(+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline | 74035-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-methoxy-5-[[(1R)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol
• CAS: 74035-73-7
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: NYGNBPLXMNXERU-MRXNPFEDSA-N

物化性质

• 沸点：
  482.1±45.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 C₁₉H₂₀NO₃⁽¹⁺⁾*Cl^(1-)
  参考文献：
  名称：

  SUBSTITUTED BERBINES AND THEIR SYNTHESIS

  摘要：

  本发明提供了替代苯并啉化合物，以及用于合成替代苯并啉化合物的工艺，以及合成替代苯并啉化合物所使用的中间体。还提供了使用替代苯并啉来抑制癌细胞生长的方法。

  公开号：

  US20150099772A1
• 作为产物：
  描述：

  1-(3-Hydroxy-4-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-isochinolin 生成 (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  RICE, K. C.

  摘要：

  DOI：

文献信息

• (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof
  申请人：Mallinckrodt LLC

  公开号：US10363251B2

  公开（公告）日：2019-07-30

  The present invention provides (+)-morphinans comprising Toll-like receptor 9 (TLR9) antagonist activity, as well as methods for using the (+)-morphinans to treat a variety of disorders.

  本发明提供了包含Toll样受体9（TLR9）拮抗剂活性的(+)-吗啡烷，以及使用(+)-吗啡烷治疗各种疾病的方法。
• (+)-morphinans as antagonists of Toll-like receptor 9 and therapeutic uses thereof
  申请人：Mallinckrodt LLC

  公开号：US11142502B2

  公开（公告）日：2021-10-12

  The present invention provides (+)-morphinans comprising Toll-like receptor 9 (TLR9) antagonist activity, as well as methods for using the (+)-morphinans to treat pain. Also provided are pharmaceutical combination compositions comprising a (+)-morphinan and an opioid agonist/monoamine reuptake inhibitor, as well as methods for using the combination compositions to treat pain.

  本发明提供了包含Toll样受体9（TLR9）拮抗剂活性的(+)-吗啡烷，以及使用(+)-吗啡烷治疗疼痛的方法。本发明还提供了包含(+)-吗啡南和阿片激动剂/单胺再摄取抑制剂的药物组合物，以及使用该组合物治疗疼痛的方法。
• Meuzelaar, Gerrit J.; Van Vliet, Michiel C. A.; Maat, Leendert, European Journal of Organic Chemistry, 1999, # 9, p. 2315 - 2321
  作者：Meuzelaar, Gerrit J.、Van Vliet, Michiel C. A.、Maat, Leendert、Sheldon, Roger A.

  DOI：——

  日期：——
• General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes
  作者：Masato Kitamura、Yi Hsiao、Masako Ohta、Masaki Tsukamoto、Tetsuo Ohta、Hidemasa Takaya、Ryoji Noyori

  DOI：10.1021/jo00081a007

  日期：1994.1

  In the presence of a small amount of RuX(2)[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4-tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100 %) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used fbr synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.
• WO2008/73389
  申请人：——

  公开号：——

  公开（公告）日：——