5-methyl-5-phenylacetyl-4-(pyrrolidin-1-yl)-5H-furan-2-one | 604809-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-methyl-5-phenylacetyl-4-(pyrrolidin-1-yl)-5H-furan-2-one
• 英文别名: 5-methyl-5-(2-phenylacetyl)-4-pyrrolidin-1-ylfuran-2-one
• CAS: 604809-28-1
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: QUQCPOHTGSIXLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-methyl-5-phenylacetyl-4-(pyrrolidin-1-yl)-5H-furan-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以98%的产率得到(5SR,1'SR)-5-(1'-hydroxy-2'-phenylethyl)-5-methyl-4-(pyrrolidin-1-yl)-5H-furan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 5-(1-hydroxyalkyl)-5-methyl-5H-furan-2-ones

  摘要：

  The reactivity of 5-methyl-4-(pyrrolidin-1-yl)-5H-furan-2-one with aldehydes and with acyl chlorides followed by reduction was studied. The aldol condensation gave predominantly the anti aldol product when the acylation-reduction sequence led exclusively to the syn product. The use of a chiral pyrrolidine, (S)-2-methoxymethylpyrrolidine (SMP), allowed the synthesis of enantio-enriched compounds, the acylation-reduction leading to the (R,R) addition product. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00937-2
• 作为产物：
  描述：

  4-(pyrrolidin-1-yl)-5H-furan-2-one 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 10.0h， 生成 5-methyl-5-phenylacetyl-4-(pyrrolidin-1-yl)-5H-furan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 5-(1-hydroxyalkyl)-5-methyl-5H-furan-2-ones

  摘要：

  The reactivity of 5-methyl-4-(pyrrolidin-1-yl)-5H-furan-2-one with aldehydes and with acyl chlorides followed by reduction was studied. The aldol condensation gave predominantly the anti aldol product when the acylation-reduction sequence led exclusively to the syn product. The use of a chiral pyrrolidine, (S)-2-methoxymethylpyrrolidine (SMP), allowed the synthesis of enantio-enriched compounds, the acylation-reduction leading to the (R,R) addition product. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00937-2