(S)-1-(2-hydroxyethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline | 142801-78-3

• 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)-1-(2-hydroxyethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-[(1S)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]ethanol
• CAS: 142801-78-3
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: HIHQNABFPBWAQZ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-hydroxyethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 70.17h， 生成 Methanesulfonic acid 2-[(S)-6-methoxy-2-(2-methyl-3-oxo-cyclopent-1-enyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-ethyl ester
  参考文献：
  名称：

  Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone

  摘要：

  Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed. Asymmetric alkylation with alpha-halo esters or beta-halo ethers gave 15 and 22, respectively, in high ee's. Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively. The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage. For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjupte reduction of the enone 5 with a copper hydride reagent method) requiring the presence of a silyl chloride affording 21. The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate. Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.

  DOI：

  10.1021/jo00043a036
• 作为产物：
  描述：

  1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-methoxy-1,2,3,4-tetrahydro-isoquinoline 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-1-(2-hydroxyethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone

  摘要：

  Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed. Asymmetric alkylation with alpha-halo esters or beta-halo ethers gave 15 and 22, respectively, in high ee's. Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively. The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage. For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjupte reduction of the enone 5 with a copper hydride reagent method) requiring the presence of a silyl chloride affording 21. The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate. Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.

  DOI：

  10.1021/jo00043a036