1,3-二噁烷-2-酮,4-(5,6-二氢-2H-吡喃-3-基)- | 113495-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 中文名称: 1,3-二噁烷-2-酮,4-(5,6-二氢-2H-吡喃-3-基)-
• 英文名称: 4-(5,6-dihydro-2H-pyran-3-yl)-1,3-dioxan-2-one
• 英文别名: 4-(3,6-dihydro-2H-pyran-5-yl)-1,3-dioxan-2-one
• CAS: 113495-28-6
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: WJSNNEULKBASOD-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±42.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲基苯磺酰异氰酸酯 、 1,3-二噁烷-2-酮,4-(5,6-二氢-2H-吡喃-3-基)- 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以98%的产率得到N-(p-Toluenesulfonyl)-5-(5'-oxa-1'-cyclohexenyl)-6-aza-2-oxacyclohexan-1-one
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1,3-Hydroxyl Amines via Palladium-Catalyzed Carbonate-Carbamate Transformation with Unique Stereoselectivity: Synthesis of 3-Amino-4-penten-1-ols

  摘要：

  The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). H-1 NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.

  DOI：

  10.1021/jo00085a039
• 作为产物：
  描述：

  1-(3,6-二氢-2H-吡喃-5-基)丙烷-1,3-二醇 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-二噁烷-2-酮,4-(5,6-二氢-2H-吡喃-3-基)-
  参考文献：
  名称：

  Efficient Synthesis of 2-Vinyl-γ-butyrolactones and 2-Vinyl-γ-butyrolactams by Palladium-Catalyzed Decarboxylative Carbonylation

  摘要：

  4-乙烯基-1,3-二恶烷-2-酮（环状碳酸酯）在 CO（大多数情况下为 1 个大气压）下，通过 Pd(0) 物质的催化作用进行脱羧-羰基化，生成 2-乙烯基-γ-丁内酯良好的产量。 6-乙烯基四氢-2H-1,3-恶嗪-2-酮（环状氨基甲酸酯）的反应过程取决于氮原子上的取代基。当它是H或Ts(和COPh)时，获得2-乙烯基-γ-丁内酰胺或6-氨基-3-己烯酸酯。环状N-苄基氨基甲酸酯不具有反应性。反式2,3-二取代内酯和内酰胺分别立体选择性地由碳酸酯和氨基甲酸酯产生，无论其立体化学如何。

  DOI：

  10.1246/bcsj.65.97

文献信息

• Synthesis of 2-vinyl-γ-butyrolactones by the palladium-catalyzed decarboxylative carbonylation of 3-vinyl-1-oxo-2,6-dioxacyclohexanes
  作者：Yoshinao Tamaru、Takashi Bando、Makoto Hojo、Zen-ichi Yoshida

  DOI：10.1016/s0040-4039(00)96336-6

  日期：——
• TAMARU, YOSHINAO;BANDO, TAKASHI;HOJO, MAKOTO;YOSHIDA, ZEN-ICHI, TETRAHEDRON LETT., 28,(1987) N 30, 3497-3500
  作者：TAMARU, YOSHINAO、BANDO, TAKASHI、HOJO, MAKOTO、YOSHIDA, ZEN-ICHI

  DOI：——

  日期：——
• Regio- and Stereoselective Synthesis of 1,3-Hydroxyl Amines via Palladium-Catalyzed Carbonate-Carbamate Transformation with Unique Stereoselectivity: Synthesis of 3-Amino-4-penten-1-ols
  作者：Takashi Bando、Hiroto Harayama、Yoshimasa Fukazawa、Motoo Shiro、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00085a039

  日期：1994.3

  The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). H-1 NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.
• Efficient Synthesis of 2-Vinyl-γ-butyrolactones and 2-Vinyl-γ-butyrolactams by Palladium-Catalyzed Decarboxylative Carbonylation
  作者：Takashi Bando、Shuji Tanaka、Keigo Fugami、Zen-ichi Yoshida、Yoshinao Tamaru

  DOI：10.1246/bcsj.65.97

  日期：1992.1

  4-Vinyl-1,3-dioxan-2-ones (cyclic carbonates) undergo decarboxylation-carbonylation by the catalysis of Pd(0) species under CO (in most cases, 1 atm) to provide 2-vinyl-γ-butyrolactones in good yields. The course of the reaction of 6-vinyltetrahydro-2H-1,3-oxazin-2-ones (cyclic carbamates) depends on the substituent on the nitrogen atom. When it is H or Ts (and COPh), 2-vinyl-γ-butyrolactams or 6-amino-3-hexenoic acid esters are obtained. Cyclic N-benzylcarbamates are unreactive. trans-2,3-Disubstituted lactones and lactams arise stereoselectively from carbonates and carbamates, irrespective of their stereochemistry, respectively.

  4-乙烯基-1,3-二恶烷-2-酮（环状碳酸酯）在 CO（大多数情况下为 1 个大气压）下，通过 Pd(0) 物质的催化作用进行脱羧-羰基化，生成 2-乙烯基-γ-丁内酯良好的产量。 6-乙烯基四氢-2H-1,3-恶嗪-2-酮（环状氨基甲酸酯）的反应过程取决于氮原子上的取代基。当它是H或Ts(和COPh)时，获得2-乙烯基-γ-丁内酰胺或6-氨基-3-己烯酸酯。环状N-苄基氨基甲酸酯不具有反应性。反式2,3-二取代内酯和内酰胺分别立体选择性地由碳酸酯和氨基甲酸酯产生，无论其立体化学如何。