(±)-(6,7-dimethoxyisoquinolin-1-yl)(4-methoxyphenyl)methanol | 17656-57-4

• 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: (±)-(6,7-dimethoxyisoquinolin-1-yl)(4-methoxyphenyl)methanol
• 英文别名: (6,7-dimethoxyisoquinolin-1-yl)(4-methoxyphenyl)methanol；O,O-dimethyl-annocherin A；(6,7-Dimethoxyisoquinolin-1-yl)-(4-methoxyphenyl)methanol
• CAS: 17656-57-4
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: GYFCQRXTDVRRMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (6,7-dimethoxyisoquinolin-1-yl)(4-methoxyphenyl)methanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以68%的产率得到(±)-(6,7-dimethoxyisoquinolin-1-yl)(4-methoxyphenyl)methanol
  参考文献：
  名称：

  Transition metal-free Minisci reaction promoted by NCS, and TBHP: acylation of heteroarenes

  摘要：

  A method for acylation for heteroarenes under metal-free conditions has been described using NCS as an additive and TBHP as an oxidant. This method has been successfully employed in acylation of a variety of aldehyde with heteroarenes. The application of the method has been illustrated in synthesizing isoquinoline derived natural products. This strategy provides an efficient, mild and inexpensive method for acylation of heteroarenes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.065

文献信息

• A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines
  作者：Benedikt Melzer、Franz Bracher

  DOI：10.1039/c5ob00926j

  日期：——

  ols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines.

  甲氧基和苄氧基取代的异喹啉在C-1处用Knochel–Hauser碱进行区域选择性金属化，随后被芳族醛捕获，从而得到芳基（异喹啉-1-基）甲醇作为不同类型的苄基异喹啉生物碱的不同合成的基础。在还原条件下邻溴代类似物的光化学环化反应得到氧磷卟啉生物碱。从适当的异喹啉分两步或三步获得了九种苄基异喹啉生物碱和两种氧磷卟啉生物碱。
• Antiplatelet activity of benzylisoquinoline derivatives oxidized by cerium(IV) ammonium nitrate
  作者：Reen-Yen Kuo、Fang-Rong Chang、Chin-Chun Wu、Ramesh Patnam、Wei-Ya Wang、Ying-Chi Du、Yang-Chang Wu

  DOI：10.1016/s0960-894x(03)00477-3

  日期：2003.8

  Oxidation of 1-benzyl-3,4-dihydroisoquinolines with cerium(IV) ammonium nitrate (CAN) under mild condition yielded the mixture of corresponding 1-benzylisoquinolines (b-type) and 1-benzoylisoquinolines (a- or c-type) in an equal yields. The selective oxidation products (c-type) can be prepared by using MeCN instead of MeOH. In the antiplatelet assays, four inducers were employed, including AA, Col

  在温和条件下用硝酸铈（IV）铵（CAN）氧化1-苄基-3,4-二氢异喹啉，得到相应的1-苄基异喹啉（b型）和1-苯甲酰基异喹啉（a或c型）的混合物收益相等。选择性氧化产物（c型）可以通过使用MeCN代替MeOH来制备。在抗血小板测定中，采用了四种诱导剂，包括AA，Col，PAF和Thr。在PAF或Col诱导的血小板聚集中，属于a型和b型的化合物显示出比阿司匹林更强的抑制作用。
• DERIVATIVES OF PAPAVERINE THAT ARE EFFECTIVE HYPOXIC TUMOR RADIOSENSITIZERS
  申请人：Ohio State Innovation Foundation

  公开号：US20210163453A1

  公开（公告）日：2021-06-03

  Disclosed herein are compounds, compositions, and methods for inhibiting mitochondrial oxygen consumption in a cancerous tissue. The compounds, compositions, and methods can be used to treat a subject with hypoxic cancerous tissue.