2-氯-2-苯基金刚烷 | 29480-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-2-苯基金刚烷
• 英文名称: 2-chloro-2-phenyladamantane
• CAS: 29480-21-5
• 化学式: C₁₆H₁₉Cl
• 分子量: 246.78
• InChiKey: PURQNWPYAMMVHD-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  347.4±21.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-氯-2-苯基金刚烷 生成 2-(4-Nitro-phenyl)-adamantan-2-ol
  参考文献：
  名称：

  Solvolyses of tertiary .alpha.-arylcycloalkyl and -polycycloalkyl chlorides. Effects of ring size and substituents in the aryl ring on the solvolysis rates

  摘要：

  DOI：

  10.1021/ja00714a028
• 作为产物：
  描述：

  金刚烷酮 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-氯-2-苯基金刚烷
  参考文献：
  名称：

  通过配对电解实现净还原或氧化还原中性条件下的氘代脱卤

  摘要：

  氘的位点特异性引入在有机化学和药物化学中很重要。在此，我们提出了一种使用廉价的氧化氘作为氘源对芳基和杂芳基苄基卤化物进行氘代脱卤的电化学方法。我们还发现了一种连续配对电解方案，该方案允许在含硫底物的净还原反应和总体氧化还原中性反应之间切换。

  DOI：

  10.1002/anie.202218858

文献信息

• Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity
  作者：Christos Fytas、Grigoris Zoidis、Andrew Tsotinis、George Fytas、Mohsin A. Khan、Samar Akhtar、Khondaker M. Rahman、David E. Thurston

  DOI：10.1016/j.ejmech.2015.02.021

  日期：2015.3

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50=9.2 and 8.4 mu M, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 mu M, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts). (C) 2015 Published by Elsevier Masson SAS.
• Solvolysis of 2-aryl-2-chloroadamantanes. A new Y scale for benzylic chlorides
  作者：Kwang Ting Liu、Hun Chang Sheu

  DOI：10.1021/jo00009a018

  日期：1991.4

  A series of 2-aryl-2-chloroadamantanes 2, Ar = 4'-methylphenyl, 4'-fluorophenyl, phenyl, 3'-chlorophenyl, 3'-(trifluoromethyl)phenyl, and 4'-(trifluoromethyl)phenyl, were prepared, and the solvolytic rate constants in 23 solvents were measured. Significant deviation from linear log k - Y(Cl) plots (m = 1.002, R = 0.959) was observed, and some orders of reactivities, e.g., k(100M) > k(90E) > k(80A), were in the reverse order of Swain's solvent parameter B. Different extent of solvation to the cationic transition state was then likely to play an important role. Excellent linear correlations between the logarithms of the ks for any pair in 2a-2f were realized, and the best one was that with respect to 2d. A new Y scale, Y(BnCl), for the correlation of solvolytic reactivities of benzylic chlorides based on k(2d) was established accordingly. The observation of decreasing m values with increasing electron-attracting ability of the substituent on the aryl ring of 2 also suggested the importance of charge delocalizations.
• Kinetics and mechanism of unimolecular heterolysis of framework compounds: XX. Solvation and steric effects in heterolysis of 2-halo-2-alkyladamantanes in sulfolane and butanol
  作者：G. F. Dvorko、A. I. Vasil’kevich、K. V. Mikhal’chuk、I. V. Koshchii

  DOI：10.1134/s1070428007020066

  日期：2007.2

  Hetrolysis rate of 2-halo-2-phenyladamantanes in BuOH is 1000 times higher than the heterolysis rate C of 2-halo-2-methyladamantanes. The heterolysis rate in sulfolane does not depend on the substituent, but the phenyl group exhibits a negative steric effect.
• Baiocchi; Giannangeli, Bollettino Chimico Farmaceutico, 1971, vol. 110, # 4, p. 207 - 219
  作者：Baiocchi、Giannangeli

  DOI：——

  日期：——
• Solvolyses of tertiary .alpha.-arylcycloalkyl and -polycycloalkyl chlorides. Effects of ring size and substituents in the aryl ring on the solvolysis rates
  作者：Hiroshi Tanida、Tadahiko Tsushima

  DOI：10.1021/ja00714a028

  日期：1970.6