[¹³C]-4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one | 1622398-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: [¹³C]-4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one
• 英文别名: 4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl-¹³C)-4-fluorobenzyl)phthalazin-1(2H)-one；[¹³C]-olaparib；¹³C-olaparib
• CAS: 1622398-78-0
• 化学式: C₂₄H₂₃FN₄O₃
• 分子量: 435.459
• InChiKey: FDLYAMZZIXQODN-MCHSYIMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-(3-bromo-4-fluorobenzyl)phthalazin-1(2H)-one 、 C13取代的一氧化碳 、 1-环丙甲酰基哌嗪 在 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以82%的产率得到[¹³C]-4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  Efficient Fluoride-Catalyzed Conversion of CO₂ to CO at Room Temperature

  摘要：

  A protocol for the efficient and selective reduction of carbon dioxide to carbon monoxide has been developed. Remarkably, this oxygen abstraction step can be performed with only the presence of catalytic cesium fluoride and a stoichiometric amount of a disilane in DMSO at room temperature. Rapid reduction of CO2 to CO could be achieved in only 2 h, which was observed by pressure measurements. To quantify the amount of CO produced, the reduction was coupled to an aminocarbonylation reaction using the two-chamber system, COware. The reduction was not limited to a specific disilane, since (Ph2MeSi)(2) as well as (PhMe2Si)(2) and (Me3Si)(3)SiH exhibited similar reactivity. Moreover, at a slightly elevated temperature, other fluoride salts were able to efficiently catalyze the CO2 to CO reduction. Employing a nonhygroscopic fluoride source, KHF2, omitted the need for an inert atmosphere. Substituting the disilane with silylborane, (pinacolato)BSiMe2Ph, maintained the high activity of the system, whereas the structurally related bis(pinacolato)diboron could not be activated with this fluoride methodology. Furthermore, this chemistry could be adapted to C-13-isotope labeling of six pharmaceutically relevant compounds starting from (BaCO3)-C-13 in a newly developed three-chamber system.

  DOI：

  10.1021/ja502911e

文献信息

• COtab: Expedient and Safe Setup for Pd-Catalyzed Carbonylation Chemistry
  作者：Hugo P. Collin、Wallace J. Reis、Dennis U. Nielsen、Anders T. Lindhardt、Marcelo S. Valle、Rossimiriam P. Freitas、Troels Skrydstrup

  DOI：10.1021/acs.orglett.9b01423

  日期：2019.8.2

  Bench-stable tablets (COtabs) have been developed for the rapid and safe production of carbon monoxide. The tablets can be made in less than 5 min without the use of a glovebox and only require a stock solution of an amine base to liberate a specific quantity of CO in a two-chamber system. The COtabs were tested in five different carbonylation reactions and provided similar yields compared to literature procedures. Finally, a gram-scale reaction was conducted, as well as C-13-isotope labeling of the anticancer drug, olaparib.