(S)-tert-butyl 1-((2S,3R)-2-hydroxy-3-(methoxycarbonyl)-5-methylhexyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1415385-78-2

• 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)-tert-butyl 1-((2S,3R)-2-hydroxy-3-(methoxycarbonyl)-5-methylhexyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
• 英文别名: tert-butyl (1S)-1-[(2S,3R)-2-hydroxy-3-methoxycarbonyl-5-methylhexyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1415385-78-2
• 化学式: C₂₅H₃₉NO₇
• 分子量: 465.587
• InChiKey: OLBYGMJSSISKRM-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 1-((2S,3R)-2-hydroxy-3-(methoxycarbonyl)-5-methylhexyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 methyl (2R)-2-[(1S)-2-[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]-1-hydroxyethyl]-4-methylpentanoate
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-dihydrotetrabenazine

  摘要：

  A highly stereoselective synthesis of (-)-dihydrotetrabenazine has been accomplished using (R)-tert-butanesulfinamide as a chiral source. The synthesis involves the allylation of chiral N-sulfinyl imine followed by ring closure of the resulting secondary amide with a tethered halide and the Evans-Aldol reaction as key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.017
• 作为产物：
  描述：

  4-甲基戊酸 在 sodium methylate 、 三甲基乙酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.25h， 生成 (S)-tert-butyl 1-((2S,3R)-2-hydroxy-3-(methoxycarbonyl)-5-methylhexyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-dihydrotetrabenazine

  摘要：

  A highly stereoselective synthesis of (-)-dihydrotetrabenazine has been accomplished using (R)-tert-butanesulfinamide as a chiral source. The synthesis involves the allylation of chiral N-sulfinyl imine followed by ring closure of the resulting secondary amide with a tethered halide and the Evans-Aldol reaction as key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.017

文献信息

• The stereoselective total synthesis of (−)-dihydrotetrabenazine
  作者：N. Siva Senkar Reddy、A. Srinivas Reddy、J.S. Yadav、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2012.10.017

  日期：2012.12

  A highly stereoselective synthesis of (-)-dihydrotetrabenazine has been accomplished using (R)-tert-butanesulfinamide as a chiral source. The synthesis involves the allylation of chiral N-sulfinyl imine followed by ring closure of the resulting secondary amide with a tethered halide and the Evans-Aldol reaction as key steps. (C) 2012 Elsevier Ltd. All rights reserved.