(S)-(-)-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol | 128707-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)-(-)-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol
• 英文别名: (4S)-2-methyl-4-phenyl-1,3-dihydroisoquinolin-4-ol
• CAS: 128707-50-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: KEVNEIPRCIYVOT-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-羟基-2-甲基-4-苯基-1,2,3,4-四氢异喹啉 生成 (S)-(-)-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol
  参考文献：
  名称：

  KIHARA, MASARU;KASHIMOTO, MINORU;KABAYASHI, SHIGERU;ISHIDA, YUKIO;MORITOK+, J. MED. CHEM., 33,(1990) N, C. 2283-2286

  摘要：

  DOI：

文献信息

• KIHARA, MASARU;KASHIMOTO, MINORU;KABAYASHI, SHIGERU;ISHIDA, YUKIO;MORITOK+, J. MED. CHEM., 33,(1990) N, C. 2283-2286
  作者：KIHARA, MASARU、KASHIMOTO, MINORU、KABAYASHI, SHIGERU、ISHIDA, YUKIO、MORITOK+

  DOI：——

  日期：——
• Resolution, absolute stereochemistry, and enantioselectivity of 2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol
  作者：Masaru Kihara、Minoru Kashimoto、Shigeru Kobayashi、Yukio Ishida、Hideki Moritoki、Zenei Taira

  DOI：10.1021/jm00170a037

  日期：1990.8

  Racemic 2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ol (PI-OH) (1) was found to be an effective potentiator of the contractile response of norepinephrine (NE) on rat anococcygeus muscle. This paper describes the resolution of racemic PI-OH by an HPLC method to give the optically pure enantiomers (+)-1 and (-)-1. The absolute configuration of (+)-1 was R as determined by CD analysis and by single-crystal X-ray diffractometric analysis of the methiodide 6 derived from (+)-1. Examination of the effects of the enantiomers to potentiate the contraction of the rat anococcygeus muscle by NE showed a high degree of enantioselectivity. The NE potentiation was found to reside exclusively in (R)-(+)-1; the activity ratio being 21 at 3 x 10(-6) M, whereas (S)-(-)-1 did not show any potentiating and inhibiting activity.