2-adamantyl(phenyl)methanol | 53140-72-0

• 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: 2-adamantyl(phenyl)methanol
• CAS: 53140-72-0
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: QMWAFHSBQFIHPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-adamantyl(phenyl)methanol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2-Adamantyl phenyl ketone
  参考文献：
  名称：

  Enhanced Enantio- and Diastereoselectivity via Confinement and Cation Binding:  Yang Photocyclization of 2-Benzoyladamantane Derivatives within Zeolites

  摘要：

  Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a gamma-hydrogen abstraction process. The cyclobutanols readily undergo retro-aldol reaction to give delta-ketoesters. The enantiomeric excess (ee) in the endo-cyclobutanols is measured by monitoring the ee in the ketoesters. Whereas in solution the ee in the product ketoester is zero, within achiral NaY zeolite, in the presence of a chiral inductor such as pseudoephedrine, ee's up to 28% have been obtained. The influence of zeolite on several chiral esters of 2-benzoyladamantane-2-carboxylic acids has also been examined. Whereas in solution the diastereomeric excess is <15%, in zeolite the delta-ketoesters are obtained in 79% de (best examples). Ab initio computations suggest that enhancement of chiral induction within zeolites is likely to be due to cation complexation with the reactant ketone. Alkali ion-organic interaction, a powerful tool, is waiting to be fully exploited in photochemical and thermal reactions. In this context zeolites could be a useful medium as one could view them as a reservoir of "naked" alkali ions that are only partially coordinated to the zeolite walls.

  DOI：

  10.1021/jo0260793
• 作为产物：
  描述：

  2-methoxymethylene adamantane 在 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 2-adamantyl(phenyl)methanol
  参考文献：
  名称：

  Enhanced Enantio- and Diastereoselectivity via Confinement and Cation Binding:  Yang Photocyclization of 2-Benzoyladamantane Derivatives within Zeolites

  摘要：

  Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a gamma-hydrogen abstraction process. The cyclobutanols readily undergo retro-aldol reaction to give delta-ketoesters. The enantiomeric excess (ee) in the endo-cyclobutanols is measured by monitoring the ee in the ketoesters. Whereas in solution the ee in the product ketoester is zero, within achiral NaY zeolite, in the presence of a chiral inductor such as pseudoephedrine, ee's up to 28% have been obtained. The influence of zeolite on several chiral esters of 2-benzoyladamantane-2-carboxylic acids has also been examined. Whereas in solution the diastereomeric excess is <15%, in zeolite the delta-ketoesters are obtained in 79% de (best examples). Ab initio computations suggest that enhancement of chiral induction within zeolites is likely to be due to cation complexation with the reactant ketone. Alkali ion-organic interaction, a powerful tool, is waiting to be fully exploited in photochemical and thermal reactions. In this context zeolites could be a useful medium as one could view them as a reservoir of "naked" alkali ions that are only partially coordinated to the zeolite walls.

  DOI：

  10.1021/jo0260793

文献信息

• Facial selectivity in the addition of nucleophiles to the radical cations of substituted 2-methyleneadamantanes
  作者：Susan Swansburg、Kristin Janz、Gloria Jocys、Alexandra Pincock、James Pincock

  DOI：10.1139/v97-201

  日期：1998.1.1

  radical cation of each was generated by photochemical oxidation using 1,4-dicyanobenzene as the sensitizer, and their reactivity was examined in methanol-acetonitrile mixtures with added tetraethylammonium cyanide. Although compound 2 reacted only by tautomerization, the other compounds all gave addition products. For the monoaryl alkenes 3, 4, and 5, comparable yields of both methanol and HCN addition

  已经制备了二苯基亚甲基环己烷 2 和取代的 2-亚甲基金刚烷 3-7。每种自由基阳离子都是通过光化学氧化产生的，使用 1,4-二氰基苯作为敏化剂，并在添加了四乙基氰化铵的甲醇-乙腈混合物中检测它们的反应性。尽管化合物 2 仅通过互变异构反应，但其他化合物均产生加成产物。对于单芳基烯烃 3、4 和 5，甲醇和 HCN 加成产物的产率相当，这是由于烯烃自由基阳离子两端的亲核攻击所致。对于二苯基烯烃 6 和 7，区域选择性有利于对金刚烷基碳进行亲核攻击，并且加成产物主要是 HCN 加成的产物。对于 5-甲氧基化合物 7，
• Photoinduced B–Cl Bond Fission in Aldehyde-BCl₃ Complexes as a Mechanistic Scenario for C–H Bond Activation
  作者：Daniel P. Schwinger、Martin T. Peschel、Thomas Rigotti、Piotr Kabaciński、Thomas Knoll、Erling Thyrhaug、Giulio Cerullo、Jürgen Hauer、Regina de Vivie-Riedle、Thorsten Bach

  DOI：10.1021/jacs.2c06683

  日期：2022.10.19

  hydrocarbons undergo addition to the C═O double bond via a radical pathway. The photogenerated chlorine radical abstracts a hydrogen atom from the alkane, and the resulting carbon-centered radical either recombines with the borylated ketyl radical or adds to the ground-state aldehyde-BCl3 complex, releasing a chlorine atom. The existence of a radical chain was corroborated by quantum yield measurements and

  与羰基化合物一致，路易斯酸已被确定为一类多功能的光催化剂。迄今为止，研究主要集中在通过改变其光物理性质或通过修改其光化学来激活底物。在这项工作中，我们通过证明路易斯酸碱复合物的紫外光激发可导致路易斯酸中共价键的均裂裂解来扩展已建立的作用模式。在对苯甲醛和路易斯酸 BCl 3的络合物的研究中，我们发现了均裂 B-Cl 键断裂的证据，导致在激发后仅数百飞秒形成硼化的羰基自由基和游离氯原子。随时间变化的密度泛函理论和瞬态吸收实验都确定了苯甲醛-BCl 2阳离子作为在纳秒时间尺度上形成的主要物种。经实验验证的 B-Cl 键均裂被综合用于 BCl 3介导的芳香醛加氢烷基化反应（19 个例子，42-76% 产率）。发现碳氢化合物通过自由基途径加成到 C=O 双键。光生氯自由基从烷烃中夺取一个氢原子，由此产生的以碳为中心的自由基要么与硼化的羰基重新结合，要么加到基态醛-BCl 3上络合物，释放出一个氯原
• ADAMANTYLMETHYLAMINE DERIVATIVE AND USE THEREOF AS PHARMACEUTICAL
  申请人：Tohoku University

  公开号：EP3663279A1

  公开（公告）日：2020-06-10

  The present invention provides a pharmaceutical composition for treating or preventing a cognitive disease or disorder, comprising a compound represented by Formula (I), an enantiomer thereof, a diastereomer thereof, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种用于治疗或预防认知疾病或障碍的药物组合物，该组合物由式（I）代表的化合物、其对映体、非对映体或其药学上可接受的盐组成。
• EP3663279
  申请人：——

  公开号：——

  公开（公告）日：——
• Keul,H., Chemische Berichte, 1975, vol. 108, p. 1198 - 1206
  作者：Keul,H.

  DOI：——

  日期：——