3-(Benzenesulfonyl)bicyclo[1.1.0]butane-1-carboxylic acid | 124291-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(Benzenesulfonyl)bicyclo[1.1.0]butane-1-carboxylic acid
• CAS: 124291-40-3
• 化学式: C₁₁H₁₀O₄S
• 分子量: 238.264
• InChiKey: HPDYJHFTSDBNEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Benzenesulfonyl)bicyclo[1.1.0]butane-1-carboxylic acid 在 sodium azide 、 四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以92%的产率得到cis-1-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid
  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：

  4-(-phenylsulfonyl)-1,2-epoxybutane 在 正丁基锂 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 3-(Benzenesulfonyl)bicyclo[1.1.0]butane-1-carboxylic acid
  参考文献：
  名称：

  新的桥头取代的1-（芳基磺酰基）双环[1.1.0]丁烷和双环体系的一些新加成反应

  摘要：

  考虑到目标环丁烷衍生物的计划合成，从砜1–7制备了一系列新的3-取代的双环丁烷。然后将涉及中心键的一些新颖的加成反应应用于一些新化合物以及一些先前描述的双环丁烷。这些反应包括加入肼酸，除甲基试剂以外的氰基铜酸盐试剂和苯硒酚，以及添加苯硒基叠氮化物和溴化锂的单个例子。通过转化为环丁烷，环氧化和分子内碱诱导的环化反应，将几种3-烯丙基化的双环丁烷衍生物转化为1-（芳基磺酰基）双环[2.1.1]己烷。

  DOI：

  10.1016/s0040-4020(01)80112-5

文献信息

• Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives
  作者：Yehiel Gaoni、Astrid G. Chapman、Naila Parvez、Peter C.-K. Pook、David E. Jane、Jeffrey C. Watkins

  DOI：10.1021/jm00051a005

  日期：1994.12

  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.
• GAONI, YEHIEL, TETRAHEDRON, 45,(1989) N, C. 2819-2840
  作者：GAONI, YEHIEL

  DOI：——

  日期：——
• New bridgehead-substituted 1-(arylsulfonyl)bicyclo[1.1.0]butanes and some novel addition reactions of the bicyclic system
  作者：Yehiel Gaoni

  DOI：10.1016/s0040-4020(01)80112-5

  日期：1989.1

  In view of planned syntheses of target cyclobutane derivatives, a series of new 3-substituted bicyclobutanes was prepared from sulfones 1–7. Some novel addition reactions involving the central bond were then applied to several of the new compounds as well as to some previously described bicyclobutanes. These reactions include the additions of hydrazoic acid, of cyanocuprate reagents other than methyl

  考虑到目标环丁烷衍生物的计划合成，从砜1–7制备了一系列新的3-取代的双环丁烷。然后将涉及中心键的一些新颖的加成反应应用于一些新化合物以及一些先前描述的双环丁烷。这些反应包括加入肼酸，除甲基试剂以外的氰基铜酸盐试剂和苯硒酚，以及添加苯硒基叠氮化物和溴化锂的单个例子。通过转化为环丁烷，环氧化和分子内碱诱导的环化反应，将几种3-烯丙基化的双环丁烷衍生物转化为1-（芳基磺酰基）双环[2.1.1]己烷。
• Gaoni, Yehiel, Organic Preparations and Procedures International, 1995, vol. 27, # 2, p. 185 - 212
  作者：Gaoni, Yehiel

  DOI：——

  日期：——