(1R,4S,7S)-8,8-Dichloro-4-phenyl-3,5-dioxa-bicyclo[5.1.0]octane | 651325-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1R,4S,7S)-8,8-Dichloro-4-phenyl-3,5-dioxa-bicyclo[5.1.0]octane
• CAS: 651325-74-5
• 化学式: C₁₂H₁₂Cl₂O₂
• 分子量: 259.132
• InChiKey: DUXQQJZGRPFNMY-URLYPYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4,7-二氢-2-苯基-1,3-二氧杂环庚 、 氯仿 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 144.0h， 生成 (1R,4S,7S)-8,8-Dichloro-4-phenyl-3,5-dioxa-bicyclo[5.1.0]octane 、 (1R,4R,7S)-8,8-Dichloro-4-phenyl-3,5-dioxa-bicyclo[5.1.0]octane
  参考文献：
  名称：

  Stereochemistry of Seven-Membered Heterocycles: XLIII. Steric Structure of Diastereoisomeric 8,8-Dichloro(dibromo)-4-R-3,5-dioxabicyclo[5.1.0]octanes

  摘要：

  Dichloro- and dibromocyclopropanation of 2-substituted 1,3-dioxacyclohept-5-enes according to Makosza resulted in formation of the corresponding 4-substituted 8,8-dichloro(dibromo)-3,5-dioxabicyclo[5.1.0]octanes in good yields. Ultrasonic activation of the process considerably shortened the reaction time. According to the C-13 NMR spectra, the chair-twist equilibrium is essentially displaced toward the chair conformer for the exo isomers and toward the twist conformer for the endo structures. Similar results were obtained by AMI semiempirical calculations which indicated that the (CClO)-O-... interaction largely determines the conformational equilibrium. The state of the diastereoisomer epimerization equilibrium depends on the size of the substituent at the acetal carbon atom.

  DOI：

  10.1023/b:rujo.0000003198.64663.ac