ethyl 4-methyl-2-(oct-1-ynyl)-6-phenylpyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 4-methyl-2-(oct-1-ynyl)-6-phenylpyrimidine-5-carboxylate
• 英文别名: Ethyl 4-methyl-2-oct-1-ynyl-6-phenylpyrimidine-5-carboxylate；ethyl 4-methyl-2-oct-1-ynyl-6-phenylpyrimidine-5-carboxylate
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: PNDYNBJADOWTPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯	ethyl 6-methyl-4-phenylpyrimidin-2(1H)-one-5-carboxylate	69207-36-9	C14H14N2O3	258.277

反应信息

• 作为产物：
  描述：

  6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 ethyl 4-methyl-2-(oct-1-ynyl)-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  化学选择性碳-碳交叉偶联通过二硫键钯催化铜介导的CS切割

  摘要：

  AbstractAn efficient method for carbon‐carbon bond formation is described. The process employs the palladium‐catalyzed copper‐mediated cross‐coupling of diheteroaryl disulfides with arylboronic acids or alkynes to deliver CC coupling products through unreactive CS bond cleavage. The scope of the coupling reactions, including both the disulfides and arylboronic acids or alkynes, are documented.magnified image

  DOI：

  10.1002/adsc.201300776

文献信息

• Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines
  作者：Ngoc Son Le Pham、Hyunik Shin、Jun Yong Kang、Jeong-Hun Sohn

  DOI：10.1021/acs.joc.0c00091

  日期：2020.4.3

  (DHPMs) via dehydrosulfurative Sonogashira cross-coupling with concomitant oxidative dehydrogenation using a Pd/Cu catalytic system. Together with the ready availability of DHPMs possessing various substituents at the C4–C6 positions, this transformation offers rapid and general access to diverse 2-alkynylpyrimidine derivatives.

  描述了一种通过Pd / Cu催化体系通过脱硫Sonogashira交叉偶联与伴随的氧化脱氢从3,4-二氢嘧啶-1 H -2-硫酮（DHPM）一步合成2-炔基嘧啶的反应方法。连同在C4–C6位置具有各种取代基的DHPM的现成可用性，这种转变为获得各种2-炔基嘧啶衍生物提供了快速而通用的途径。
• Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines
  作者：Zheng-Jun Quan、Fu-Qiang Jing、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1002/ejoc.201300592

  日期：2013.11

  Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized

  嘧啶-2-基磺酸盐作为反应伙伴，可以从廉价的商业材料中轻松制备，并通过使用 Pd(OAc)2 催化的 Suzuki 和 Sonogashira 反应与芳基硼酸和末端炔烃有效交叉偶联。大量 C2 官能化的嘧啶已经以良好到极好的产率制备。还合成了 2-芳基吡啶和 2-(oct-1-ynyl) 吡啶。
• C–C/C–N cross-coupling reactions of aryl sulfonates catalyzed by an eco-friendly and reusable heterogeneous catalyst: wool–Pd complex
  作者：Quan-Lu Yang、Zheng-Jun Quan、Bao-Xin Du、Shang Wu、Yin-Pan Zhang、Pei-Dong Li、Ming-Ming Wang、Zi-Qiang Lei、Xi-Cun Wang

  DOI：10.1039/c5ra09765g

  日期：——

  heterogeneous palladium catalyst, supported on biomacromolecule, natural wool fibre, was found to be an effective catalyst for the C–C/C–N coupling of pyrimidin-2-yl sulfonates with arylboronic acids, terminal alkynes or anilines, giving the desired coupling products in good to high yields. The catalyst was characterized by XPS, IR, SEM and ICP. More importantly, the easy experimental handling catalyst is stable

  发现一种定义明确的多相钯催化剂，负载在生物大分子，天然羊毛纤维上，是嘧啶-2-基磺酸盐与芳基硼酸，末端炔烃或苯胺进行C-C / C-N偶联的有效催化剂，得到所需的偶联产品，具有良好的高收率。用XPS，IR，SEM和ICP对催化剂进行了表征。更重要的是，易于实验处理的催化剂是稳定的，显示出可忽略的金属浸出，并且可以重复使用至少10次连续运行。毫无疑问，对电子效应不敏感的宽范围反应物和出色的偶联收率使这些催化剂体系潜在地可用于有机合成。
• Palygorskite-anchored Pd complexes catalyze the coupling reactions of pyrimidin-2-yl sulfonates
  作者：Huiying Zhan、Rongrong Zhou、Xudong Chen、Quanlu Yang、Hongyan Jiang、Qiong Su、Yanbin Wang、Jia Li、Lan Wu、Shang Wu

  DOI：10.1039/c9ra06035a

  日期：——

  In this work, an anchored Pd complex (PGS–APTES–Pd(OAc)2) was prepared via simple and green steps from the natural clay mineral palygorskite and was well characterized by XPS, XRD, IR, SEM, and EDX. This complex was further utilized as a fine catalyst for the C–C/C–N coupling reactions of pyrimidin-2-yl sulfonates. Subsequently, the cyclic utilization test indicated the high stability and sustainability

  在这项工作中，通过简单的绿色步骤从天然粘土矿物坡缕石制备锚定 Pd 配合物 (PGS-APTES-Pd(OAc) 2 )，并通过 XPS、XRD、IR、SEM 和 EDX 对其进行了很好的表征。该配合物进一步用作嘧啶-2-基磺酸盐的 C-C/C-N 偶联反应的精细催化剂。随后，循环利用试验表明该PGS-APTES-Pd(OAc) 2催化剂具有较高的稳定性和可持续性，并且在回收过程中无需活化，为有机合成提供了一种适用且可重复使用的催化剂。
• Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions
  作者：Quanlu Yang、Zhengjun Quan、Baoxin Du、Shang Wu、Peidong Li、Yanxia Sun、Ziqiang Lei、Xicun Wang

  DOI：10.1039/c5cy00802f

  日期：——

  A biomacromolecule-anchored palladium complex, wool-Pd(OAc)₂, was used as a catalyst for the Liebeskind–Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and arylboronic acids.

  一种生物大分子锚定的钯配合物，羊毛-Pd(OAc)₂，被用作催化剂，用于Liebeskind–Srogl去硫偶联反应，将嘧啶基硫醚衍生物与末端炔烃和芳基硼酸进行偶联。