l(-)-N-p-nitrobenzyloxycarbonylproline | 105458-95-5

• 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: l(-)-N-p-nitrobenzyloxycarbonylproline
• 英文别名: 1-(4-nitro-benzyloxycarbonyl)-L-proline；1-(4-Nitro-benzyloxycarbonyl)-L-prolin；1-(4-nitrobenzyloxycarbonyl)-L-proline；(2S)-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carboxylic acid
• CAS: 105458-95-5
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: GFVDJYNCILVSQW-NSHDSACASA-N

物化性质

• 沸点：
  523.1±50.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  l(-)-N-p-nitrobenzyloxycarbonylproline 在 硫化氢 、 三乙胺 、 silver(l) oxide 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-Pyrrolidinecarboxylic acid, 2-[(thiocarboxy)methyl]-,1-[(4-nitrophenyl)methyl] ester, (S)-
  参考文献：
  名称：

  从青霉素到青霉素和碳青霉烯。七。青霉烯衍生物的合成及其抗菌活性。

  摘要：

  由6-氨基青霉烷酸有效地制备了在C-3位具有(R)-羟乙基取代基的氮杂环丁酮衍生物(6)。由二溴仲衍生物(10)，得到相同类型的化合物(16和17)，但为dl-形式。化合物6和16与各种硫代羧酸反应得到青霉烯类衍生物(23a-n)。测定了这些青霉烯类衍生物对各种微生物的最低抑菌浓度值，并讨论了其构效关系。

  DOI：

  10.1248/cpb.34.999
• 作为产物：
  描述：

  对硝基苯甲醇 在 1,4-二氧六环 、 sodium hydroxide 作用下， 生成 l(-)-N-p-nitrobenzyloxycarbonylproline
  参考文献：
  名称：

  The Application of p-Nitrobenzyl Chloroformate to Peptide Synthesis

  摘要：

  DOI：

  10.1021/ja01135a030

文献信息

• 1- Methylcarbapenem derivatives
  申请人：Sankyo Company, Limited

  公开号：US06090802A1

  公开（公告）日：2000-07-18

  A 1-methylcarbapenem compound represented by the following formula (I): ##STR1## wherein R.sup.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 represents hydrogen or an ester residue; and A represents a group of the formula (A1) ##STR2## wherein n is 0, 1 or 2, P is 0, 1 or 2, R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sup.4 is a group (Q2) ##STR3## wherein B is phenylene, phenylene(C.sub.1 -C.sub.3)alkyl, cyclohexylene, cyclohexylene(C.sub.1 -C.sub.3)alkyl or C.sub.1 -C.sub.5 alkylene, R.sup.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sup.14 is a group --C(.dbd.NH)R.sup.8, wherein R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl or a group --NR.sup.9 R.sup.10, wherein R.sup.9 and R.sup.10 are the same or different and are hydrogen or C.sub.1 -C.sub.4 alkyl; or a pharmacologically acceptable salt thereof.

  一种由以下化学式（I）表示的1-甲基碳青霉烯类化合物：其中R.sup.1代表氢或C.sub.1 -C.sub.4烷基；R.sup.2代表氢或酯基；A代表以下化学式（A1）的基团：其中n为0、1或2，P为0、1或2，R.sup.3为氢或C.sub.1 -C.sub.4烷基，R.sup.4为基团（Q2）：其中B为苯基、苯基（C.sub.1 -C.sub.3）烷基、环己基、环己基（C.sub.1 -C.sub.3）烷基或C.sub.1 -C.sub.5烷基，R.sup.7为氢或C.sub.1 -C.sub.4烷基，R.sup.14为基团--C(.dbd.NH)R.sup.8，其中R.sup.8为氢或C.sub.1 -C.sub.4烷基或基团--NR.sup.9 R.sup.10，其中R.sup.9和R.sup.10相同或不同，为氢或C.sub.1 -C.sub.4烷基；或其药理学上可接受的盐。
• Process for producing 1H-3-aminopyrrolidine and derivatives thereof
  申请人：Mitsubishi Chemical Corporation

  公开号：US20020042523A1

  公开（公告）日：2002-04-11

  A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R′NH 2 , subjecting the reaction product to cyclodehydration to obtain an optically active 1 -aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

