(+/-)-canadaline | 62475-57-4

• 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: (+/-)-canadaline
• 英文别名: 2,3-dimethoxy-6-(6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)-benzaldehyde；(+/-)-Canadalin；(+)-Canadalin；Canadalin；2,3-dimethoxy-6-[(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl]benzaldehyde
• CAS: 62475-57-4
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: ROAHDZJDHGLGBA-UHFFFAOYSA-N

物化性质

• 沸点：
  514.8±50.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 1-(2-chloromethyl-3,4-dimethoxyphenylmethyl)-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline-2-carboxylate 在 aluminum oxide 、 lithium aluminium tetrahydride 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 65.5h， 生成 (+/-)-canadaline
  参考文献：
  名称：

  Hanaoka, Miyoji; Nagami, Kazuyoshi; Inoue, Mitsuru, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 8, p. 2685 - 2690

  摘要：

  DOI：

文献信息

• A new group of isoquinoline alkaloids
  作者：Maurice Shamma、Alan S. Rothenberg、Gamini S. Jayatilake、S. Fazal Hussain

  DOI：10.1016/0040-4020(78)88096-x

  日期：1978.1

  configuration of (−)-1 was determined by chemical correlation with (+)-rhoeagenine methiodide (20). The chirality of the alkaloid (+)-canadaline (10a) has also been established by analogy to (+)-corydalisol (11b). (−)-Peshawarine (1), (+)-canadaline (10a), (+)-corydalisol (11b), and aobamine (10b), as well as hypecorine (22) and hypecorinine (23), are members of a new group of isoquinoline alkaloids, the secoberbines

  新的异喹啉生物碱（-）-peshawarine（1）已从Hypecoum parviflorum Kar中分离出来。＆Kir。（罂粟科）。它从黄连（6b）外消旋形式的合成涉及一种环状半缩醛的新方法，其中关键步骤是使用氯甲酸乙酯将醛（±）-氨基苯甲酰胺（10b）转化为半缩醛12b。（±）-香豆酚（11b）和（±）-加拿大茶碱（10a）也是第一次合成。（-）-1的绝对构型是通过与（+）-二十碳四氢呋喃碱（Rhoeagenine methiodide）（20）的化学相关性确定的。生物碱（+）-加拿大碱（10a）也类似于（+）-corydalisol（11b）所建立。（-）-Peshawarine（1），（+）-canadaline（10a），（+）-corydalisol（11b）和aobamine（10b）以及hypecorine（22）和hypecorinine（23）是a的成员一组新的异喹啉生物碱，七柏树酯。
• Compositions and methods for making noscapine and synthesis intermediates thereof
  申请人：Willow BioSciences Inc.

  公开号：US10793885B2

  公开（公告）日：2020-10-06

  Methods for the manufacture of the therapeutic chemical compound noscapine and noscapine synthesis intermediates comprising contacting a noscapine pathway precursor selected from a first canadine derivative, a first papaveroxine derivative and narcotine hemiacetal with at least one of the enzymes selected from the group CYP82Y1, CYP82X1, AT1, CYP82X2, OMT, CXE1 and NOS.

  生产治疗用化学合成物诺卡平和诺卡平合成中间体的方法，包括将选自第一卡那定衍生物、第一罂粟碱衍生物和麻醉品半缩醛的诺卡平途径前体与选自CYP82Y1、CYP82X1、AT1、CYP82X2、OMT、CXE1和NOS组的至少一种酶接触。
• Hanaoka,M. et al., Heterocycles, 1979, vol. 12, p. 497 - 498
  作者：Hanaoka,M. et al.

  DOI：——

  日期：——
• PRODUCTION OF ISOQUINOLINE ALKALOIDS AND FLAVONOIDS IN PLANT CELL CULTURES OF GOLDENSEAL (HYDRASTIS CANADENSIS)
  申请人：DIANAPLANTSCIENCES INC.

  公开号：US20160208299A1

  公开（公告）日：2016-07-21

  Natural product preparations of isoquinoline alkaloids are obtained from plant callus cells of goldenseal, Hydrastis canadensis , grown in suspension cell culture. The natural product preparations can be extracted from the cells and/or obtained from the culture medium in which the cells are grown. Accordingly, callus cell lines can be selected to grow in suspension culture, produce desirable levels and/or ratios of isoquinoline alkaloids, and/or release the isoquinoline alkaloids into the liquid medium. The level and/or ratio of certain isoquinoline alkaloids, such as hydrastine and/or berberine produced by the cells and/or released into the medium can be different than those found in native plants or plant parts (e.g., rhizomes) from which the cells were derived. For instance, cell lines can be selected to increase the production and/or ratio of hydrastine to berberine, or vice versa.
• COMPOSITIONS AND METHODS FOR MAKING NOSCAPINE AND SYNTHESIS INTERMEDIATES THEREOF
  申请人：Willow BioSciences Inc.

  公开号：US20210155963A1

  公开（公告）日：2021-05-27

  Methods that may be used for the manufacture of the therapeutic chemical compound noscapine and noscapine synthesis intermediates. Compounds useful for the synthesis of noscapine are also provided.