4-butylidene-3-propyl-oxetan-2-one | 5659-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-butylidene-3-propyl-oxetan-2-one
• 英文别名: (+/-)-4-((Ξ)-butylidene)-3-propyl-oxetan-2-one；Propyl-keten-dimeres；(+/-)-4-((Ξ)-Butyliden)-3-propyl-oxetan-2-on；4-Butylidene-3-propyloxetan-2-one
• CAS: 5659-16-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DQQJQHVAPGGXHF-UHFFFAOYSA-N

物化性质

• 沸点：
  296.9±9.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醇 、 4-butylidene-3-propyl-oxetan-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 230.0~300.0 ℃ 、24.51 MPa 条件下， 生成 2-propyl-1,3-heptanediol
  参考文献：
  名称：

  The Catalytic Hydrogenation of Alkylketene Dimers

  摘要：

  DOI：

  10.1021/ja01133a511
• 作为产物：
  描述：

  戊酰氯 在 三乙胺 作用下， 以 正庚烷 为溶剂， 反应 73.0h， 以48.9%的产率得到4-butylidene-3-propyl-oxetan-2-one
  参考文献：
  名称：

  A High-Throughput Process for Valsartan

  摘要：

  With the redesign of three chemical steps, the throughput of the valsartan manufacturing process could be significantly increased, and with the substitution of chlorobenzene with cyclohexane in the bromination of 4'-methyl-biphenyl-2-carbonitrile (6) to 4'-bromomethyl-biphenyl-2-carbonitrfle (5), halogenated solvents are no longer used in the whole valsartan production process. The alkylation of (S)-2-amino-3-methyl-butyric acid benzyl ester (8) with 4'-bromomethyl-biphenyl-2-carbonitrfle (5), and the acylation of (S)-2-[(2'-cyano-biphenyl-4-ylmethyl)-aminol-3-methyl-butyric acid benzyl ester (4) to (S)-2-[(2'-cyano-biphenyl-4-ylmethyl)pentanoyl-amino]-3-methyl-butyric acid benzyl ester (3) were thoroughly modified. In the acylation of 4 to 3, N-ethyldiisopropylamine was replaced by aqueous sodium hydroxide by using the conditions of the Schotten-Baumann reaction, leading to a better quality of intermediate 3. In the alkylation of 8 with 5, N-ethyldiisopropylamine was indirectly replaced by aqueous sodium hydroxide. The reaction runs under homogenous conditions with (S)-2-amino-3-methyl-butyric acid benzyl ester (8) acting as acceptor for hydrobromic acid; recycling of 8 is performed by extraction with aqueous sodium hydroxide.

  DOI：

  10.1021/op700120n