(1R*,4S*,5S*,7R*)-1,2,3,4,7-pentachloro-5-phenylbicyclo<2.2.1>hept-2-ene | 25242-85-7

• 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*,7R*)-1,2,3,4,7-pentachloro-5-phenylbicyclo<2.2.1>hept-2-ene
• 英文别名: (1S,4R,5R,7S)-1,2,3,4,7-pentachloro-5-phenylbicyclo[2.2.1]hept-2-ene
• CAS: 25242-85-7；25242-86-8
• 化学式: C₁₃H₉Cl₅
• 分子量: 342.479
• InChiKey: RQGSNENYKVOODB-NZBQSGDWSA-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

• 作为反应物：
  描述：

  三聚丙烯 、 (1R*,4S*,5S*,7R*)-1,2,3,4,7-pentachloro-5-phenylbicyclo<2.2.1>hept-2-ene 在 对苯二酚 作用下， 以 乙酸乙酯 为溶剂， 生成 (1S,4R,5R,7S)-1,2,3,4,7-Pentachloro-5-methyl-bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Stereochemistry of the Diels-Alder reaction. syn-anti Isomerism

  摘要：

  DOI：

  10.1021/ja01050a035
• 作为产物：
  描述：

  六氯环戊二烯 在 对二甲苯 、 tin(ll) chloride 作用下， 反应 2.0h， 生成 (1R*,4S*,5S*,7R*)-1,2,3,4,7-pentachloro-5-phenylbicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  Stereochemistry of the Diels-Alder reaction. syn-anti Isomerism

  摘要：

  DOI：

  10.1021/ja01050a035

文献信息

• Steric Control in the Diels-Alder Reaction
  作者：Kazuyoshi Seguchi、Akira Sera、Kazuhiro Maruyama

  DOI：10.1246/bcsj.49.3558

  日期：1976.12

  investigated, and the rates of the reaction and the endo : exo adduct distributions were determined. The introduction of a chlorine atom at the C5 position of cyclopentadiene resulted in an enhanced endo preference for substituents in the adducts, despite the depressed reactivity of the diene. This is contrary to what is to be expected from the so-called “selectivity-reactivity relationship in the Diels-Alder

  研究了聚氯环戊二烯与取代乙烯的 Diels-Alder 反应，并确定了反应速率和内：外加合物分布。尽管二烯的反应性降低，但在环戊二烯的 C5 位置引入氯原子导致加合物中取代基的内向偏好增强。这与所谓的“狄尔斯-阿尔德反应中的选择性-反应性关系”所预期的相反。这项工作的结果是根据二烯的 C5-氯原子与亲二烯体的取代基之间的空间相互作用来解释的。
• 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.