Tylocrebrin | 30061-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Tylocrebrin
• 英文别名: tylocrebrine；(+/-)-Tylocrebrine；2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
• CAS: 30061-35-9
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: YFEPHJVWLFGWKH-UHFFFAOYSA-N

物化性质

• 熔点：
  227-229 °C (decomp)
• 沸点：
  559.9±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二甲氧基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三氟代氧化钒(V) 、 叔丁基锂 、 sodium carbonate 、 三氟乙酸 、 三氟乙酸酐 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 19.17h， 生成 Tylocrebrin
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954

文献信息

• Compounds and compositions for treating infection
  申请人：Chepkwony Paul Kiprono

  公开号：US20090069277A1

  公开（公告）日：2009-03-12

  Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

  来自14种肯尼亚植物的化合物，包括 Dovyalis abyssinica 和 Clutia robusta 的根部已经被鉴定和分离，它们的用途也被公开了。
• Synthesis of (±)-septicine and (±)-tylophorine by regioselective [3 + 2] cycloaddition
  作者：Hideo Iida、Masao Tanaka、Chihiro Kibayashi

  DOI：10.1039/c39830000271

  日期：——

  The synthesis of (±)-septicine and (±)-tylophorine, using 1,3-dipolar cycloaddition and intramolecular photocyclisation reactions as key steps, is described.

  描述了使用1，3-偶极环加成和分子内光环化反应作为关键步骤的（±）-败血碱和（±）-酪氨酸的合成。
• Modular Syntheses of Phenanthroindolizidine Natural Products
  作者：Young-In Jo、Martin D. Burke、Cheol-Hong Cheon

  DOI：10.1021/acs.orglett.9b01397

  日期：2019.6.7

  A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki–Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki–Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride,

  提出了一种高度简洁的菲咯啉吲哚全合成策略。芳基硼酸与邻-溴芳基N-甲基亚氨基二乙酸酯（MIDA）硼酸酯的一锅迭代Suzuki-Miyaura反应，然后与合适的吡啶溴化物提供的邻-氮杂-三联苯进行第二次Suzuki-Miyaura反应。随后使三键饱和，用甲磺酰氯处理，并还原所得的二氢吲哚并鎓环，得到六氢吲哚并酮。最终的钒催化氧化电环化仅在三个色谱柱分离操作中即可提供所需的生物碱。
• Tylophorine Analogs as Antitumor Agents
  申请人：Lee Kuo-Hsiung

  公开号：US20080300254A1

  公开（公告）日：2008-12-04

  Compounds of Formula I are described: preferably subject to the proviso that either (a) R 2 and R 3 together form —O—CH(R 10 )—O—, or (b) R 5 and R 6 together form —O—CH(R 10 )—O—, wherein R 10 is H, halo, or loweralkyl. Pharmaceutical salts, formulations, and methods of using the same in the treatment of cancer are also described.

  本发明描述了式I的化合物：最好是受到以下限制条件的限制，即要么（a）R2和R3共同形成—O—CH(R10)—O—，要么（b）R5和R6共同形成—O—CH(R10)—O—，其中R10是H，卤素或低碳基。还描述了药物盐、制剂和使用它们治疗癌症的方法。
• PHENANTHROINDOLIZIDINE DERIVATIVE AND NFKB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Ikeda Takashi

  公开号：US20110201637A1

  公开（公告）日：2011-08-18

  A novel compound having an excellent NFκB inhibitory effect is provided. Specifically disclosed is a compound represented by the following formula (1) or a salt thereof: wherein, R 1 represents a hydrogen atom, a lower alkyl group, or the like; R 2 represents a hydrogen atom, a lower alkyl group, a halogen atom, or the like; R 3 represents a hydrogen atom, a lower alkyl group, a hydroxyl group, or a halogen atom; R 4 represents a hydrogen atom or a lower alkyloxy group; R 5 represents a hydrogen atom, a lower alkyloxy group, a halogen atom, a hydroxyl group, or a methylenedioxy group formed together with R 6 or an isopropylidenedioxy group formed together with R 6 ; R 6 represents a hydrogen atom, a lower alkyloxy group, or a methylenedioxy group formed together with R 5 or an isopropylidenedioxy group formed together with R 5 ; R 7 represents a hydrogen atom or a lower alkyl group; and R 8 represents a hydrogen atom, a hydroxyl group, an amino group, a lower alkylcarbonyloxy group, or a halogen atom.

  提供一种具有优异的NFκB抑制效果的新化合物。具体披露的是以下式（1）或其盐的化合物：其中，R1代表氢原子，低碳基或类似物; R2代表氢原子，低碳基，卤素原子或类似物; R3代表氢原子，低碳基，羟基或卤素原子; R4代表氢原子或低碳基氧基; R5代表氢原子，低碳基氧基，卤素原子，羟基或与R6形成的亚甲二氧基或与R6形成的异丙亚甲基二氧基; R6代表氢原子，低碳基氧基或与R5形成的亚甲二氧基或与R5形成的异丙亚甲基二氧基; R7代表氢原子或低碳基; R8代表氢原子，羟基，氨基，低碳基羰基氧基或卤素原子。