(+/-)-(1R,2'S)-1-(2'-hydroxy-2'-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

• 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: (+/-)-(1R,2'S)-1-(2'-hydroxy-2'-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
• 英文别名: (RS)-1-((SR)-2-hydroxy-2-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；(1S)-2-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]-1-phenylethanol
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: YCFTZQSGANFCHN-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R,2'S)-1-(2'-hydroxy-2'-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 在 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到
  参考文献：
  名称：

  Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3-oxathiazino[4,3-a]isoquinolines

  摘要：

  Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side-chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3-oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis(1)-trans-cis(2) type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2007.11.054
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉盐酸盐 在 sodium hydroxide 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 36.0h， 生成 (+/-)-(1R,2'S)-1-(2'-hydroxy-2'-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  1-和2-苯基取代的1,3-恶嗪基[4,3- a ]异喹啉衍生物的合成和立体化学研究

  摘要：

  从1'-或2'-苯基取代的1-（2'-羟基乙基）-6,7-二甲氧基-1,2,3,4-四氢异喹啉对映体起始3和6，4 -未取代的和4-（p（-硝基苯基）-和4-氧取代的1-苯基-和2-苯基-9,10-二甲氧基-2 H，4 H -1,6,7,11b-四氢-1,3-恶嗪[4,3 -一个]异喹啉（7 - 12）中制备。产物的相对构型和主要构象由NMR光谱，量子化学计算确定，对于（2 R ∗，4 S ∗，11b R ∗）-9,10-二甲氧基-4-（p-硝基苯基）-2-苯基-2 H，4 H -1,6,7,11b-四氢-1,3-恶嗪基[4,3- a ]异喹啉（11），通过X射线衍射。

  DOI：

  10.1016/s0040-4020(03)00149-2

文献信息

• Asymmetric Synthesis and Enantiospecificity of Binding of 2-(1,2,3,4-Tetrahydro-1-isoquinolyl)-ethanol Derivatives to μ and κ Receptors
  作者：Klaus Th. Wanner、Ilona Praschak、Georg Höfner、Herbert Beer

  DOI：10.1002/ardp.19963290104

  日期：——

  reactions, served as starting compounds. Upon reduction of 5a—c and ent‐5a—c the amido alcohols l‐6a—c, u‐6a—c, ent‐l‐6a—c and ent‐u‐6a—c were obtained. Hydrolysis of these compounds yielded the secondary amino alcohols l‐7a—c, u‐7a—c, ent‐l‐7a—c and ent‐u‐7a—c and upon reductive methylation of l‐7b—c, u‐7b—c, ent‐l‐7b—c and ent‐u‐7b—c with CH2O and NaCNBH3 the tertiary amino alcohols l‐7d—e, u‐7d—e, ent‐l‐7d—e

  许多 2-(1,2,3,4-四氢-1-异喹啉基)-乙醇衍生物 7a-e 已经以非对映体和对映体纯形式合成，并评估了它们对 μ 和 κ 阿片受体的结合亲和力。酰胺酮 5a-c 和 ent-5a-c 可通过将 3b 和 ent-3b 用于不对称亲电酰胺烷基化反应而获得，用作起始化合物。5a-c和ent-5a-c还原得到酰胺醇l-6a-c、u-6a-c、ent-l-6a-c和ent-u-6a-c。这些化合物的水解产生仲氨基醇 l-7a-c、u-7a-c、ent-l-7a-c 和 ent-u-7a-c，并且在 l-7b-c、u-7b 的还原甲基化后—C、ent-l-7b —c 和 ent-u-7b —c 与 CH2O 和 NaCNBH3 叔氨基醇 l-7d-e、u-7d-e、ent-l-7d-e 和 ent-u-得到7d-e。
• Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3-oxathiazino[4,3-a]isoquinolines
  作者：Ildikó Schuster、Andreas Koch、Matthias Heydenreich、Erich Kleinpeter、László Lázár、Ferenc Fülöp

  DOI：10.1016/j.molstruc.2007.11.054

  日期：2008.10

  Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side-chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3-oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis(1)-trans-cis(2) type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines. (C) 2007 Elsevier B.V. All rights reserved.
• Synthesis and stereochemical studies of 1- and 2-phenyl-substituted 1,3-oxazino[4,3-a]isoquinoline derivatives
  作者：Matthias Heydenreich、Andreas Koch、László Lázár、István Szatmári、Reijo Sillanpää、Erich Kleinpeter、Ferenc Fülöp

  DOI：10.1016/s0040-4020(03)00149-2

  日期：2003.3

  Starting from the 1′- or 2′-phenyl-substituted 1-(2′-hydroxyethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline diastereomers 3 and 6, 4-unsubstituted and 4-(p-nitrophenyl)- and 4-oxo-substituted 1-phenyl- and 2-phenyl-9,10-dimethoxy-2H,4H-1,6,7,11b-tetrahydro-1,3-oxazino[4,3-a]isoquinolines (7–12) were prepared. The relative configurations and the predominant conformations of the products were determined

  从1'-或2'-苯基取代的1-（2'-羟基乙基）-6,7-二甲氧基-1,2,3,4-四氢异喹啉对映体起始3和6，4 -未取代的和4-（p（-硝基苯基）-和4-氧取代的1-苯基-和2-苯基-9,10-二甲氧基-2 H，4 H -1,6,7,11b-四氢-1,3-恶嗪[4,3 -一个]异喹啉（7 - 12）中制备。产物的相对构型和主要构象由NMR光谱，量子化学计算确定，对于（2 R ∗，4 S ∗，11b R ∗）-9,10-二甲氧基-4-（p-硝基苯基）-2-苯基-2 H，4 H -1,6,7,11b-四氢-1,3-恶嗪基[4,3- a ]异喹啉（11），通过X射线衍射。