(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde | 1014651-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde
• CAS: 1014651-21-8
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: QAFOZLMFEAYJGB-HXUSNMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde 、 (R)-(-)-4-甲基苯亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到(S)-4-methylbenzenesulfinic acid 1-{(4S,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-yl}methylideneamine
  参考文献：
  名称：

  Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E

  摘要：

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

  DOI：

  10.1021/ol702962z
• 作为产物：
  描述：

  (4S,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E

  摘要：

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

  DOI：

  10.1021/ol702962z