  公开了一种生产1H-3-氨基吡咯烷及其衍生物的方法。该方法特别适用于生产光学活性的1H-3-氨基吡咯烷及其衍生物，其中包括将公式（1）表示的光学活性氨基保护的天冬氨酸酐与公式R'NH2表示的一级胺反应，将反应产物经过环化脱水作用得到公式（2）表示的光学活性1-芳基甲基-3-(保护氨基)吡咯烷-2,5-二酮化合物，随后消除公式（2）所表示的化合物中3位氨基基团的保护基，得到公式（3）表示的光学活性1-芳基甲基-3-氨基吡咯烷-2,5-二酮化合物，将公式（3）所表示的化合物的羰基基团还原，得到公式（4）表示的光学活性1-芳基甲基-3-氨基吡咯烷化合物或其与质子酸的盐，然后将公式（4）所表示的化合物或其盐进行氢解，得到光学活性的1H-3-氨基吡咯烷或其质子酸盐。
• 1-METHYLCARBAPENEM DERIVATIVES
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0882728A1

  公开（公告）日：1998-12-09

  [Constitution] A 1-methylcarbapenem compound represented by the following formula (I): wherein R1 represents a hydrogen atom or a lower alkyl group; R2 represents a hydrogen atom or an ester residue; and A represents a substituted prolylaminopyrrolidin-1-ylcarbonyl, substituted aminoalkanoylaminopyrrolidin-1-ylcarbonyl, 1-hydroxy-2-(substituted aminoalkylpyrrolidin-1-ylcarbonyl)ethyl, 1-hydroxy-2-(substituted piperazin-1-ylcarbonyl)ethyl, 1-hydroxy-2-(substituted pyrrolidinylaminocarbonyl)ethyl or the like; or a pharmacologically acceptable salt thereof. [Advantages] 1-Methylcarbapenem compounds of the present invention have excellent antibacterial activity and they are useful agents for the prevention or treatment of infectious diseases.

  [组织结构］ 由下式(I)代表的1-甲基碳青霉烯类化合物： 其中 R1 代表氢原子或低级烷基；R2 代表氢原子或酯残基；A代表取代的脯氨酰氨基吡咯烷-1-基羰基、取代的氨基烷酰基氨基吡咯烷-1-基羰基、1-羟基-2-(取代的氨基烷基吡咯烷-1-基羰基)乙基、1-羟基-2-(取代的哌嗪-1-基羰基)乙基、1-羟基-2-(取代的吡咯烷氨基羰基)乙基或类似物；或其药理上可接受的盐。 优势 本发明的 1-甲基碳青霉烯化合物具有优异的抗菌活性，是预防或治疗传染性疾病的有效药物。
• Process for producing 1H-3-aminopyrrolidine and derivatives thereof
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1188744A1

  公开（公告）日：2002-03-20

  A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R'NH2, subjecting the reaction product to cyclodehydration to obtain an optically active 1-aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

  本发明公开了一种生产 1H-3-氨基吡咯烷及其衍生物的工艺。该工艺特别适用于生产具有光学活性的 1H-3-氨基吡咯烷及其衍生物，在这种情况下，该工艺包括将式（1）所代表的具有光学活性的氨基保护天冬氨酸酐与式 R'NH2 所代表的伯胺反应，使反应产物进行环脱水反应，得到式（2）所代表的具有光学活性的 1-烷基-3-（保护氨基）吡咯烷-2,5-二酮化合物、随后从式（2）代表的化合物的 3 位氨基上消除保护基团，得到式（3）代表的光学活性 1-烷基-3-氨基吡咯烷-2,5-二酮化合物、用质子酸还原式（3）所代表化合物的羰基，以获得光学活性的 1-烷基-3-氨基吡咯烷化合物（式（4）所代表）或其盐，然后将式（4）所代表化合物或其盐进行氢解，以获得光学活性的 1H-3- 氨基吡咯烷或其质子酸盐。
• Process for producing optically active 1H-3-aminopyrrolidine and derivatives thereof
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1188744B1

  公开（公告）日：2005-11-02