hexahydro-2,5-methanopentalene-3a(1H)-carboxamide | 180406-64-8

• 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: hexahydro-2,5-methanopentalene-3a(1H)-carboxamide
• 英文别名: Tricyclo[3.3.1.03,7]nonane-3-carboxamide
• CAS: 180406-64-8
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: MSACEAXNZBOLMP-UHFFFAOYSA-N

物化性质

• 沸点：
  329.7±9.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  hexahydro-2,5-methanopentalene-3a(1H)-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 [(tricyclo[3.3.1.0(3,7)]non-3-yl)methyl]amine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs

  摘要：

  The synthesis of several (3-noradamantyl)amines, [(3-noradamantyl)methyl]amines, (3,7-dimethyl-1-bisnoradamantyl)amines, and [(3,7-dimethyl-1-bisnoradamantyl)methyl]amines is reported. They were evaluated against a wide range of viruses and one of them inhibited the cytopathicity of influenza A virus at a concentration similar to that of amantadine. Several of the new polycyclic amines show an interesting activity as NMDA receptor antagonists. A rimantadine analogue displayed significant trypanocidal activity. Moreover, to further characterize the pharmacology of these compounds, their effects on dopamine uptake were also assessed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.028
• 作为产物：
  描述：

  3-甲基碳酸胺 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 hexahydro-2,5-methanopentalene-3a(1H)-carboxamide
  参考文献：
  名称：

  2-(1-金刚烷基)金刚烷的生成和反应。重排为 3-(1-Adamantyl)-4-protoadamantylidene

  摘要：

  (1-金刚烷基)(3-去甲金刚烷基)甲基七氟丁酸酯在 100 °C 的 SN1 甲醇分解产生 (1-金刚烷基)(3-去甲金刚烷基) 甲基甲基醚 (17)、2-(1-金刚烷基)-1-甲氧基金刚烷 ( 18) 和 4-(1-金刚烷基)-3-甲氧基原金刚烷 (19) 的比例为 2:65:33。(1-金刚烷基)(3-去甲金刚烷基)重氮甲烷 (7) 在 0 °C 的甲醇分解也产生了比例为 4:33:63 的 17、18 和 19。另一方面，7 在 99 : 1 (v/v) 己烷-甲醇中的光解得到 17、18、2-(1-金刚烷基)-2-甲氧基金刚烷 (25) 和 2-(1-金刚烷基)- 2,4-二脱氢金刚烷 (20)，比例为 30:9:36:25。三乙胺的存在降低了醚 17、18 和 25 的产率，并将产率提高了 20% 至 46%。光解产物中大量 17 的形成和 19 的缺失表明生成了（1-金刚烷基

  DOI：

  10.1246/bcsj.69.2053

文献信息

• Cycloalkylamides and their therapeutic applications
  申请人：——

  公开号：US20040209858A1

  公开（公告）日：2004-10-21

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of a variety of disorders including, but not limited to, epilepsy, bipolar disorder, psychiatric disorders, migraine, pain, neuroprotection, and movement disorders.

  本发明涉及使用式(I)1的化合物治疗多种疾病，包括但不限于癫痫、双相情感障碍、精神障碍、偏头痛、疼痛、神经保护和运动障碍。
• Carbon Tunneling in the Ring Expansion of Noradamantylchlorocarbene
  作者：Robert A. Moss、Ronald R. Sauers、Robert S. Sheridan、Jingzhi Tian、Peter S. Zuev

  DOI：10.1021/ja0488939

  日期：2004.8.1

  in solution with laser flash photolysis via its pyridinium ylide, and in N2 or Ar matrixes at 9 K with IR and UV/vis spectroscopy. At ambient temperatures, or on irradiation in the cryogenic matrixes, the carbene rearranged to 2-chloro-1-adamantene, which could be trapped in solution and which was characterized by IR and UV/vis at low temperatures. In the dark at 9 K, the carbene also slowly ring-expanded

  辐照 3-(3-noradamantyl)-3-chlorodiazirine 产生相应的去甲金刚烷基氯卡宾，可通过其吡啶鎓叶立德在溶液中用激光闪光光解检测到，在 N2 或 Ar 基质中在 9 K 下用红外和紫外/可见光谱检测。在环境温度下，或在低温基质中照射时，卡宾重排为 2-氯-1-金刚烷，其可以被困在溶液中，并在低温下通过 IR 和 UV/vis 进行表征。在 9 K 的黑暗中，卡宾也以大约 10 的速率缓慢环膨胀为氯金刚烷。比其 B3LYP 计算的激活屏障预测的快 10111 倍。提出低温重排是通过碳量子力学隧穿发生的。
• Proteasome inhibitors and methods of using the same
  申请人：Bernadini Raffaella

  公开号：US20050107307A1

  公开（公告）日：2005-05-19

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以通过抑制蛋白酶体活性等方式调节细胞凋亡。这些化合物和组合物可以用于诱导细胞凋亡并治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。
• PROTEASOME INHIBITORS AND METHODS OF USING THE SAME
  申请人：Bernardini Raffaella

  公开号：US20090291918A1

  公开（公告）日：2009-11-26

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可以用于诱导细胞凋亡和治疗癌症及其他与蛋白酶体活性直接或间接相关的疾病。
• Proteasome Inhibitors and Methods of Using the Same
  申请人：Bernardini Raffaella

  公开号：US20110144033A1

  公开（公告）日：2011-06-16

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可用于诱导细胞凋亡和治疗癌症和其他与蛋白酶体活性直接或间接相关的疾病的方法。