3-chloro-2,2-difluoro-4a-(2-pyridylthio)-1,2,4a,5,6,7,8,8a-octahydronaphthalene | 197149-40-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-2,2-difluoro-4a-(2-pyridylthio)-1,2,4a,5,6,7,8,8a-octahydronaphthalene
• 英文别名: 2-[(6-Chloro-7,7-difluoro-1,2,3,4,8,8a-hexahydronaphthalen-4a-yl)sulfanyl]pyridine
• CAS: 197149-40-9
• 化学式: C₁₅H₁₆ClF₂NS
• 分子量: 315.815
• InChiKey: IHLAQCZJDCNYTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-2,2-difluoro-4a-(2-pyridylthio)-1,2,4a,5,6,7,8,8a-octahydronaphthalene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以79%的产率得到3,3-Difluoro-4,4a,5,6,7,8-hexahydronaphthalen-2-one
  参考文献：
  名称：

  Cyclization of Hindered Fluorinated Dichloro(5- and 6-)alkenyl Radicals. Structural Effects of Olefins on the Selective Formation of 5-exo and 6-endo Cyclization Products

  摘要：

  Reaction of 3-butenyl radicals generated by photolysis of variously substituted Barton esters (both open-chain 1a-d and cyclohexyl 1e-h) with CF2=CCl2 gave a mixture of cyclized products (cyclopentanes 6 and 8 and cyelohexanes 7 and 9) as well as noncyclized products (4 and 5) in various ratios depending on the substitution pattern at the olefinic moiety. The product ratios of [cyclization (6 + 7 + 8 + 9):noncyclization (5)] for 1 with more alkyl substituents on the CC double bond were greater than those for 1 with fewer substituents. The products ratio of [5-exo (6 + 8):6-endo (7 + 9)] was influenced by a steric effect. Photoreaction of Barton ester 2 with CF2-CCl2 gave a mixture of cyclohexanes 16 and 17 as well as noncyclized 14 and 15. Dehydrochlorination of decalins 7g and 7h followed by oxidation of sulfide and [2,3]sigmatropic rearrangement of the allyl sulfoxide gave octahydronaphthalenones 23 and 27, respectively.

  DOI：

  10.1021/jo970639u
• 作为产物：
  描述：

  1-氧化-2-巯基吡啶 在 1,1-二氯-2,2-二氟乙烯 、 potassium tert-butylate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-chloro-2,2-difluoro-4a-(2-pyridylthio)-1,2,4a,5,6,7,8,8a-octahydronaphthalene
  参考文献：
  名称：

  Cyclization of Hindered Fluorinated Dichloro(5- and 6-)alkenyl Radicals. Structural Effects of Olefins on the Selective Formation of 5-exo and 6-endo Cyclization Products

  摘要：

  Reaction of 3-butenyl radicals generated by photolysis of variously substituted Barton esters (both open-chain 1a-d and cyclohexyl 1e-h) with CF2=CCl2 gave a mixture of cyclized products (cyclopentanes 6 and 8 and cyelohexanes 7 and 9) as well as noncyclized products (4 and 5) in various ratios depending on the substitution pattern at the olefinic moiety. The product ratios of [cyclization (6 + 7 + 8 + 9):noncyclization (5)] for 1 with more alkyl substituents on the CC double bond were greater than those for 1 with fewer substituents. The products ratio of [5-exo (6 + 8):6-endo (7 + 9)] was influenced by a steric effect. Photoreaction of Barton ester 2 with CF2-CCl2 gave a mixture of cyclohexanes 16 and 17 as well as noncyclized 14 and 15. Dehydrochlorination of decalins 7g and 7h followed by oxidation of sulfide and [2,3]sigmatropic rearrangement of the allyl sulfoxide gave octahydronaphthalenones 23 and 27, respectively.

  DOI：

  10.1021/jo970639u

文献信息

• Cyclization of Hindered Fluorinated Dichloro(5- and 6-)alkenyl Radicals. Structural Effects of Olefins on the Selective Formation of 5-<i>exo</i> and 6-<i>endo</i> Cyclization Products
  作者：Takashi Okano、Hidemasa Ishihara、Nobuyuki Takakura、Hiroyasu Tsuge、Shoji Eguchi、Hiroshi Kimoto

  DOI：10.1021/jo970639u

  日期：1997.10.1

  Reaction of 3-butenyl radicals generated by photolysis of variously substituted Barton esters (both open-chain 1a-d and cyclohexyl 1e-h) with CF2=CCl2 gave a mixture of cyclized products (cyclopentanes 6 and 8 and cyelohexanes 7 and 9) as well as noncyclized products (4 and 5) in various ratios depending on the substitution pattern at the olefinic moiety. The product ratios of [cyclization (6 + 7 + 8 + 9):noncyclization (5)] for 1 with more alkyl substituents on the CC double bond were greater than those for 1 with fewer substituents. The products ratio of [5-exo (6 + 8):6-endo (7 + 9)] was influenced by a steric effect. Photoreaction of Barton ester 2 with CF2-CCl2 gave a mixture of cyclohexanes 16 and 17 as well as noncyclized 14 and 15. Dehydrochlorination of decalins 7g and 7h followed by oxidation of sulfide and [2,3]sigmatropic rearrangement of the allyl sulfoxide gave octahydronaphthalenones 23 and 27, respectively.