(1S,2R)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid | 213688-27-8

• 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: (1S,2R)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid
• CAS: 213688-27-8
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: NCZNLCOWPUFGKA-HQJQHLMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid 在 吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 三氟甲磺酸酐 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 柠檬酸 、 sodium nitrite 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成 (2aR,4aS,6aR,6bS)-4-(4-Methoxy-benzyl)-3-oxo-3,4,5,6,6a,6b-hexahydro-2aH-1,2,4-triaza-cyclopenta[cd]pentalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

  摘要：

  Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17) via an intramolecular cyclopropanation of alpha-diazo acetamide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01316-9
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-氨基-2-羟基环戊烷羧酸 在 四甲基氢氧化铵 作用下， 以 乙腈 为溶剂， 反应 144.0h， 生成 (1S,2R)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid
  参考文献：
  名称：

  Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

  摘要：

  Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17) via an intramolecular cyclopropanation of alpha-diazo acetamide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01316-9

文献信息

• Syntheses of potent Leu-enkephalin analogs possessing β-hydroxy-α,α-disubstituted-α-amino acid and their characterization to opioid receptors
  作者：Manabu Horikawa、Yasushi Shigeri、Noboru Yumoto、Susumu Yoshikawa、Terumi Nakajima、Yasufumi Ohfune

  DOI：10.1016/s0960-894x(98)00349-7

  日期：1998.8

  Novel Leu-enkephalin (Leu-Enk) (1) analogs possessing various types of a-substituted serine instead of its glycine residue in the position 2 were synthesized via an efficient O,N-migration method. The binding characteristics of the synthetic analogs using Chinese hamster ovary (CHO) cells expressed cloned rat mu-, delta-, and kappa-receptors revealed that [(1R,2S)-Ahh(2)]Enk (7) was the most potent agonist of delta-opioid receptors among all the synthetic analogs tested, and was 10 times more potent than the native Leu-Enk. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Imaging Agents
  申请人：EMORY UNIVERSITY

  公开号：US20130123618A1

  公开（公告）日：2013-05-16

  This invention provides amino acid derivatives useful in detecting and evaluating brain and body tumors, including (1S,2S) anti-2-[ 18 F]FACPC and (1R,2R) anti-2-[ 18 F]FACPC.