1,3-bis[(2-tosyloxyethyloxy)methyl]adamantane | 80121-66-0

• 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: 1,3-bis[(2-tosyloxyethyloxy)methyl]adamantane
• 英文别名: Rel-(1s,3s,5r,7r)-adamantane-1,3-diylbis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate)；2-[3-[2-(4-methylphenyl)sulfonyloxyethyl]-1-adamantyl]ethyl 4-methylbenzenesulfonate
• CAS: 80121-66-0
• 化学式: C₂₈H₃₆O₆S₂
• 分子量: 532.722
• InChiKey: FQMILMSASTXIRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-bis[(2-tosyloxyethyloxy)methyl]adamantane 在 LiEt₃B 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以89.5%的产率得到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
• 作为产物：
  描述：

  1,3-金刚烷二乙酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 1,3-bis[(2-tosyloxyethyloxy)methyl]adamantane
  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

• Synthesis and alkali metal complexation studies of novel cage-functionalized cryptands
  作者：Tatjana Šumanovac Ramljak、Ines Despotović、Branimir Bertoša、Kata Mlinarić-Majerski

  DOI：10.1016/j.tet.2013.10.039

  日期：2013.12

  all cations, but showed practically no selectivity towards any of the alkali metal cation. The experimental findings are corroborated by calculation studies consisting of force field based conformational search using Monte Carlo method followed by investigation of the stabilities of the complexes of cryptands with Na+ and K+ metal ions in chloroform by means of quantum chemical calculations at the density

  新颖笼官能穴状配体的合成1 - 5含有金刚烷，2- oxaadamantane-或降金刚烷基的部分[即，1,3- diethyladamantano [2.2.0]穴状配体（1），1,3- diethoxyadamantano [2.2.2 ] cryptand（2），1,3-二[（（乙氧基）甲基]金刚烷[2.2.2] -cryptand（3），1,3-二[（（乙氧基）甲基] -2-氧杂金刚烷[2.2.3] cryptand （4）和1，2-二乙氧基正十二烷[2.2.2] cryptand（5）]和它们的碱金属结合性能得到了报道。通过提取实验获得的结果表明，所有的配体都显示出比母体[2.2.2]配体低的提取能力。但是，密码子1和2与参考[2.2.2] cryptand相比，对K +的选择性更高。当第三桥被两个额外的CH 2基团以及两个氧原子扩大时，如在配体3和4中，较大阳离子（K +，Rb
• Synthesis and alkali metal picrate extraction capabilities of a 4-oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-derived cryptand. A new ionophore for selective ion complexation
  作者：Alan P. Marchand、Sulejman Alihodžić、Artie S. McKim、Kaipenchery A. Kumar、Kata Mlinarić-Majerski、Tatjana Šumanovae、Simon G. Bott

  DOI：10.1016/s0040-4039(98)00120-8

  日期：1998.4

  The synthesis of a novel cage-functionalized cryptand, 5, and the X-ray crystal structure of its 1:1 complex with Na+, i.e. 4, are reported. Host molecule 5 displays high avidity toward Na+ and K+ picrates and appears to extract these cations selectively. The X-ray crystal structure of 4 clearly indicates that Na+ is bonded to all seven Lewis base centers (i.e., nitrogen and oxygen atoms) in the complex

  据报道合成了一种新型的笼功能化的穴状配体5及其与Na +即4形成1：1配合物的X射线晶体结构。宿主分子5对Na +和K +苦味酸盐显示出很高的亲和力，并且似乎选择性地提取了这些阳离子。X射线晶体结构4清楚地表明，Na +与络合物中所有七个路易斯碱中心（即氮和氧原子）键合。此外，获得了10的相应的碱金属苦味酸盐提取曲线，5的含金刚烷的类似物。除了可能提取K +苦味精的能力外，宿主分子10的碱金属苦味酸盐的提取能力与相应的单环模型系统（即N，N'-二乙基-4,13）之间的差异似乎很小。-diaza-18-crown-6（6）。
• HENKEL, J. G.;HANE, J. T.;GIANUTSOS, G., J. MED. CHEM., 1982, 25, N 1, 51-56
  作者：HENKEL, J. G.、HANE, J. T.、GIANUTSOS, G.

  DOI：——

  日期：——