1-hydroxy-3-phenyl-2-oxaadamantane | 6465-36-7

• 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-hydroxy-3-phenyl-2-oxaadamantane
• 英文别名: 3-Hydroxy-1-phenyl-2-oxa-adamantan；3-Phenyl-2-oxatricyclo[3.3.1.1~3,7~]decan-1-ol；3-phenyl-2-oxatricyclo[3.3.1.13,7]decan-1-ol
• CAS: 6465-36-7
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: VRJFTTHRZSZJFI-UHFFFAOYSA-N

物化性质

• 熔点：
  148.5 °C
• 沸点：
  366.0±25.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-phenyl-2-oxaadamantane 在 盐酸 、 hydrazine hydrate 、 hydrochloric acid diethyl ether 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 18.0h， 以62%的产率得到(3-phenyl-2-oxaadamant-1-yl)hydrazine hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

  摘要：

  The synthesis of several (2-oxaadamant-1-yl) amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.007
• 作为产物：
  描述：

  二环[3.3.1]壬-3,7-二酮 、 苯基锂 以 四氢呋喃 为溶剂， 反应 6.5h， 以78%的产率得到1-hydroxy-3-phenyl-2-oxaadamantane
  参考文献：
  名称：

  Synthesis of 2-oxaadamantane and 1-aryl-2-oxaadamantanes

  摘要：

  The direct reduction of 1-hydroxy-2-oxaadamantanes derivatives to give 2-oxaadamantanes was unsuccessful. 2-Oxaadamantanes could, however, be prepared from 1-hydroxy-2-oxaadamantes by a ring opening reaction followed by reduction and subsequent ring-closure. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.027

文献信息

• Easy synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones by silica gel-promoted fragmentation of 3-alkyl-2-oxaadamant-1-yl mesylates
  作者：Pelayo Camps、Rachid El Achab、Merce` Font-Bardia、Diana Go¨rbig、Jordi Morral、Diego Mun˜oz-Torrero、Xavier Solans、Montserrat Simon

  DOI：10.1016/0040-4020(96)00217-7

  日期：1996.4

  A synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones4b-f and 4j, k by reaction of the corresponding 3-alkyl-2-oxaadamant-1-yl mesylates3 with silica gel in methylene chloride at room temperature, is described. The method failed to give enones4a, g and the related compounds4l, m, what can be rationalized on mechanistic grounds.

  通过使相应的3-烷基-2-氧杂芳基-1-基甲磺酸基酯3与硅胶在亚甲基中的反应，合成7-烷基双环[3.3.1] non-6-en-3-ones 4b-f和4j，k描述了室温下的氯化物。该方法未能给出烯酮4a，g和相关化合物4l，m，可以根据机械原理对其进行合理化。