1-[(Pent-4-enoyl)oxy]pyridine-2(1H)-thione | 113882-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[(Pent-4-enoyl)oxy]pyridine-2(1H)-thione
• 英文别名: (2-sulfanylidenepyridin-1-yl) pent-4-enoate
• CAS: 113882-49-8
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: FGGXVWWGCQBJKP-UHFFFAOYSA-N

物化性质

• 沸点：
  293.2±33.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(Pent-4-enoyl)oxy]pyridine-2(1H)-thione 、 丙烯腈 以 二氯甲烷 为溶剂， 以60%的产率得到2-(3-cyano-3-pyridin-2-ylsulfanylpropyl)cyclopentane-1-carbonitrile
  参考文献：
  名称：

  基于N-羟基-2-硫代吡啶酮的酰基衍生物的自由基反应对碳-碳键形成的进一步研究

  摘要：

  通过仔细地排除氧，可以将由N-羟基-2-硫代吡啶酮的O-酰基衍生物的W灯光解所产生的碳自由基有效地添加到甲基乙烯基酮中。由戊-4-烯酸延伸至自由基提供了环戊烷衍生物的另一种合成方法。还报道了与其他亲电子烯烃的类似添加。

  DOI：

  10.1016/s0040-4039(00)88890-5
• 作为产物：
  描述：

  1-氧化-2-巯基吡啶 、 4-戊烯酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(Pent-4-enoyl)oxy]pyridine-2(1H)-thione
  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

• BARTON, DEREK H. R.;SARMA, JADAB C., TETRAHEDRON LETT., 31,(1990) N4, C. 1965-1968
  作者：BARTON, DEREK H. R.、SARMA, JADAB C.

  DOI：——

  日期：——
• MAILLARD B.; KHARRAT A.; GARDRAT C., NEW J. CHEM., 11,(1987) N 1, 7-13
  作者：MAILLARD B.、 KHARRAT A.、 GARDRAT C.

  DOI：——

  日期：——
• Further studies on carbon-carbon bond formation based on the radical reactions of acyl derivatives of N-hydroxy-2-thiopyridone
  作者：Derek H.R. Barton、Jadab C. Sarma

  DOI：10.1016/s0040-4039(00)88890-5

  日期：1990.1

  By careful exclusion of oxygen, carbon radicals, generated from the W lamp photolysis of O-acyl derivatives of N-hydroxy-2-thiopyridone, can be added efficiently to methylvinyl ketone. Extension to the radical from pent-4-enoic acid provides another synthesis of cyclopentane derivatives. Analogous additions with other electrophilic olefins are also reported.

  通过仔细地排除氧，可以将由N-羟基-2-硫代吡啶酮的O-酰基衍生物的W灯光解所产生的碳自由基有效地添加到甲基乙烯基酮中。由戊-4-烯酸延伸至自由基提供了环戊烷衍生物的另一种合成方法。还报道了与其他亲电子烯烃的类似添加。
• 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.