1-chloro-1,3,3-trimethylcyclopentane | 200573-80-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 1-chloro-1,3,3-trimethylcyclopentane
• CAS: 200573-80-4
• 化学式: C₈H₁₅Cl
• 分子量: 146.66
• InChiKey: PPJKDZXGXMTPTO-UHFFFAOYSA-N

物化性质

• 沸点：
  158.9±9.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3,3-trimethyl-1-cyclopentanol 在 盐酸 作用下， 以 正戊烷 为溶剂， 反应 0.67h， 以94%的产率得到1-chloro-1,3,3-trimethylcyclopentane
  参考文献：
  名称：

  Structural effects of the Grunwald–Winstein correlations in the solvolysis of some simple tertiary alkyl chlorides

  摘要：

  The rates of solvolysis in various solvents at 25 degrees C were determined for five tertiary alkyl chlorides: 2-chloro-2,4,4-trimethylpentane (4), 2-chloro-2,4-dimethylpentane, 2-chloro-2-methylpentane, 1-chloro-1,3,3-trimethylcyclopentane (7) and 1-chloro-1-methylcyclopentane. The rate data were analysed on the basis of the original and extended Grunwald-Winstein-type equation [log(k/k(0))=mY(Cl)+c and log(k/k(0))=lN(T)+mY(Cl+)c] and the results were compared with those reported for 2-chloro-2-methylpropane (1) and 2-chloro-2,3,3-trimethylbutane (3). The rate data for 4 in 18 solvents give an excellent correlation with l=0.00+/-0.02 and m=0.74+/-0.01. The neopentyl group in 4 more effectively shields the rear-side of the reaction center than the tert-butyl group in 3 that is correlated by l=0.10+/-0.04 and m=0.81+/-0.04. The rate ratio between 4 and 1 at 25 degrees C is 275 in TFE and predicted to increase to 950 in TFA. The previous 4/1 rate ratio of 21 in 80% ethanol evidently underestimates the B-strain effect on the solvolysis rate of 4 by a factor of at least 40, The remote methyl groups in 7 works to increase rear-side shielding without increasing B-strain, The marked difference in the effect of the remote methyl groups between 4 and 7 suggests that the leaving chloride ion in 4 takes a locus that is nearly antiperiplanar to the tert-butyl group. (C) 1997 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199710)10:10<717::aid-poc941>3.0.co;2-y