tert-butyl (tert-butoxycarbonyl)(5-iodopyrimidin-2-yl)carbamate | 1361537-47-4

• 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: tert-butyl (tert-butoxycarbonyl)(5-iodopyrimidin-2-yl)carbamate
• 英文别名: N,N-Di-(tert-butoxycarbonyl)-5-iodopyrimidin-2-amine；tert-butyl N-(5-iodopyrimidin-2-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1361537-47-4
• 化学式: C₁₄H₂₀IN₃O₄
• 分子量: 421.235
• InChiKey: JNGAFDIRARQTBW-UHFFFAOYSA-N

物化性质

• 沸点：
  433.4±37.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (tert-butoxycarbonyl)(5-iodopyrimidin-2-yl)carbamate 在 copper(l) iodide 、 1,10-菲罗啉 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

  摘要：

  We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

  DOI：

  10.1021/jm401625b
• 作为产物：
  描述：

  2-氨基-5-碘嘧啶, 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到tert-butyl (tert-butoxycarbonyl)(5-iodopyrimidin-2-yl)carbamate
  参考文献：
  名称：

  氨基嘧啶和环状胍氨基酸的不对称合成

  摘要：

  描述了具有氨基嘧啶和环状胍侧链的氨基酸的合成。合成路线采用2-乙酰氨基丙烯酸甲酯与4-甲氧基苄基保护的2-氨基-5-碘嘧啶的Heck偶联，然后由Rh（I）催化的不对称氢化，得到手性保护的氨基酸。在酸性条件下除去所有保护基以提供氨基酸（S）-2-氨基-3-（2-氨基嘧啶-5-基）丙酸，将其氢化以提供具有六元环的氨基酸胍侧链。

  DOI：

  10.1016/j.tetlet.2013.06.066

文献信息

• 2-Aminopyrimidine as a novel scaffold for biofilm modulation
  作者：Erick A. Lindsey、Roberta J. Worthington、Cristina Alcaraz、Christian Melander

  DOI：10.1039/c2ob06871k

  日期：——

  An efficient synthetic route to a series of substituted 2-aminopyrimidine (2-AP) derivatives has been developed. Subsequent biofilm screening has allowed comparison between the biological activity of these new derivatives and that of the 2-aminoimidazole class of anti-biofilm compounds. Several derivatives displayed the ability to modulate bacterial biofilm formation, exhibiting greater activity against Gram-positive strains than Gram-negative strains. Additionally some 2-aminopyrmidines were able to suppress MRSA resistance to conventional antibiotics.

  我们开发出了一系列取代的 2-氨基嘧啶（2-AP）衍生物的高效合成路线。随后的生物膜筛选将这些新衍生物的生物活性与 2-氨基咪唑类抗生物膜化合物的生物活性进行了比较。一些衍生物显示出调节细菌生物膜形成的能力，对革兰氏阳性菌株的活性高于对革兰氏阴性菌株的活性。此外，一些 2-aminopyrmidines 还能抑制 MRSA 对传统抗生素的耐药性。
• Photoredox-Mediated, Nickel-Catalyzed Trifluoromethylthiolation of Aryl and Heteroaryl Iodides
  作者：Christopher S. Gravatt、Jeffrey W. Johannes、Eric R. King、Avipsa Ghosh

  DOI：10.1021/acs.joc.2c00631

  日期：2022.7.15

  While trifluoromethylthiolation of aryl halides has been extensively explored, the current methods require complex and/or air-sensitive catalysts. Reported here is a method employing a bench-stable Ni(II) salt and an iridium photocatalyst that can mediate the trifluoromethylthiolation of a wide range of electronically diverse aryl and heteroaryl iodides, likely via a Ni(I)/Ni(III) catalytic cycle.

  虽然已经广泛探索了芳基卤化物的三氟甲基硫醇化，但目前的方法需要复杂的和/或空气敏感的催化剂。本文报道了一种使用台式 Ni(II) 盐和铱光催化剂的方法，该方法可以介导各种电子多样化芳基和杂芳基碘化物的三氟甲基硫醇化，可能通过 Ni(I)/Ni(III) 催化循环. 该反应具有广泛的官能团耐受性和在药物化学中的应用潜力，如获得（外消旋）-莫奈太尔的后期功能化方法所证明的那样。