4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxybutan-2-one | 193804-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxybutan-2-one
• CAS: 193804-06-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: RLAHYWMTYABUQY-VIFPVBQESA-N

物化性质

• 沸点：
  284.7±20.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxybutan-2-one 、 (氯亚甲基)三苯基正膦 在 双(三甲基硅烷基)氨基钾 作用下， 生成 (4S)-4-[2-(2,5-dihydrofuran-3-yl)ethyl]-2,2-dimethyl-1,3-dioxolane 、 (5R)-8-(methoxymethyl)-2,2-dimethyl-1,3-dioxaspiro[4.4]non-8-ene
  参考文献：
  名称：

  Improved chemoselectivity in intramolecular alkylidene carbene CH insertion

  摘要：

  The alkylidene carbene generated by chloromethylenation/alpha-elimination of 1 proceeds with a high degree of selectivity for methoxy C-H insertion over methine insertion, to give 2. The carbene generated with trimethylsilyldiazomethane results in an approximately 1:1 mixture of 2 and 3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01081-2
• 作为产物：
  描述：

  4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxybutan-2-ol 在 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-methoxybutan-2-one
  参考文献：
  名称：

  Improved chemoselectivity in intramolecular alkylidene carbene CH insertion

  摘要：

  The alkylidene carbene generated by chloromethylenation/alpha-elimination of 1 proceeds with a high degree of selectivity for methoxy C-H insertion over methine insertion, to give 2. The carbene generated with trimethylsilyldiazomethane results in an approximately 1:1 mixture of 2 and 3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01081-2

文献信息

• Improved chemoselectivity in intramolecular alkylidene carbene CH insertion
  作者：Douglass F. Taber、Thomas E. Christos

  DOI：10.1016/s0040-4039(97)01081-2

  日期：1997.7

  The alkylidene carbene generated by chloromethylenation/alpha-elimination of 1 proceeds with a high degree of selectivity for methoxy C-H insertion over methine insertion, to give 2. The carbene generated with trimethylsilyldiazomethane results in an approximately 1:1 mixture of 2 and 3. (C) 1997 Elsevier Science Ltd.