(S)-N-氯-1-苯基-1,2,3,4-四氢异喹啉 | 1422464-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: (S)-N-氯-1-苯基-1,2,3,4-四氢异喹啉
• 英文名称: (S)-N-chloro-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 1422464-27-4
• 化学式: C₁₅H₁₄ClN
• 分子量: 243.736
• InChiKey: DAIOPIZOFFMHBB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-N-氯-1-苯基-1,2,3,4-四氢异喹啉 在 sodium tetrahydroborate 、 D-酒石酸 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (S)-1-苯基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  One-Pot Racemization Process of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline: A Key Intermediate for the Antimuscarinic Agent Solifenacin

  摘要：

  (S)-(+)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, which is the key intermediate in preparing the urinary antispasmodic drug solifenacin, was racemized in quantitative yield by a simple one-pot procedure through N-chlorination with trichloroisocyanuric acid, conversion of the N-chloroamine into the imine hydrochloride, and reduction of the imine double bond. The racemized amine was successfully resolved by D-(-)-tartaric acid obtaining (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in 81% yield and with 96.7% ee and, from the crystallization mother liquors, the R enriched form. This was racemized by the same one-pot process and resolved by D-(-)-tartaric acid with the same efficiency. Such an approach to the racemization of 1-phenyl-1,2,3,4-tetrahydroisoquinoline can be industrially useful to recycle the waste R enantiomer resulting from the classical resolution used to obtain the S enantiomer on a large scale.

  DOI：

  10.1021/op300343q
• 作为产物：
  描述：

  (S)-1-苯基-1,2,3,4-四氢异喹啉 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以100%的产率得到(S)-N-氯-1-苯基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  One-Pot Racemization Process of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline: A Key Intermediate for the Antimuscarinic Agent Solifenacin

  摘要：

  (S)-(+)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, which is the key intermediate in preparing the urinary antispasmodic drug solifenacin, was racemized in quantitative yield by a simple one-pot procedure through N-chlorination with trichloroisocyanuric acid, conversion of the N-chloroamine into the imine hydrochloride, and reduction of the imine double bond. The racemized amine was successfully resolved by D-(-)-tartaric acid obtaining (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline in 81% yield and with 96.7% ee and, from the crystallization mother liquors, the R enriched form. This was racemized by the same one-pot process and resolved by D-(-)-tartaric acid with the same efficiency. Such an approach to the racemization of 1-phenyl-1,2,3,4-tetrahydroisoquinoline can be industrially useful to recycle the waste R enantiomer resulting from the classical resolution used to obtain the S enantiomer on a large scale.

  DOI：

  10.1021/op300343q