。此外，还公开了新型中间体及其制备工艺。