Carbamic acid, diethyl-, tetrahydro-2-hydroxy-2H-pyran-3-yl ester | 203436-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Carbamic acid, diethyl-, tetrahydro-2-hydroxy-2H-pyran-3-yl ester
• 英文别名: (2-hydroxyoxan-3-yl) N,N-diethylcarbamate
• CAS: 203436-51-5
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: STXIDCZWCAVHPF-UHFFFAOYSA-N

物化性质

• 沸点：
  328.0±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Carbamic acid, diethyl-, tetrahydro-2-hydroxy-2H-pyran-3-yl ester 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 生成 3,4-dihydro-2H-pyran-5-yl N,N-diethylcarbamate
  参考文献：
  名称：

  Synthesis of 2-Substituted Dihydropyran 3-O-Carbamates via Combined Metalation−Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  Treatment of 6-[(N,N-diethylcarbamoyl)oxy]-3,4-dihydro-2H-pyran (8) with t-BuLi followed by quench with a variety of electrophiles leads to 2-substituted products 9a-j (Table 2) in modest to good yields. The thereby obtained 2-boronic acid (11) and iodo (9j) derivatives undergo Suzuki-Migaura cross-coupling reactions to afford 2-aryl and -heteroaryl dihydropyran O-carbamates 12a-d in excellent yields.

  DOI：

  10.1021/jo971771x
• 作为产物：
  描述：

  2H-Pyran-3-ol, tetrahydro-2-(phenylmethoxy)-, (2R,3S)-rel- 在 palladium dichloride 氢气 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 39.0h， 生成 Carbamic acid, diethyl-, tetrahydro-2-hydroxy-2H-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of 2-Substituted Dihydropyran 3-O-Carbamates via Combined Metalation−Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  Treatment of 6-[(N,N-diethylcarbamoyl)oxy]-3,4-dihydro-2H-pyran (8) with t-BuLi followed by quench with a variety of electrophiles leads to 2-substituted products 9a-j (Table 2) in modest to good yields. The thereby obtained 2-boronic acid (11) and iodo (9j) derivatives undergo Suzuki-Migaura cross-coupling reactions to afford 2-aryl and -heteroaryl dihydropyran O-carbamates 12a-d in excellent yields.

  DOI：

  10.1021/jo971771x

文献信息

• Synthesis of 2-Substituted Dihydropyran 3-<i>O</i>-Carbamates via Combined Metalation−Suzuki−Miyaura Cross-Coupling Reactions
  作者：Justin F. Bower、Denis Guillaneux、Thai Nguyen、Poh Lee Wong、Victor Snieckus

  DOI：10.1021/jo971771x

  日期：1998.3.1

  Treatment of 6-[(N,N-diethylcarbamoyl)oxy]-3,4-dihydro-2H-pyran (8) with t-BuLi followed by quench with a variety of electrophiles leads to 2-substituted products 9a-j (Table 2) in modest to good yields. The thereby obtained 2-boronic acid (11) and iodo (9j) derivatives undergo Suzuki-Migaura cross-coupling reactions to afford 2-aryl and -heteroaryl dihydropyran O-carbamates 12a-d in excellent yields.