cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide | 117488-02-5

• 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: cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide
• 英文别名: cis-1-azido-3-(phenylsulfonyl)cyclobutane-1-N,N-pentamethylenecarboxamide
• CAS: 117488-02-5
• 化学式: C₁₆H₂₀N₄O₃S
• 分子量: 348.426
• InChiKey: BEZFNVXBQHKHHL-FZNQNYSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide 在 palladium on activated charcoal 盐酸 、 sodium amalgam 、 正丁基锂 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， -50.0~130.0 ℃ 、101.33 kPa 条件下， 反应 49.0h， 生成 cis-ACBD,cis-1-Aminocyclobutane-1,3-dicarboxylicacid
  参考文献：
  名称：

  Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives

  摘要：

  A range of cis- and trans-3-substituted 1-aminocyclobutane-1-carboxylic acids has been synthesized and evaluated for antagonism at excitatory amino acid receptor sites and for anticonvulsant activity. Potent and selective antagonist:activity at N-methyl-D-aspartate (NMDA) receptor sites in neonatal rat motoneurones was shown by compounds in which the 3-substituent was, or contained, a 2'-carboxyethyl or 2'-phosphonoethyl moiety. Substances 4b, 24, 35, and 40 were more potent than the standard NMDA receptor antagonist, D-2-amino-5-phosphonopentanoate (D-AP5) as NMDA antagonists in this preparation, and about equipotent with [3-(+/-)-2-carboxypiperazin-4-yl)-1-propyl]phosphonate (CPP). Anticonvulsant activity, as assessed following intracerebroventricular injection into audiogenic DBA/2 mice, generally paralleled NMDA receptor antagonist activity.

  DOI：

  10.1021/jm00051a005
• 作为产物：
  描述：

  3-(Benzenesulfonyl)bicyclo[1.1.0]butane-1-carboxylic acid 在 氯化亚砜 、 sodium azide 、 四甲基胍 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 cis-1-Azido-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide
  参考文献：
  名称：

  Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives

  摘要：

  A range of cis- and trans-3-substituted 1-aminocyclobutane-1-carboxylic acids has been synthesized and evaluated for antagonism at excitatory amino acid receptor sites and for anticonvulsant activity. Potent and selective antagonist:activity at N-methyl-D-aspartate (NMDA) receptor sites in neonatal rat motoneurones was shown by compounds in which the 3-substituent was, or contained, a 2'-carboxyethyl or 2'-phosphonoethyl moiety. Substances 4b, 24, 35, and 40 were more potent than the standard NMDA receptor antagonist, D-2-amino-5-phosphonopentanoate (D-AP5) as NMDA antagonists in this preparation, and about equipotent with [3-(+/-)-2-carboxypiperazin-4-yl)-1-propyl]phosphonate (CPP). Anticonvulsant activity, as assessed following intracerebroventricular injection into audiogenic DBA/2 mice, generally paralleled NMDA receptor antagonist activity.

  DOI：

  10.1021/jm00051a005

文献信息

• Regiospecific additions of hydrazoic acid and benzylamine to 1-(arylsulfonyl)bicyclo[1.1.0]Butanes. Application to the synthesis of cis and trans 2,7-methanoglutamic acids
  作者：Yehiel Gaoni

  DOI：10.1016/s0040-4039(00)80361-5

  日期：——

  Addition of hydrazoic acid or benzylamine to 1-(arylsulfonyl) bicyclobutanes introduces the nitrogen nucleophlle at position 3 of the derived cyclobutane, even when a carboxyl derivative is present at this position as a second activating group. Precursors of α-amino cyclobutane carboxylic acids may thus be obtained and these can be further transformed to the title diacids via carbonylation α to the

  即使将羧基衍生物作为第二活化基团存在于该位置的环丁烷的3位上，向1（芳基磺酰基）双环丁烷中添加氢唑酸或苄基胺也可在该位置上引入氮原子。因此可以得到α-氨基环丁烷羧酸的前体，并且可以通过将α羰基化成砜并还原，将它们进一步转化为标题二酸。
• Gaoni, Yehiel, Organic Preparations and Procedures International, 1995, vol. 27, # 2, p. 185 - 212
  作者：Gaoni, Yehiel

  DOI：——

  日期：——
• Stable Monosubstituted Triazenes by Reduction of Some Tertiary Azides
  作者：Yehiel Gaoni

  DOI：10.1021/jo00101a057

  日期：1994.11