(R,S)-trans-2-(2-Phenyl-1-cyclopropyl)-1,3-dioxolane | 136616-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,S)-trans-2-(2-Phenyl-1-cyclopropyl)-1,3-dioxolane
• 英文别名: 2-[(1R,2R)-2-phenylcyclopropyl]-1,3-dioxolane
• CAS: 136616-40-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: LSNKNYZBXJBNOE-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式肉桂醛 在 diethylzinc 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 2.5h， 生成 (R,S)-trans-2-(2-Phenyl-1-cyclopropyl)-1,3-dioxolane
  参考文献：
  名称：

  A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents

  摘要：

  A study comparing the rate of cyclopropanation of a range of olefins using (chloromethyl)- and (iodomethyl)zinc reagents is described. The (chloromethyl)zinc reagent derived from diethylzinc and chloroiodomethane is generally more reactive than the (iodomethyl)zinc analogue. The use of 1,2-dichloroethane as the solvent for these reactions was shown to be a crucial factor necessary to achieve clean, rapid, high-yielding cyclopropanations. The well-known directing effect of proximal oxygen substituents on the stereochemical outcome of "Simmons-Smith" cyclopropanations was shown to hold for the (chloromethyl)zinc reagent as well. The diethylzinc/chloroiodomethane reagent system in 1,2-dichloroethane should prove to be a valuable alternative to traditional (iodomethyl)zinc-based cyclopropanation reagents.

  DOI：

  10.1021/jo00025a007

文献信息

• Reactions of diazoalkanes with unsaturated compounds 15. Catalytic reactions of unsaturated carbonyl compounds and their derivatives with diazomethane
  作者：M. D. Khanova、R. M. Sultanova、S. S. Zlotskii、V. A. Dokichev、Yu. V. Tomilov

  DOI：10.1007/s11172-005-0348-7

  日期：2005.4

  The present study concerned with the influence of the nature of the acetal fragment in unsaturated compounds on the reactivity of the C=C bond in cyclopropanation reactions with diazomethane catalyzed by copper and palladium compounds. The acetal substituents at the α- or γ-position with respect to the C=C bond were found to exert an activating effect on the yields of cyclopropanation products compared

  本研究涉及不饱和化合物中缩醛片段的性质对铜和钯化合物催化的重氮甲烷环丙烷化反应中 C=C 键反应性的影响。发现与起始不饱和羰基化合物相比，C=C 键的 α-或 γ-位的缩醛取代基对环丙烷化产物的产率具有活化作用，后者产生 1,3-偶极环加成物CH2N2 作为副产品。双键的环丙烷化似乎由 Pd(acac)2 最有效地催化。