2-环丙基丙基-(2) | 24299-93-2

• 分子结构分类: 有机化合物 - 碳氢化合物
• 中文名称: 2-环丙基丙基-(2)
• 中文别名: 2-环丙基丙基-(2)
• 英文名称: 2-Cyclopropyl-propyl-(2)
• CAS: 24299-93-2
• 化学式: C₆H₁₁
• 分子量: 83.1533
• InChiKey: IEQVHYPZBBJJFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-环丙基丙基-(2) 生成 4-甲基-戊-3-烯基
  参考文献：
  名称：

  Bowry, Vincent W.; Lusztyk, Janusz; Ingold, Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5687 - 5698

  摘要：

  DOI：
• 作为产物：
  描述：

  以 环己烷 为溶剂， 生成 2-环丙基丙基-(2)
  参考文献：
  名称：

  Kinetics of Reactions of Cyclopropylcarbinyl Radicals and Alkoxycarbonyl Radicals Containing Stabilizing Substituents: Implications for Their Use as Radical Clocks

  摘要：

  The rate constants for rearrangement of alpha-substituted cyclopropylcarbinyl radicals have been measured by nitroxide radical-trapping (NPT). Those bearing methyl, dimethyl, or cyclopropyl substituents undergo ring opening 2-3 times more slowly than does cyclopropylmethyl radical, but the reaction is essentially irreversible under the conditions used. Phenyl and tert-butoxycarbonyl alpha-substituents retard the rate of ring opening more strongly and enhance the rate of ring closure of the corresponding substituted but-3-enyl radicals. Thus for c-C(3)H(5)CHPh at 60 degrees C, k(ring open) = 5.4 x 10(5) s(-1), k(ring close) = 1.5 x 10(7) s(-1), and the equilibrium favors the ring closed form (K-equil = 0.04). The implications of the possible reversibility of the ring opening of substituted cyclopropylcarbinyl radicals for cyclopropane probe studies of metal hydride reduction and other chemical/biochemical reactions are assessed. Most of the cyclopropylcarbinyl radicals were generated from tert-butyl peroxyglyoxaletes (ROC(O)CO(3)Bu(t)) via alkoxycarbonyl radicals (ROCO). This method allowed the determination of the rate constants for decarboxylation of ROCO when R is t-Bu, PhCH(2), c-C(3)H(5)CMe(2), c-C(3)H(5)CHMe, (c-C3H5)(2)CH, or c-C3H5CHC6H(5).

  DOI：

  10.1021/ja00086a003

文献信息

• Oxidation of Isopropylcyclopropane by Chromyl Chloride:  Ring-Opened Products Support a Hydrogen Atom Abstraction Mechanism
  作者：Kun Wang、James M. Mayer

  DOI：10.1021/jo962348b

  日期：1997.6.1

  abstraction from the substrate. The resulting dimethylcyclopropylcarbinyl radical can either be trapped by CrO(2)Cl(2) (to form 1 and 2) or ring-open to give 4-methyl-3-pentenyl radical, which reacts with CrO(2)Cl(2) to form 3 and 4 as well as further oxidized products. The oxidation of isopropylcyclopropane by MnO(4)(-) in pyridine was also examined. Acetone, an expected ring-opened product, was the

  铬酰氯（CrO（2）Cl（2））与纯异丙基环丙烷在65摄氏度下反应，产生深色沉淀，至少有20种有机产物。观察到环丙基产物和开环产物：2-环丙基-2-氯丙烷（1，基于铬的产率为0.4％），2-环丙基-2-丙醇（2，为0.2％），5-氯-2-甲基-2-戊烯（3，0.3％）和4-甲基-3-戊烯-1-醇（4，0.5％）以及其他开环产品。合成了1-4个真实的样品，并将它们的GC和GC / MS数据与反应混合物进行了比较。GC / MS根据其m / z和碎裂模式初步分配了其他有机产物（5-10）。当CrO（2）Cl（2）的初始浓度从0.3增加到1.12 M时，（1 + 2）与（3 + 4）的比率增加2倍。该反应也在气相中进行，基本上观察到了液相反应的所有产物。产物是通过涉及从底物上最初提取氢原子的机理来解释的。生成的二甲基环丙基羰基自由基可以被CrO（2）Cl（2）捕获（形成1和2），也可以开环生成4
• Clocking Tertiary Cyclopropylcarbinyl Radical Rearrangements¹
  作者：Paul S. Engel、Shu-Lin He、J. T. Banks、K. U. Ingold、J. Lusztyk

  DOI：10.1021/jo961685h

  日期：1997.3.1

  Three independent methods have been employed to estimate the rate constant, k(1), for ring-opening of the 2-cyclopropyl-2-propyl radical, 1, at room temperature. These three estimates are based on chemical trapping of 1 and the ring-opened 4-methylpent-3-ene-1-yl radical by thiophenol (k(1) = (1.6(5) +/- 0.4(1)) x 10(7) M(-1) s(-1)), 9-azabicyclo[3.3.1]nonane-N-oxyl (k(1) = (1.7(6) +/- 0.3(4)) x 10(7) M(-1) s(-1)) and 2,2,6,6-tetramethylpiperidine-N-oxyl (k(1) = (2.1 +/- 0.4) x 10(7) M(-1) s(-1)) and absolute rate constants for nonrearranging radicals structurally related to 1. The mean value for k(1) ((1.8(4) +/- 0.4) x 10(7) M(-1) s(-1)) should be used when 1 is employed as a tertiary alkyl free radical clock at ambient temperatures.