tert-butyl 3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propylcarbamate

• 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 3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propylcarbamate
• 英文别名: tert-butyl (3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propyl)carbamate；t-butyl 3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propylcarbamate；1-(3-N-tert-butoxycarbonylaminopropyl)-5-methyl-1H-pyrimidine-2,4-dione；tert-butyl N-[3-(5-methyl-2,4-dioxopyrimidin-1-yl)propyl]carbamate
• 化学式: C₁₃H₂₁N₃O₄
• 分子量: 283.327
• InChiKey: WMPJSZFXIQXUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以98%的产率得到1-(3-amino-propyl)-5-methyl-1H-pyrimidine-2,4-dione trifluoroacetate
  参考文献：
  名称：

  Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues

  摘要：

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.

  DOI：

  10.1080/15257770902736467
• 作为产物：
  描述：

  N-Boc-3-氨基丙基溴 、 胸腺嘧啶 在 potassium carbonate 作用下， 以 正己烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propylcarbamate
  参考文献：
  名称：

  Pyrimidinedione derivatives useful as alpha 1A adrenoceptor antagonists

  摘要：

  揭示了新型嘧啶二酮类化合物及其药用盐。还描述了这些化合物的合成以及它们作为α1a肾上腺素受体拮抗剂的用途。这些化合物的一个应用是用于治疗良性前列腺增生。这些化合物在选择性上能够放松富含α1a受体亚型的平滑肌组织，同时不引起低血压。这样的组织包括尿道内膜周围的组织。因此，这些化合物的一个用途是为患有良性前列腺增生的男性提供急性缓解，从而减少尿液流动的阻碍。这些化合物的另一个用途是与人类5α-还原酶抑制剂化合物结合，以实现对良性前列腺增生影响的急性和慢性缓解。

  公开号：

  US06232318B1

文献信息

• Rapid access with diversity to enantiopure flexible PNA monomers following asymmetric orthogonal strategies
  作者：Carlos T. Nieto、Mateo M. Salgado、Sara H. Domínguez、David Díez、Narciso M. Garrido

  DOI：10.1016/j.tetasy.2014.06.002

  日期：2014.7

  Different synthetic procedures are described in the rapid elaboration of flexible PNA monomers based on the 6-amino-8-base-octanoate and 5-amino-7-base-heptanoate scaffolds. Asymmetric Aza-Michael monoaddition is successfully applied to starting materials derived from sebacic/azelaic long-chain diacids and 6-membered oxacyclohexane commercial derivatives. Chain length, orthogonality of the ester functionalities

  不同的合成方法以基于6-氨基-8-基辛酸酯和5-氨基-7-基庚支架柔性PNA单体的快速阐述的描述。不对称氮杂-迈克尔单加成被成功地应用到开始从癸二/壬二酸长链二元酸和6-元oxacyclohexane商业衍生物衍生的材料。链长，酯官能团的正交性，并且ž / ë这些素底物的异构通过这个不对称共轭加成，得到高有价值的多官能的中间体。关键特征是PNA单体合成，正交化学选择性转化和Mitsunobu核碱基取代的多样性，这是在最终步骤中引入核碱基的一种特殊方法。
• Boncel; Walczak, Polish Journal of Chemistry, 2007, vol. 81, # 12, p. 2151 - 2156
  作者：Boncel、Walczak

  DOI：——

  日期：——
• US6232318B1
  申请人：——

  公开号：US6232318B1

  公开（公告）日：2001-05-15
• [EN] PYRIMIDINEDIONE DERIVATIVES USEFUL AS ALPHA 1A ADRENOCEPTOR ANTAGONISTS<br/>[FR] DERIVES DE LA PYRIMIDINEDIONE, ANTAGONISTES DE L'ADRENOCEPTEUR ALPHA 1A
  申请人：MERCK & CO INC

  公开号：WO2000029386A1

  公开（公告）日：2000-05-25

  Novel pyrimidinedione compounds and pharmaceutically acceptable salts thereof are disclosed. The synthesis of these compounds and their use as alpha 1a adrenergic receptor antagonists is also described. One application of these compounds is in the treatment of benign prostatic hyperplasia. These compounds are selective in their ability to relax smooth muscle tissue enriched in the alpha 1a receptor subtype without at the same time inducing hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia can be achieved.
• Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues
  作者：Slawomir Boncel、Krzysztof Walczak

  DOI：10.1080/15257770902736467

  日期：2009.3.11

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.