5-tert-butyladamantan-2-one | 84454-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-tert-butyladamantan-2-one
• CAS: 84454-67-1
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: ZALGHXJCZDONDI-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  287.7±8.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-tert-butyladamantan-2-one 、 反丁烯二腈 以 乙腈 为溶剂， 反应 48.0h， 生成 (2'S,3'R)-1-tert-butylspiro[adamantane-4,4'-oxetane]-2',3'-dicarbonitrile
  参考文献：
  名称：

  Stereochemistry of photocycloaddition of (E)-1,2-dicyano- and (Z)-1,2-diethoxyethylene to 5-substituted adamantanones

  摘要：

  The photocycloaddition of olefins to 5-substituted adamantanones produces two geometrically isomeric oxetanes in which the oxygen atom and the 5-substituent are in anti or syn positions. The substituent was varied from fluoro, chloro, bromo, hydroxyl, and phenyl to tert-butyl. Although the mechanisms of the reaction with electron-rich and electron-poor olefins are quite different, the product ratios are similar (approximately 60:40) in all instances. The preference of product formation from the attack on the zu face is discussed in terms of transition-state hyperconjugation.

  DOI：

  10.1021/jo00017a008
• 作为产物：
  描述：

  2-methoxy-5-tert-butyladamantane 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以46%的产率得到5-tert-butyladamantan-2-one
  参考文献：
  名称：

  Diastereofacial Selectivity in Reactions of 5-Substituted (X) Adamant-2-yl Cations:  Manifestations of Electron Demand

  摘要：

  A series of 5-substituted (X) 2,2-dimethoxyadamantanes (4, X = F, Cl, Br, COOCH3, OCH3, CH3, C6H5, p-NO2C6H4, p-BrC6H4, SiMe3, and SnMe3) as well as 2-methylene-5-tert-butyladamantane (6, Y = CH2; X = C(CH3)(3)) have been synthesized and characterized. Reduction of the. ketals 4 under ionic conditions with triethylsilane and phenylsilane provide pi-facial diastereoselectivities for hydride trapping of 5-substituted (X) 2-methoxyadamant-2-yl cations (1, R = OCH3 <-> 5). A comparison of this data with known diastereoselectivities for nucleophilic capture of tertiary and secondary 5-substituted (X) 2-adamantyl cations highlights that stereoselectivity in these systems is a function of electron demand. Diastereoselectivities for the hydrochlorination of 6 (Y = CH2, X = C(CH3)(3)) in CH2Cl2 and NO2CH3 have been determined and compared with the corresponding data for the silicon analogue (6, Y = CH2; X = SiMe3). Low electron demand coupled with the stereoelectronic requirement of double hyperconjugation appears the most likely explanation, rather than a long-range steric factor, for the total lack of stereoselectivity in the Cl- capture of the 2-methyl-5-(trimethylsilyl)adamant-2-yl cation (1, Y = CH2; X = SiMe3) in NO2CH3 as solvent.

  DOI：

  10.1021/jo970600p

文献信息

• 5-tert-Butyladamantan-2-one
  作者：W. J. Le Noble、Sushil Srivastava、Chiu K. Cheung

  DOI：10.1021/jo00155a034

  日期：1983.4
• LE, NOBLE, W. J.;SRIVASTAVA, SUSHIL;CHEUNG, CHIU, K., J. ORG. CHEM., 1983, 48, N 7, 1099-1101
  作者：LE, NOBLE, W. J.、SRIVASTAVA, SUSHIL、CHEUNG, CHIU, K.

  DOI：——

  日期：——