(6-Methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid isopropyl ester | 142801-71-6

• 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: (6-Methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid isopropyl ester
• 英文别名: propan-2-yl 2-(6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate
• CAS: 142801-71-6
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: KWKIAARUNJXZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6-Methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid isopropyl ester 在 hydrido(triphenylphosphine)copper(I) hexamer 、 三氟乙酸 作用下， 以 甲苯 、 苯 为溶剂， 反应 6.2h， 生成 (3aR,10bS)-8-Methoxy-12-triethylsilanyloxy-1,2,3,3a,5,6,10b,11-octahydro-cyclopenta[5,6]pyrido[2,1-a]isoquinoline
  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

文献信息

• Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone
  作者：A. I. Meyers、Todd R. Elworthy

  DOI：10.1021/jo00043a036

  日期：1992.8

  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.