山缘草定碱 | 550-49-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 邻苯二甲酸异喹啉类
• 中文名称: 山缘草定碱
• 中文别名: 藤荷包牡丹定鹼
• 英文名称: (+/-)-adlumidine
• 英文别名: rac-adlumidine；adlumidine；(RS)-6-((RS)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-8-one；(+/-)-capnoidine；(+/-)-Capnoidin；(1S,9S) u. (1R,9R)-Adlumidin；(6S)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
• CAS: 550-49-2
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: IYGYMKDQCDOMRE-ROUUACIJSA-N

物化性质

• 熔点：
  236-237°
• 比旋光度：
  D25 +116.2° (c = 22 in chloroform)
• 沸点：
  542.3±50.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险等级：
  6.1(b)

反应信息

• 作为反应物：
  描述：

  山缘草定碱 在 super hydride 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

  摘要：

  A concise diastereotioselective strategy for the synthesis of noscapine, bicuculiine, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to immium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from airline 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3). (C) 2010 Elseviet Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.104
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 氯化亚砜 、 锌铜偶 、 叠氮基三甲基硅烷 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 乙腈 、 均三甲苯 、 苯 为溶剂， 反应 47.0h， 生成 山缘草定碱
  参考文献：
  名称：

  Slemon, Clarke E.; Hellwig, Louise C.; Ruder, Jean-Pierre, Canadian Journal of Chemistry, 1981, vol. 59, p. 3055 - 3060

  摘要：

  DOI：

文献信息

• Synthesis of Phthalideisoquinoline and Protoberberine Alkaloids and Indolo[2,1-<i>a</i>]isoquinolines in a Divergent Route Involving Palladium(0)-Catalyzed Carbonylation¹
  作者：Kazuhiko Orito、Mamoru Miyazawa、Ryo Kanbayashi、Masao Tokuda、Hiroshi Suginome

  DOI：10.1021/jo982451w

  日期：1999.9.1

  hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4-dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium

  通过在含碳酸钾的N，N-二甲基甲酰胺中加热得到2,3,8,9-或2,3,9,10-烷氧基取代的5,6-来实现赤氨基氨基醇19的一锅环化。 dihydroindolo [2,1-a] isoquinolines 3，具有二苯并吡咯啉碱生物碱的独特四环骨架特征。类似地，发现在过量碳酸钾存在下，钯（0）催化1-（2'-溴苄基）四氢异喹啉21的羰基化反应生成8-氧代berbines 22，经氢化铝锂还原后可转化为原小ber碱生物碱4 。具有二苯并吡咯啉碱生物碱的独特四环骨架特征。类似地，发现在过量碳酸钾存在下，钯（0）催化1-（2'-溴苄基）四氢异喹啉21的羰基化反应生成8-氧代berbines 22，经氢化铝锂还原后可转化为原小ber碱生物碱4 。具有二苯并吡咯啉碱生物碱的独特四环骨架特征。类似地，发现在过量碳酸钾存在下，钯（0）催化1-（2'-溴苄基）四氢异喹啉21的羰基化反应生成8-氧代berbines
• Egenine: a possible intermediate in phthalideisoquinoline biogenesis
  作者：Belkis Gözler、Tekant Gözler、Maurice Shamma

  DOI：10.1016/s0040-4020(01)91831-9

  日期：1983.1

  (+)-Egenine (4), the first phthalideisoquinoline hemiacetal isolated form a natural source has been found in Fumaria vaillantii Loisel. (Fumariaceae). (+)-Egenine may act as the immediate biogenetic precursor of the accompanying alkaloid (+)-bicuculline (1).

  （+）-Egenine（4），是从天然来源分离出的第一种邻苯二甲酰异喹啉半缩醛，已在Fumaria vaillantii Loisel中发现。（伞形科）。（+）-Egenine可能是伴随的生物碱（+）-biculculline（1）的直接生物遗传前体。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。
• Blaha,K. et al., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 2328 - 2340
  作者：Blaha,K. et al.

  DOI：——

  日期：——
• Chiefari, John; Janowski, Wit K.; Prager, Rolf H., Heterocycles, 1989, vol. 28, # 2, p. 863 - 867
  作者：Chiefari, John、Janowski, Wit K.、Prager, Rolf H.

  DOI：——

  日期：——