双环[3.2.1]辛烷-1-甲酰氯 | 58541-35-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 双环[3.2.1]辛烷-1-甲酰氯
• 英文名称: 1-bicyclo{3.2.1}octanecarbonyl chloride
• 英文别名: Bicyclo[3.2.1]octane-1-carbonyl chloride
• CAS: 58541-35-8
• 化学式: C₉H₁₃ClO
• 分子量: 172.655
• InChiKey: ZXVWPLDPXIKWQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  双环[3.2.1]辛烷-1-甲酰氯 在 ammonium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 bicyclo<3.2.1>octane-1-carboxamide
  参考文献：
  名称：

  Della, Ernest W.; Pigou, Paul E.; Taylor, Dennis K., Australian Journal of Chemistry, 1993, vol. 46, # 1, p. 63 - 72

  摘要：

  DOI：
• 作为产物：
  描述：

  双环[3.2.1]辛烷-1-羧酸 在 氯化亚砜 作用下， 反应 1.0h， 生成 双环[3.2.1]辛烷-1-甲酰氯
  参考文献：
  名称：

  Della, Ernest W.; Pigou, Paul E.; Taylor, Dennis K., Australian Journal of Chemistry, 1993, vol. 46, # 1, p. 63 - 72

  摘要：

  DOI：

文献信息

• Della, Ernest W.; Tsanaktsidis, John, Australian Journal of Chemistry, 1989, vol. 42, # 1, p. 61 - 69
  作者：Della, Ernest W.、Tsanaktsidis, John

  DOI：——

  日期：——
• Alkyl migration in an iron(II) alkylidene: a new route to a stabilized bridgehead olefin
  作者：Robert S. Bly、M. Mahmun Hossain、Lukasz Lebioda

  DOI：10.1021/ja00305a051

  日期：1985.9
• Photochemical .alpha. cleavage of ketones in solution. VIII. Photochemical reactivity of some bridgehead phenyl ketones
  作者：H. G. Heine、W. Hartmann、F. D. Lewis、R. T. Lauterbach

  DOI：10.1021/jo00873a005

  日期：1976.5
• [Fp-.eta.1-(1-polycycloalkyl)methylidene]+ to [Fp-.eta.2-(1-homopolycycloalkene)]+ rearrangement. Carbon migration in iron(II) alkylidenes. A new route to stabilized bridgehead olefins
  作者：Robert S. Bly、Ruta K. Bly、Mahmun M. Hossain、Lukasz. Lebioda、Muthukrishna. Raja

  DOI：10.1021/ja00231a023

  日期：1988.11
• 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.