1,3-二乙基金刚烷 | 25074-51-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 1,3-二乙基金刚烷
• 英文名称: 1,3-diethyladamantane
• CAS: 25074-51-5
• 化学式: C₁₄H₂₄
• 分子量: 192.345
• InChiKey: XHQDEOWLMBIVBU-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 10 Torr)
• 密度：
  0.942±0.06 g/cm3(Predicted)
• 保留指数：
  1377;1387;1377;1387

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-二乙基金刚烷 在 溴 作用下， 反应 4.0h， 生成 N-acetyl-3,5-diethyl-1-aminoadamantane
  参考文献：
  名称：

  Structure-anti-Parkinson activity relationships in the aminoadamantanes. Influence of bridgehead substitution

  摘要：

  A limited series of bridgehead alkyl-, dialkyl-, and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists. The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/alpha-methyltyrosine induced akinesia. Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series. While activities in both series increase with increasing liphophilicity, the methyl series (1b--d), as well as amantadine itself (1a), exhibit only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia. The ethyl series (1e,f) exhibits weak but reproducible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f. The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.

  DOI：

  10.1021/jm00343a010
• 作为产物：
  描述：

  1,3-金刚烷二乙酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 17.0h， 生成 1,3-二乙基金刚烷
  参考文献：
  名称：

  Structure-anti-Parkinson activity relationships in the aminoadamantanes. Influence of bridgehead substitution

  摘要：

  A limited series of bridgehead alkyl-, dialkyl-, and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists. The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/alpha-methyltyrosine induced akinesia. Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series. While activities in both series increase with increasing liphophilicity, the methyl series (1b--d), as well as amantadine itself (1a), exhibit only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia. The ethyl series (1e,f) exhibits weak but reproducible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f. The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.

  DOI：

  10.1021/jm00343a010

文献信息

• 一种新的金刚乙胺类似物及其合成方法
  申请人：无锡福祈制药有限公司

  公开号：CN109574856A

  公开（公告）日：2019-04-05

  本发明提供了本发明提供了一种新的金刚乙胺类似物，其结构如式(Ⅰ)所示：本发明所述揭示的金刚乙胺类似物，其活性更好，更有利于药物的临床使用和进一步开发研究。
• One pot synthesis of bridgehead amino alcohols from diamantoid hydrocarbons
  作者：Elena A. Ivleva、Maria S. Zaborskaya、Vadim A. Shiryaev、Yuri N. Klimochkin

  DOI：10.1080/00397911.2023.2177173

  日期：2023.3.19

  Abstract An efficient approach for the synthesis of amino alcohols directly from cage hydrocarbons has been developed. Multigram scalability, good yields and one-pot procedure, that utilize readily available reagents along with synthetic convenience showed its usefulness. The proposed one-pot method includes sequential reactions of cage hydrocarbon with nitric acid, further amination of intermediate

  摘要 已经开发出一种直接从笼形烃合成氨基醇的有效方法。多克可扩展性、良好的产量和一锅法，利用现成的试剂以及合成的便利性，显示了它的实用性。所提出的一锅法包括笼式烃与硝酸的连续反应，中间体硝基衍生物与尿素的进一步胺化，然后在添加浓溶液时将先前产生的胺氧化成氨基醇。H 2 SO 4。
• One-pot amination of cage hydrocarbons
  作者：M. V. Leonova、M. Yu. Skomorokhov、I. K. Moiseev、Yu. N. Klimochkin

  DOI：10.1134/s1070428015120064

  日期：2015.12

  A one-pot procedure has been proposed for the synthesis of amines directly from cage hydrocarbons. A number of cage amines have been synthesized by treatment of adamantane, its homologs, and structurally related cage hydrocarbons with nitric acid in acetic acid and subsequent addition of urea and heating.
• Alkylation of adamantane with alkyl halides catalyzed by ruthenium complexes
  作者：R. I. Khusnutdinov、N. A. Schchadneva、A. I. Malikov、U. M. Dzhemilev

  DOI：10.1134/s0965544106030030

  日期：2006.5

  The feasibility of catalytic alkylation of adamantane and 1-bromoadamantane with alkyl halides in the presence of ruthenium-containing catalysts was revealed. The optimum molar ratios between the catalyst components and the reactants, as well as the reaction conditions for the selective synthesis of mono- and dialkylsubstituted adamantane derivatives with a 70-98% yield, were determined.
• Stepanov,F.N. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 2123 - 2125
  作者：Stepanov,F.N. et al.

  DOI：——

  日期：——

表征谱图