4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine | 79628-80-1

• 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: 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine
• 英文别名: N,N-bis(trimethylsilyl)-2-trimethylsilyloxypyrimidin-4-amine
• CAS: 79628-80-1
• 化学式: C₁₃H₂₉N₃OSi₃
• 分子量: 327.649
• InChiKey: GPBNELWLVYRDPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±52.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(氯甲氧基)十二烷 、 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine 在 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.08h， 生成 4-amino-1-dodecyloxymethyl-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Analysis of Telechelic Polyisobutylenes for Hydrogen-Bonded Supramolecular Pseudo-Block Copolymers

  摘要：

  New telechelic polyisobutylenes (PIB) with hydrogen-bonding motifs were prepared. Nucleobases such as thymine, uracil, and cytosine as well as chelate-type hydrogen-bonding donor-acceptors were affixed onto the end groups of the PIB. Starting with PIB of defined molecular weight, prepared by living cationic polymerization, hydroxyterminated PIB was generated, which subsequently was transformed into the corresponding chloromethyl ether. Reaction with silylated nucleobases furnished the final nucleobase-telechelic PIB in high yields. The chelate-type PIB was prepared by a sequence of nucleophilic/addition reaction steps adapted to the low solubility of PIB polymers in polar solvents. The structure of the PIB polymers was proven by H-1 NMR, C-13 NMR, and MALDI-TOF MS analysis proving the complete conversion between the reaction steps in quantitative yields. The pure PIB polymers with specific hydrogen bonding patterns will allow the investigation of supramolecular pseudo-block copolymers.

  DOI：

  10.1021/ma034924t
• 作为产物：
  描述：

  N,O-双三甲硅基乙酰胺 、 胞嘧啶 以 乙腈 为溶剂， 反应 0.5h， 生成 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine
  参考文献：
  名称：

  Kasnar-Samprec, Jelena; Glavas-Obrovac, Ljubica; Pavlak, Marina, Croatica Chemica Acta, 2005, vol. 78, # 2, p. 261 - 267

  摘要：

  DOI：

文献信息

• Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-.beta.-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships
  作者：Kyoichi A. Watanabe、Tsann Long Su、Robert S. Klein、Chung K. Chu、Akira Matsuda、Moon Woo Chun、Carlos Lopez、Jack J. Fox

  DOI：10.1021/jm00356a007

  日期：1983.2

  2'-"up" (arabino) configuration for enhancement of antiviral effectiveness is demonstrated by the superior activity of 2'-fluoro-5-iodo-ara-C [3a, FIAC] to that of 2'-fluoro-5-iodo-ribo-C. Of all the nucleosides tested herein, FIAC exhibited the most potent in vitro activity against HSV. 2'-Chloro-5-iodo- and -5-methyl-ara-C (3b and 4b) were 37 to greater than 500 times more effective in vitro against HSV

  描述了几种2'-卤素-5-取代-阿拉伯呋喃糖基胞嘧啶和-尿嘧啶的合成，并研究了结构与体外抗疱疹病毒活性的关系。与2'-溴类似物的2'-氯相比，那些含有2'-氟功能的阿拉伯核苷通常表现出更有效的抗疱疹病毒（HSV）活性。2'-氟-5-碘-ara-C [3a，FIAC]优于2'-氟-5-碘-ara-C [3a，FIAC]的活性证明了氟在2'-“ up”（阿拉伯糖）构型中增强抗病毒效力的重要性。 '-氟-5-碘-核糖-C。在本文测试的所有核苷中，FIAC表现出最强的抗HSV体外活性。2'
• