1-bromo-3-phenyladamantane | 21816-07-9

• 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-bromo-3-phenyladamantane
• 英文别名: 1-Brom-3-phenyl-adamantan；1-Bromo-3-phenyl Adamantane
• CAS: 21816-07-9
• 化学式: C₁₆H₁₉Br
• 分子量: 291.231
• InChiKey: YQMDWXLAPBTRCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  353.7±21.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 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-bromo-3-phenyladamantane 在 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 14.0h， 生成 (2S)-1-(4-methylpiperidin-1-yl)-3-[4-(3-phenyladamantan-1-yl)phenoxy]propan-2-ol
  参考文献：
  名称：

  ADAMANTANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTION

  摘要：

  结构式I的化合物被开发用于治疗埃博拉病毒和马尔堡病毒等丝状病毒感染，其中，R1、R2、R3、X和Y在说明书中有定义。

  公开号：

  US20200017514A1
• 作为产物：
  描述：

  1-苯基金刚烷 在 氢溴酸 、 溶剂黄146 作用下， 生成 1-bromo-3-phenyladamantane
  参考文献：
  名称：

  叠合成1,3-二取代金刚烷胺

  摘要：

  1,3-二取代金刚烷的合成。

  DOI：

  10.1002/hlca.19760590609

文献信息

• Adamantane derivatives in the prevention and treatment of cerebral
  申请人：Merz + Co. GmbH & Co.

  公开号：US05061703A1

  公开（公告）日：1991-10-29

  A method for the prevention and treatment of cerebral ischemia using an adamantane derivative of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical or different, representing hydrogen or a straight or branched alkyl group of 1 to 6 C atoms or, in conjunction with N, a heterocyclic group with 5 or 6 ring C atoms; wherein R.sub.3 and R.sub.4 are identical or different, being selected from hydrogen, a straight or branched alkyl group of 1 to 6 C atoms, a cycloalkyl group with 5 or 6 C atoms, and phenyl; wherein R.sub.5 is hydrogen or a straight or branched C.sub.1 -C.sub.6 alkyl group, or a pharmaceutically-acceptable salt thereof, is disclosed.

  使用公式##STR1##中的一种脑缺血的预防和治疗方法，其中R.sub.1和R.sub.2是相同或不同，代表氢或由1到6个碳原子的直链或支链烷基基团，或者与N结合形成具有5或6个环碳原子的杂环基团；其中R.sub.3和R.sub.4是相同或不同，选自氢、由1到6个碳原子的直链或支链烷基基团、具有5或6个碳原子的环烷基基团和苯基；其中R.sub.5是氢或直链或支链C.sub.1-C.sub.6烷基基团，或其药用可接受盐。
• Inductive, Hyperconjugative and Frangomeric Effects in the Solvolysis of 1-Substituted 3-Bromoadamantanes. Polar effects IV
  作者：Walter Fischer、Cyril A. Grob

  DOI：10.1002/hlca.19780610510

  日期：1978.7.12

  Three kinds of polar substitutent effects are observable in the solvolyses of 1-R-substituted 3-bromoadamantanes (VI). This follows from the relationship between products, rate constants k in 80% ethanol, and the inductive substituent constants σ of the substituent R. Alkyl groups and electron-attracting substituents at C (1) control the rate by their inductive effects alone, since logk correlates closely

  1-R-取代的3-溴金刚烷（VI）的溶剂分解中可观察到三种极性取代基作用。这取决于产物，在80％的乙醇中的速率常数k和取代基R的感应取代基常数σ之间的关系。C（1）上的烷基和吸引电子的取代基仅通过它们的感应作用控制速率，因为log k与σ紧密相关。但是，共轭时（+ M）取代基或电离基团连接到C（1）。这些崇高的取代基作用归因于从C（3）的阳离子中心到C（1）的取代基的正电荷CC超共轭中继。当取代基是强电子供体（例如ø -和S - ），加速取代让位给然后由frangomeric效果控制异裂分裂，费率和产品。
• Amidoadamantanes and Method for Producing the Same
  申请人：Schreiner Peter R.

  公开号：US20090299096A1

  公开（公告）日：2009-12-03

  The invention relates to 1-formamido-adamantane derivatives of formula (I), which carry the substituents R 1 , R 2 or R 3 in 3, 5 and/or 7 position, the substituents being defined as follows: hydrogen, a linear or branched alkyl, alkenyl or alkinyl group with up to 6 C atoms, an aliphatic or aromatic, cyclic or heterocyclic hydrocarbon group with up to 10 carbon atoms, and formamides of hydrocarbons from the group of diamondoids, for example diamantane, triamantane, tetramantane and pentamantane, however, with the exception of 1-formamido-3,5-dimethyladamantane. The invention also relates to a method for the direct formation of formamide or acetamide of adamantane, adamantane derivatives with the aforementioned definition of substituents or of a hydrocarbon from the group of diamondoids, characterized by reacting the adamantane, the adamantane derivative or the diamondoid with formamide, acetamide or acetonitrile in concentrated acids, while avoiding SO 3 containing sulfuric acid or 100% azotic acid.

  本发明涉及公式（I）的1-甲酰基金刚烷衍生物，其在3、5和/或7位置携带取代基R1、R2或R3，所述取代基定义如下：氢、具有最多6个C原子的直链或支链烷基、烯基或炔基、具有最多10个碳原子的脂肪族或芳香族、环状或杂环烃基，以及来自金刚烷类群的烃的甲酰胺，例如金刚烷、三金刚烷、四金刚烷和五金刚烷，但不包括1-甲酰基-3,5-二甲基金刚烷。本发明还涉及一种直接形成金刚烷、金刚烷衍生物具有上述取代基定义或来自金刚烷类群的烃的甲酰胺或乙酰胺的方法，其特征在于将金刚烷、金刚烷衍生物或金刚烷类群与甲酰胺、乙酰胺或乙腈在浓酸中反应，避免含有SO3的硫酸或100％的硝酸。
• [EN] ADAMATANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTION<br/>[FR] DÉRIVÉS D'ADAMATANE POUR LE TRAITEMENT D'UNE INFECTION À FILOVIRUS
  申请人：ARISAN THERAPEUTICS

  公开号：WO2017127306A4

  公开（公告）日：2017-09-14
• Electronic control of face selection in the capture of radicals
  作者：Vani R. Bodepudi、William J. Le Noble

  DOI：10.1021/jo00006a009

  日期：1991.3

  A simple procedure is described which leads to the pure epimeric 2-(5-phenyl)adamantanecarboxylic acids E-1 and Z-1. Both acids upon treatment with bromine and mercuric oxide in carbon tetrachloride undergo the Hunsdiecker reaction to give the same mixture of E- and Z- 2-bromo-5-phenyladamantanes 4. 5-Phenyl-2-methyleneadamantane 6 undergoes reaction with bromotrichloromethane to give two diastereomeric adducts. In both instances, the major isomer results from the abstraction of a bromine atom by the zu face of the intermediate 5-phenyl-2-adamantyl radicals. The results mesh with other examples of face selection which we have previously ascribed to transition-state hyperconjugation. An additional case (hydride shift in a carbocation) was encountered in this work, as well as one apparent exception: the oxirane formation from adamantanone and sulfonium ylids. That result is attributed to thermodynamic control of the initial addition step.