15-iodo-vindoline | 847448-55-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 鸡蛋花型生物碱
• 英文名称: 15-iodo-vindoline
• 英文别名: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-4-iodo-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
• CAS: 847448-55-9
• 化学式: C₂₅H₃₁IN₂O₆
• 分子量: 582.435
• InChiKey: FCDCUQQWGBXGKT-ACSXSLCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  15-iodo-vindoline 、 苯乙炔 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 21.0h， 以67%的产率得到15-(2-phenylethynyl)vindoline
  参考文献：
  名称：

  Synthesis of C-15 Vindoline Analogues by Palladium-Catalyzed Cross-Coupling Reactions

  摘要：

  Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline with N-bromosuccinimide or N-iodosuccinimide, respectively. The study not only led to the preparation of a number of structurally novel vindoline analogues but also opens the door to new strategies for the synthesis of vinblastine, vincristine, and related anticancer agents. Also described is the conversion of ent-tabersonine to ent-vindoline.

  DOI：

  10.1021/jo061243y
• 作为产物：
  描述：

  文多灵 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以95%的产率得到15-iodo-vindoline
  参考文献：
  名称：

  文朵灵衍生物的医药用途

  摘要：

  本发明涉及一类具有如下通式I所示结构的文朵灵衍生物或其药学上可接受的盐在制备用于促进胰岛素分泌和/或预防或治疗2型糖尿病的药物中的用途，以及含有所述文朵灵衍生物或其药学上可接受的盐的用于促进胰岛素分泌和/或预防或治疗糖尿病的药物组合物。所述文朵灵衍生物对β-细胞具有促进胰岛素分泌的作用，整体动物试验表明该类化合物具有降血糖、降血脂、改善糖耐量和胰岛素耐量等功能。该类化合物可用于2型糖尿病的治疗。

  公开号：

  CN103304565B

文献信息

• Pd(II)-catalyzed cascade Heck/intramolecular C(sp)–H amidation reaction: An efficient route to 4-aryl-2-quinolinones
  作者：Chengqian Xiao、Ziyi Wang、Min Lei、Lihong Hu

  DOI：10.1016/j.tet.2016.11.075

  日期：2017.1

  A Pd(II)-catalyzed cascade Heck/intramolecular C(sp2)–H amidation reaction is described for the synthesis of 4-aryl-2-quinolinone derivatives. Substituted cinnamamide containing 2-(pyridin-2-yl)ethanamine unit reacts with aryl iodide to form intermediate by Heck reaction. Then, the intermediate takes place intramolecular amidation via C(sp2)–H activated process promoted by orientation group.

  描述了Pd（II）催化的级联Heck /分子内C（sp 2）-H酰胺化反应用于合成4-芳基-2-喹啉酮衍生物。含有2-（吡啶-2-基）乙胺单元的肉桂酰胺与芳基碘化物反应，通过Heck反应形成中间体。然后，中间体通过取向基团促进的C（sp 2）–H活化过程发生分子内酰胺化反应。
• A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl₃as the CO source
  作者：Guanglong Sun、Min Lei、Lihong Hu

  DOI：10.1039/c6ra02424f

  日期：——

  A facile and efficient method for the synthesis of alkynones by a Pd-catalyzed carbonylative Sonogashira coupling reaction starting from aryl iodide, terminal alkyne and chloroform (CHCl3) as the CO source is described. This procedure proves that CHCl3 is a cheap and efficient CO source in the presence of CsOH·H2O as the base. Furthermore, it is applied successfully for the modification of natural

  描述了一种通过Pd催化的羰基化Sonogashira偶联反应（以芳基碘化物，末端炔烃和氯仿（CHCl 3）为原料）开始合成炔烃的简便有效的方法。该程序证明，在以CsOH·H 2 O为碱的情况下，CHCl 3是一种廉价而有效的CO源。此外，它已成功地用于天然产物的修饰，如长春花碱和大黄素，从而以高收率获得了相应的产物。
• Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source
  作者：Guanglong Sun、Xue Lv、Yinan Zhang、Min Lei、Lihong Hu

  DOI：10.1021/acs.orglett.7b01882

  日期：2017.8.18

  facile and practical method for the synthesis of aromatic aldehydes by palladium-catalyzed reductive carbonylation starting from aryl iodides and HCOOH is described. Compared to the known formylation procedure, HCOOH serves not only as the most convenient and environmental-friendly C1 source but also as the reviving agent in the reductive elimination process of a Pd-catalyst. Furthermore, this procedure

  描述了一种通过钯催化从芳基碘化物和HCOOH开始的还原羰基化合成芳族醛的简便实用方法。与已知的甲酰化步骤相比，HCOOH不仅是最方便，最环保的C1来源，而且在Pd催化剂的还原消除过程中还充当了再生剂。此外，该方法也成功地应用于天然产物的修饰，如长春花碱，大黄素和长春胺，从而以高收率获得了相应的产物。
• Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source
  作者：Xue Lyu、Guanglong Sun、Yang Zhou、Yingying Wang、Min Lei、Wanying Wu、Dean Guo

  DOI：10.1007/s00706-018-2331-7

  日期：2019.2

  AbstractA practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification

  摘要已经描述了一种实用且有效的钯催化的羰基化Sonogashira交叉偶联反应，用于从芳基碘化物，炔烃和甲酸作为CO源合成炔烃。在PPh 3 / I 2的辅助下，甲酸可以用作CO来源，以中等至良好的产率合成炔酮。此外，它还成功地用于修饰天然产物，如长春花碱和大黄素，以获得相应的产物。 图形概要
• Ullmann-type C–N coupling reaction catalyzed by CuI/metformin
  作者：Chao Zhang、Zhajun Zhan、Min Lei、Lihong Hu

  DOI：10.1016/j.tet.2014.10.014

  日期：2014.11

  A facile and efficient method for Ullmann-type C-N coupling reaction of amine and aryl halide catalyzed by CuI/metformin in EtOH is described. The advantages of this method are the use of an inexpensive and readily available catalyst and ligand, easy workup, shorter reaction time, improved yields, and the use of green solvent. Furthermore, this procedure is applied successfully for the modification of natural products, such as Vindoline and Tabersonin. (C) 2014 Elsevier Ltd. All rights reserved.