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1-hydroxy-3,3-dimethylbicyclo[2.2.2]oct-2-yl benzoate | 110977-41-8

中文名称
——
中文别名
——
英文名称
1-hydroxy-3,3-dimethylbicyclo[2.2.2]oct-2-yl benzoate
英文别名
——
1-hydroxy-3,3-dimethylbicyclo[2.2.2]oct-2-yl benzoate化学式
CAS
110977-41-8
化学式
C17H22O3
mdl
——
分子量
274.36
InChiKey
ZDMZFNDNYHKHKF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.17
  • 重原子数:
    20.0
  • 可旋转键数:
    2.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.59
  • 拓扑面积:
    46.53
  • 氢给体数:
    1.0
  • 氢受体数:
    3.0

反应信息

  • 作为反应物:
    参考文献:
    名称:
    评估2-亚甲基和2-氧代取代基的π-共轭作用对双环桥头衍生物溶剂分解中碳正离子稳定性的影响
    摘要:
    与刚性较强的2-亚甲基双环[2.2.2]辛-1-基阳离子相比,初始的2-亚甲基双环[3.2.2]壬-1-基阳离子通过烯丙基结合稳定在4 kcal / mol。与此相反,在2-氧代双环[3.2.2]壬-1-基阳离子中未检测到由于羰基π-共轭引起的明显稳定,表明在叔α-酮基阳离子中π-共轭稳定的重要性不高。
    DOI:
    10.1016/s0040-4039(00)82470-3
  • 作为产物:
    参考文献:
    名称:
    Ring-Expansion of Bridgehead Aldehydes with 1-Adamantanecarbonyl Cation or Benzoyl Trifluoromethanesulfonate: A New Route to Bicyclic and Tricyclic 1,2-Diols
    摘要:
    在三氟甲磺酸存在下,桥头醛与由 1-金刚烷阳离子和一氧化碳生成的 1-金刚烷羰基阳离子或与三氟甲磺酸苯甲酰酯发生酰化反应,会使醛环扩张一个碳原子。将反应混合物加水处理后,可得到在邻接碳上含有酰氧基的桥头醇,皂化后可得到邻接二醇,总产率很高。例如,双环[2.2.1]庚烷-1-甲醛可生成双环[2.2.2]辛烷-1,2-二醇,而其他方法很难获得这种物质。
    DOI:
    10.1055/s-1987-28022
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文献信息

  • Solvolyses of 2-Oxo Bridgehead Compounds:  A Critical Examination of π-Conjugative Stabilization of α-Carbonyl Carbocations
    作者:Ken'ichi Takeuchi、Yasushi Ohga、Masayasu Yoshida、Keizo Ikai、Tadashi Shibata、Midori Kato、Akio Tsugeno
    DOI:10.1021/jo970454n
    日期:1997.8.1
    The methodology of changing ring flexibility to detect the pi-conjugative stabilization of bridgehead carbocations has been applied to eight 2-oxo (X = O) bridgehead carbocations. On the basis of the solvolytic behavior observed in kinetics and product analyses, the eight 2-oxo bridgehead substrates were classified into three categories: three substrates solvolyzing without ion-pair return that leads to primary isomers (class A), three substrates that form primary isomers by ion-pair return during solvolysis (class B), and two substrates that undergo solvent addition to the carbonyl group to form hemiacetals during solvolysis (class C). It was concluded that the substrates of class C could not be used for the present purpose. Essentially constant ethanolysis rate ratios, k(X = O)/k(X = H-2), of 10(-8.2)-10(-8.7) at 25 degrees C were obtained between four 2-oxo substrates in classes A and B and the corresponding parent unsubstituted ones. The result was interpreted to suggest that the pi-conjugative stabilization of tertiary alpha-carbonyl carbocations is negligibly small, if present. Slightly more negative k(X = O)/k(X = H-2) values of 10(-9.7) and 10(-9.2) for highly flexible bicyclo[4.2.2]dec-1-yl and bicyclo[4.3.1]dec-l-yl systems, respectively, were attributed to complex conformations in the ground and incipient carbocations. PM3 calculations on some 2-methylene and 2-oxo bridgehead carbocations supported the experimental results. Comparison of the solvolysis rates of 1,1,3,3-tetramethyl-2-oxobutyl mesylate with those of 1,1,3,3-tetramethylbutyl mesylate estimated from the rates of the corresponding chloride also failed to support the pi-conjugative stabilization of alpha-carbonyl carbocations.
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