N-benzyloxycarbonyl-5-oxo-(S)-pipecolic acid | 117836-14-3

• 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-benzyloxycarbonyl-5-oxo-(S)-pipecolic acid
• 英文别名: (2S)-5-Oxo-1,2-piperidinedicarboxylic acid 1-benzyl ester；(2S)-5-oxo-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid
• CAS: 117836-14-3
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: IBZDRDHRFDYPTQ-LBPRGKRZSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  1.355

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到N-benzyloxycarbonyl-5-oxo-(S)-pipecolic acid
  参考文献：
  名称：

  Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline

  摘要：

  An efficient diastereo selective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydrOXY-L-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.035

文献信息

• Carboxyalkyl dipeptides
  申请人：Schering Corporation

  公开号：US05348944A1

  公开（公告）日：1994-09-20

  Compounds of the formula ##STR1## useful as antihypertensive agents are disclosed.

  公开了化学式为##STR1##的化合物，其作为降压剂具有用途。
• Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them
  申请人：SCHERING CORPORATION

  公开号：EP0050800A1

  公开（公告）日：1982-05-05

  Disclosed are novel carboxyalkyl dipeptides which are useful as inhibitors of angiotensinconverting enzyme and as antihypertensive agents, having the formula and the pharmaceutically acceptable salts thereof, wherein R and R6 are for example hydroxy, lower alkoxy or arylloweralkoxy; R' is for example hydrogen, alkyl, lower alkoxy or aryloxy; R2 and R are the same or different and are hydrogen or lower alkyl; R3 is for example lower alkyl or phenyl lower alkyl; R4 and R5 are selected from hydrogen, lower alkyl and Z, or R4 and R5 taken together form a group represented by Q, U, V, Y, D or E wherein wherein X' and X2 independent of each other are 0, S or CH2, R8 and R9 independent of each other are lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl having 3 to 8 carbon atoms, hydroxy lower alkyl or -(CH2)nAr, wherein n is 0, 1, 2 or 3 or R8 and R9 taken together form a bridge W, wherein W is a single bond or a methylene bridge or a substituted methylene bridge when at least one of X' and X2 is methylene, or W is an alkylene or substituted alkylene bridge having 2 or 3 carbon atoms; with the proviso that at least one of R4 and R5 is Z; wherein L is O or S. The compounds can be prepared according to known methods such as for example by condensation of an aminoacid XXI with an aminoacid XVII wherein X1, X2 and W are as defined above; wherein G is oxygen, sulfur or CH2;

  本发明公开了可用作血管紧张素转换酶抑制剂和降压药的新型羧烷基二肽，其化学式为 其中 R 和 R6 例如是羟基、低级烷氧基或芳基低级烷氧基；R'例如是氢、烷基、低级烷氧基或芳基氧基；R2 和 R 相同或不同，并且是氢或低级烷基；R3 例如是低级烷基或苯基低级烷基；R4 和 R5 选自氢、低级烷基和 Z，或 R4 和 R5 共同形成由 Q、U、V、Y、D 或 E 代表的基团，其中 其中 X' 和 X2 互不相关，分别为 0、S 或 CH2，R8 和 R9 互不相关，分别为低级烷基、低级烯基、低级炔基、具有 3 至 8 个碳原子的环烷基、羟基低级烷基或-(CH2)nAr，其中 n 为 0、1、其中 W 是单键或亚甲基桥或取代的亚甲基桥（当 X' 和 X2 中至少有一个是亚甲基时），或 W 是具有 2 或 3 个碳原子的亚烷基或取代的亚烷基桥；但 R4 和 R5 中至少有一个是 Z； 这些化合物可根据已知方法制备，例如通过氨基酸 XXI 与氨基酸 XVII 缩合 其中 X1、X2 和 W 如上定义； 其中 G 为氧、硫或 CH2；
• US5348944A
  申请人：——

  公开号：US5348944A

  公开（公告）日：1994-09-20
• Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline
  作者：Jae-Chul Jung、Mitchell A. Avery

  DOI：10.1016/j.tetasy.2006.07.035

  日期：2006.10

  An efficient diastereo selective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydrOXY-L-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield. (c) 2006 Elsevier Ltd. All rights reserved.