4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester | 158469-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester
• 英文别名: Tert-butyl 4-(2-hydroxyacetyl)piperidine-1-carboxylate
• CAS: 158469-70-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: KJEHYFIHBRGGFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 4-<(2-hydroxy-1-methylene)ethyl>-1-piperidinecarboxylic acid(1,1-dimethylethyl) ester
  参考文献：
  名称：

  Boes, Michael; Canesso, Rolf, Heterocycles, 1994, vol. 38, # 8, p. 1889 - 1896

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 4-hydroxyacetylpiperidine hydrochloride 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以97%的产率得到4-(2-hydroxy-1-oxoethyl)-1-piperidinecarboxylic acid (1,1-dimethylethyl)ester
  参考文献：
  名称：

  Boes, Michael; Canesso, Rolf, Heterocycles, 1994, vol. 38, # 8, p. 1889 - 1896

  摘要：

  DOI：

文献信息

• Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists
  作者：Kenjiro Sato、Hiromichi Sugimoto、Kentaro Rikimaru、Hiroshi Imoto、Masahiro Kamaura、Nobuyuki Negoro、Yoshiyuki Tsujihata、Hirohisa Miyashita、Tomoyuki Odani、Toshiki Murata

  DOI：10.1016/j.bmc.2014.01.028

  日期：2014.3

  GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl) indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl] propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-(1-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2,3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration. (C) 2014 Elsevier Ltd. All rights reserved.
• Boes Michael, Canesso Rolf, Heterocycles, 38 (1994) N 8, S 1889-1896
  作者：Boes Michael, Canesso Rolf

  DOI：——

  日期：——