1-Aza-adamant-4-methylen | 42949-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Aza-adamant-4-methylen
• 英文别名: 1-Azatricyclo(3.3.1.13,7)decane, 4-methylene-；4-methylidene-1-azatricyclo[3.3.1.13,7]decane
• CAS: 42949-22-4
• 化学式: C₁₀H₁₅N
• 分子量: 149.236
• InChiKey: NERALVJAYPYDQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Aza-adamant-4-methylen 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以83%的产率得到2-methylene-5-azadamantane N-oxide
  参考文献：
  名称：

  Face Selection in Additions to the Trigonal C2 Site in Quaternized 5-Azaadamantane Derivatives

  摘要：

  The quaternary N-allyl bromide salt 5 of allyl alpha-[2-(5-azaadamantylidene)]benzyl ether upon warming gave the Claisen rearrangement products 6 is the ratio E/Z = 93:7. The epoxidation of the N-oxide 8 of 2-methylene-5-azaadamantane 7 with m-CPBA gives rise to the two diastereomeric epoxides 9 in the ratio E/Z = 19:81. Reaction of the methyl iodide salt of this olefin with bromine in water produces the E- and Z-dibromides 10 in the ratio 74:26 as well as the corresponding glycols 12 in the ratio 86:14. The same reaction in methanol gives the E- and Z-isomers of 10 alone, in the ratio of 35:65. The interpretation is that, in all of these reactions, the trigonal carbon preferably undergoes addition at that face which is antiperiplanar to the more electron-rich vicinal bonds, and does so by margins substantially in excess of those observed with the corresponding 5-fluoroadamantanes. This fact lends further strength to our previously drawn conclusion that hyperconjugative transition state stabilization is the principal factor in the electronic component of face selection.

  DOI：

  10.1021/ja00151a005
• 作为产物：
  描述：

  5-氮杂金刚烷-2-酮 在 正丁基锂 、 三苯基膦氢溴酸盐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-Aza-adamant-4-methylen
  参考文献：
  名称：

  COMPOUNDS CONTAINING AN ALICYCLIE STRUCTURE AND ANTI-TUMOR APPLICATION

  摘要：

  这项发明涉及含有金刚烷基团或其类似物的新化合物的抗肿瘤活性。该发明还涉及利用这种含有金刚烷基团的S、P、T结构的化合物与立体异构体、互变异构体、前药、药用盐、复杂盐或溶剂化物的结合来治疗抗肿瘤和其他疾病的药物应用，这些抗肿瘤剂具有以下一般公式：

  公开号：

  US20140045779A1

文献信息

• [EN] AZAADAMANTANE DERIVATIVES AND METHODS OF USE<br/>[FR] DÉRIVÉS D'AZA-ADAMANTANE ET PROCÉDÉS D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2008058096A2

  公开（公告）日：2008-05-15

  (EN) The invention relates to compounds that are azaadamantane derivatives of formula (I), particularly ether- or amine -substituted azaadamantane derivatives and salts and prodrugs thereof, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.(FR) Cette invention concerne des composés qui sont des dérivés d'aza-adamantane, en particulier des dérivés d'aza-adamantane substitué par un éther ou une amine, ainsi que leurs sels et précurseurs, des compositions comprenant de tels composés, des procédés utilisant de tels composés et compositions, des procédés de préparation de tels composés et les intermédiaires obtenus au cours de tels procédés.
• COMPOUNDS CONTAINING AN ALICYCLIE STRUCTURE AND ANTI-TUMOR APPLICATION
  申请人：Xu Lifeng

  公开号：US20140045779A1

  公开（公告）日：2014-02-13

  This invention relates with anti-tumor activities of new compounds containing an adamantyl group or analogs thereof. The invention also relates with the medication applications of anti-tumor and other diseases by this kind of compounds with the combination of S, P, T structures containing adamantyl group and the formation of stereoisomer, tautomers, prodrug, pharmaceutically acceptable salts, complex salts or solvates to their anticancer application and anticancer agents, which have the following general formula:

  这项发明涉及含有金刚烷基团或其类似物的新化合物的抗肿瘤活性。该发明还涉及利用这种含有金刚烷基团的S、P、T结构的化合物与立体异构体、互变异构体、前药、药用盐、复杂盐或溶剂化物的结合来治疗抗肿瘤和其他疾病的药物应用，这些抗肿瘤剂具有以下一般公式：
• Face Selection in Additions to the Trigonal C2 Site in Quaternized 5-Azaadamantane Derivatives
  作者：Jacqueline Lau、Elena M. Gonikberg、Jui-te Hung、William J. le Noble

  DOI：10.1021/ja00151a005

  日期：1995.11

  The quaternary N-allyl bromide salt 5 of allyl alpha-[2-(5-azaadamantylidene)]benzyl ether upon warming gave the Claisen rearrangement products 6 is the ratio E/Z = 93:7. The epoxidation of the N-oxide 8 of 2-methylene-5-azaadamantane 7 with m-CPBA gives rise to the two diastereomeric epoxides 9 in the ratio E/Z = 19:81. Reaction of the methyl iodide salt of this olefin with bromine in water produces the E- and Z-dibromides 10 in the ratio 74:26 as well as the corresponding glycols 12 in the ratio 86:14. The same reaction in methanol gives the E- and Z-isomers of 10 alone, in the ratio of 35:65. The interpretation is that, in all of these reactions, the trigonal carbon preferably undergoes addition at that face which is antiperiplanar to the more electron-rich vicinal bonds, and does so by margins substantially in excess of those observed with the corresponding 5-fluoroadamantanes. This fact lends further strength to our previously drawn conclusion that hyperconjugative transition state stabilization is the principal factor in the electronic component of face selection.