(2S,4R)-2-(羧甲基)-4-羟基吡咯烷-1-羧酸叔丁酯 | 1034128-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S,4R)-2-(羧甲基)-4-羟基吡咯烷-1-羧酸叔丁酯
• 英文名称: N-BOC-L-(4-hydroxy)homoproline
• 英文别名: (2S,4R)-2-(carboxymethyl)-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester；2-[(2S,4R)-1-[(tert-butoxy)carbonyl]-4-hydroxypyrrolidin-2-yl]aceticacid；2-[(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetic acid
• CAS: 1034128-41-0
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: ODADLSCORSWAER-JGVFFNPUSA-N

物化性质

• 沸点：
  408.5±30.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  87.07
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-(羧甲基)-4-羟基吡咯烷-1-羧酸叔丁酯 在 N-甲基吗啉 、 碘代三甲硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-(4-Hydroxy-pyrrolidin-2-yl)-but-3-yn-2-one
  参考文献：
  名称：

  Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons

  摘要：

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

  DOI：

  10.1021/ja0609046
• 作为产物：
  描述：

  L-β-高羟脯氨酸盐酸盐 、 二碳酸二叔丁酯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (2S,4R)-2-(羧甲基)-4-羟基吡咯烷-1-羧酸叔丁酯
  参考文献：
  名称：

  β-Amino acid substitutions and structure-based CoMFA modeling of hepatitis C virus NS3 protease inhibitors

  摘要：

  In an effort to develop a new type of HCV NS3 peptidomimetic inhibitor, a series of tripeptide inhibitors incorporating a mix of alpha- and beta-amino acids has been synthesized. To understand the structural implications of beta-amino acid substitution, the P-1, P-2, and P-3 positions of a potent tripeptide scaffold were scanned and combined with carboxylic acid and acyl sulfonamide C-terminal groups. Inhibition was evaluated and revealed that the structural changes resulted in a loss in potency compared with the a- peptide analogues. However, several compounds exhibited mu M potency. Inhibition data were compared with modeled ligand-protein binding poses to understand how changes in ligand structure affected inhibition potency. The P-3 position seemed to be the least sensitive position for beta-amino acid substitution. Moreover, the importance of a proper oxyanion hole interaction for good potency was suggested by both inhibition data and molecular modeling. To gain further insight into the structural requirements for potent inhibitors, a three-dimensional quantitative structure-activity relationship (3D- QSAR) model has been constructed using comparative molecular field analysis (CoMFA). The most predictive CoMFA model has q(2) = 0.48 and r(pred)(2) = 0.68. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.005

文献信息

• Enantiospecific synthesis and cytotoxicity of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one enantiomers
  作者：F. Scott Kimball、Brandon J. Turunen、Keith C. Ellis、Richard H. Himes、Gunda I. Georg

  DOI：10.1016/j.bmc.2008.02.073

  日期：2008.4

  An enantiospecific synthesis was developed to generate both enantiomers of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one. A biological assay utilizing the HCT-116 colon cancer cell line to determine the cytotoxicity of these analogs revealed that only the (R)-enantiomer exhibited appreciable cytotoxicity with an IC(50) value of 0.2 microM.

  开发了一种对映特异性合成来生成 7-(4-甲氧基苯基)-6-苯基-2,3,8,8a-四氢吲哚嗪-5(1H)-one 的两种对映异构体。利用 HCT-116 结肠癌细胞系来确定这些类似物的细胞毒性的生物测定表明，只有 (R)-对映体表现出明显的细胞毒性，IC(50) 值为 0.2 microM。