(1R*,4S*,5S*,7S*)-1,2,3,4,7-pentachloro-5-phenylbicyclo[2.2.1]hept-2-ene

• 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: (1R*,4S*,5S*,7S*)-1,2,3,4,7-pentachloro-5-phenylbicyclo[2.2.1]hept-2-ene
• 英文别名: (1S,4R,5R,7R)-1,2,3,4,7-pentachloro-5-phenylbicyclo[2.2.1]hept-2-ene
• 化学式: C₁₃H₉Cl₅
• 分子量: 342.479
• InChiKey: RQGSNENYKVOODB-STRQVWJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  六氯环戊二烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 tin(ll) chloride 作用下， 以 丙酮 、 xylene 为溶剂， 反应 13.17h， 生成 (1R*,4S*,5S*,7S*)-1,2,3,4,7-pentachloro-5-phenylbicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Facial Selectivity in the Diels−Alder Reactions of 5-Chloro-, 5-Bromo-, and 5-Iodo-1,3-cyclopentadiene and Derivatives

  摘要：

  A variety of dienophiles was used to assess the facial selectivity of Diels-Alder reactions in a series of 1,3-cyclopentadiene derivatives (1-3, 6-10) in which chlorine, bromine, and iodine were plane-nonsymmetric atoms pitted against hydrogen or methyl at C-5. The results were rationalized in terms of the major factor controlling the facial selectivity being related to steric hindrance between the diene and the dienophile. Selectivity did not correlate with reactivity. Facial selectivity in the reactions with 4-phenyl-1,2,4-triazoline-3,5-dione as the dienophile was also influenced by a second significant factor, postulated to be filled-orbital repulsion with the halogen substituent.

  DOI：

  10.1021/jo961710j

文献信息

• Facial Selectivity in the Diels−Alder Reactions of 5-Chloro-, 5-Bromo-, and 5-Iodo-1,3-cyclopentadiene and Derivatives
  作者：Mark A. Wellman、Lori C. Burry、Johnathon E. Letourneau、John N. Bridson、David O. Miller、D. Jean Burnell

  DOI：10.1021/jo961710j

  日期：1997.2.1

  A variety of dienophiles was used to assess the facial selectivity of Diels-Alder reactions in a series of 1,3-cyclopentadiene derivatives (1-3, 6-10) in which chlorine, bromine, and iodine were plane-nonsymmetric atoms pitted against hydrogen or methyl at C-5. The results were rationalized in terms of the major factor controlling the facial selectivity being related to steric hindrance between the diene and the dienophile. Selectivity did not correlate with reactivity. Facial selectivity in the reactions with 4-phenyl-1,2,4-triazoline-3,5-dione as the dienophile was also influenced by a second significant factor, postulated to be filled-orbital repulsion with the halogen substituent.