(±)-methyl 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylate | 1169936-04-2

• 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: (±)-methyl 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylate
• 英文别名: 1-Cyclopentene-1-carboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester；methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentene-1-carboxylate
• CAS: 1169936-04-2
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: BPVUUOLKMLXVJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-methyl 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylate 在 三乙胺 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.25h， 生成 (±)-tert-butyl (3-(methoxycarbamoyl)cyclopent-3-en-1-yl)carbamate
  参考文献：
  名称：

  γ-Aminobutyric Acid(C) (GABA_C) Selective Antagonists Derived from the Bioisosteric Modification of 4-Aminocyclopent-1-enecarboxylic Acid: Amides and Hydroxamates

  摘要：

  Series of compounds were generated via the bioisosteric replacement of the carboxylate of 4-ACPCA (2) with hydroxamate or amide groups. All compounds from this study exhibited increased selectivity for GABA(C), the most potent being 4-ACPHA (10a, IC50 = 13 mu M) and 4-ACPAM (11a, IC50 = 10 mu M). This provides evidence that a zwitterionic structure is not essential for GABA(C) antagonists, rather the emphasis lies in appropriate heteroatoms to participate in hydrogen bonding.

  DOI：

  10.1021/jm4006548
• 作为产物：
  描述：

  methyl 4-tert-butoxycarbonylamino-2-cyclopenten-1-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 (±)-methyl 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylate
  参考文献：
  名称：

  γ-Aminobutyric Acid(C) (GABA_C) Selective Antagonists Derived from the Bioisosteric Modification of 4-Aminocyclopent-1-enecarboxylic Acid: Amides and Hydroxamates

  摘要：

  Series of compounds were generated via the bioisosteric replacement of the carboxylate of 4-ACPCA (2) with hydroxamate or amide groups. All compounds from this study exhibited increased selectivity for GABA(C), the most potent being 4-ACPHA (10a, IC50 = 13 mu M) and 4-ACPAM (11a, IC50 = 10 mu M). This provides evidence that a zwitterionic structure is not essential for GABA(C) antagonists, rather the emphasis lies in appropriate heteroatoms to participate in hydrogen bonding.

  DOI：

  10.1021/jm4006548

文献信息

• [EN] SUBSTITUTED CYCLOPENTENES, THEIR PREPARATION AND THEIR USE FOR CHIRAL SCAFFOLDS<br/>[FR] CYCLOPENTENES SUBSTITUES, LEUR PREPARATION ET LEUR UTILISATION POUR DES OSSATURES CHIRALES
  申请人：CHIROTECH TECHNOLOGY LTD

  公开号：WO2001017952A1

  公开（公告）日：2001-03-15

  3,4-Disubstituted-1-cyclopentene compounds, in substantially enantiopure form, have the relative stereochemistry according to formula (1A) or (1B) including the opposite enantiomers thereof, wherein R1 is either COOX, wherein X is alkyl, H or a salt-forming cation, or CH¿2?OH, wherein the hydroxyl group is optionally protected; R?2¿ is H or a protecting group; R3 is H or alkyl; and R4 is H, alkoxy, alkyl, aryl or aralkyl; or, in the case of formula 1A, R?2 and R4¿ are linked to form an oxazolidinone ring. These compounds can be used to prepare a series of complementary stereochemically varied cyclopentane scaffolds.

  3,4-二取代-1-环戊烯化合物，其绝大部分为对映体纯形式，具有相对立体化学式(1A)或(1B)，包括其相反对映体，其中R1为COOX，其中X为烷基，氢或形成盐的阳离子，或CH2OH，其中羟基可选地被保护；R2为氢或保护基；R3为氢或烷基；R4为氢，烷氧基，烷基，芳基或芳基烷基；或者，在公式1A的情况下，R2和R4结合形成噁唑烷酮环。这些化合物可用于制备一系列互补的立体化学变化的环戊烷支架。
• SUBSTITUTED CYCLOPENTENES, THEIR PREPARATION AND THEIR USE FOR CHIRAL SCAFFOLDS
  申请人：Chirotech Technology Limited

  公开号：EP1210324A1

  公开（公告）日：2002-06-05
• γ-Aminobutyric Acid(C) (GABA_C) Selective Antagonists Derived from the Bioisosteric Modification of 4-Aminocyclopent-1-enecarboxylic Acid: Amides and Hydroxamates
  作者：Katherine E. S. Locock、Izumi Yamamoto、Priscilla Tran、Jane R. Hanrahan、Mary Chebib、Graham A. R. Johnston、Robin D. Allan

  DOI：10.1021/jm4006548

  日期：2013.7.11

  Series of compounds were generated via the bioisosteric replacement of the carboxylate of 4-ACPCA (2) with hydroxamate or amide groups. All compounds from this study exhibited increased selectivity for GABA(C), the most potent being 4-ACPHA (10a, IC50 = 13 mu M) and 4-ACPAM (11a, IC50 = 10 mu M). This provides evidence that a zwitterionic structure is not essential for GABA(C) antagonists, rather the emphasis lies in appropriate heteroatoms to participate in hydrogen bonding.