片螺素T | 189083-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 片螺素T
• 英文名称: Lamellarin T
• 英文别名: 14-(3-hydroxy-4-methoxyphenyl)-3-hydroxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one；7-hydroxy-12-(3-hydroxy-4-methoxyphenyl)-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-3-one
• CAS: 189083-78-1
• 化学式: C₃₀H₂₇NO₉
• 分子量: 545.546
• InChiKey: NKDLSUHQYRACEX-UHFFFAOYSA-N

物化性质

• 熔点：
  283-284 °C
• 沸点：
  834.3±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  片螺素T 在 4-二甲氨基吡啶 碳酸氢钠 、 水 、 柠檬酸 、 magnesium sulfate 作用下， 以 乙酸酐 、 吡啶 、 乙酸乙酯 为溶剂， 反应 26.0h， 以giving the title compound (47 mg, 83%) as a white solid mp 251-2° C的产率得到14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Preparation of fused polycyclic alkaloids by ring closure of azomethine ylides, novel compounds thereof and their use as chemotherapeutic agents

  摘要：

  一种制备通式为的化合物或其药学上可接受的衍生物和盐，外消旋体、异构体和/或互变异构体的方法，包括环化通式为的偶氮甲基亚胺：其中，A是环状或非环状基团；Z是碳或杂原子；n从0、1、2或3中选择；W、X和Y可以相同也可以不同，每个都从氢；可选取代的烷基、烯基、炔基、氨基、烷氧基、烯氧基、炔氧基、芳基、烷硫基、杂环基；羧基、羧酯、羧酰胺、酰基、酰氧基、巯基、卤素、硝基、硫酸酯、磷酸酯、氰基和可选的保护羟基；或W和X与它们附着的氮和碳原子一起形成饱和或不饱和的含氮杂环基团，该基团可以是可选取代的或可选融合到饱和或不饱和的碳环基团、芳基或杂环基团。

  公开号：

  US20050154004A1
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 碳酸氢钠 、 sodium carbonate 、 溶剂黄146 、 乙二胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、517.11 kPa 条件下， 反应 47.0h， 生成 片螺素T
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h

文献信息

• Selective Cleavage of Isopropyl Aryl Ethers by Aluminum Trichloride^†
  作者：Martin G. Banwell、Bernard L. Flynn、Scott G. Stewart

  DOI：10.1021/jo9808526

  日期：1998.11.1
• US7557118B2
  申请人：——

  公开号：US7557118B2

  公开（公告）日：2009-07-07
• Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings
  作者：Poonsakdi Ploypradith、Thaninee Petchmanee、Poolsak Sahakitpichan、Nichole D. Litvinas、Somsak Ruchirawat

  DOI：10.1021/jo061810h

  日期：2006.12.1

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.
• Preparation of fused polycyclic alkaloids by ring closure of azomethine ylides, novel compounds thereof and their use as chemotherapeutic agents
  申请人：——

  公开号：US20030208076A1

  公开（公告）日：2003-11-06

  A method for the preparation of a compound of general Formula: 1 or pharmaceutically acceptable derivatives and salts, racemates, isomers and/or tautomers thereof comprising cyclizing an azomethine ylide of general Formula: 2 wherein A is a cyclic or non-cyclic group; Z is a carbon or a heteroatom; n is selected from 0, 1, 2 or 3; W, X and Y may be the same or different and each are selected from hydrogen; optionally substituted alkyl, alkenyl, alkynyl, amino, alkoxy, alkenoxy, alkynoxy, aryl, alkylthio, heterocyclyl; carboxy, carboxy ester, carboxamido, acyl, acyloxy, mercapto, halogen, nitro, sulfate, phosphate, cyano and optionally protected hydroxy; or W and X, together with the nitrogen and carbon atoms to which they are attached, form a saturated or unsaturated nitrogen containing heterocyclic group which may be optionally substituted or optionally fused to a saturated or unsaturated carbocyclic group, aryl group or heterocyclic group is provided.

  一种制备通式1化合物或其药学上可接受的衍生物、盐、外消旋体、异构体和/或互变异构体的方法，包括环化通式2的偶氮甲基亚胺，其中A是环状或非环状基团；Z是碳或杂原子；n从0、1、2或3中选择；W、X和Y可以相同也可以不同，每个都是氢；可选择取代的烷基、烯基、炔基、氨基、烷氧基、烯氧基、炔氧基、芳基、烷硫基、杂环基；羧基、羧酯、羧酰胺、酰基、酰氧基、巯基、卤素、硝基、硫酸酯、磷酸酯、氰基和可选择保护的羟基；或者W和X与它们所连接的氮和碳原子一起形成饱和或不饱和的含氮杂环基团，该基团可以选择取代或可选择融合到饱和或不饱和的碳环基团、芳基或杂环基团中。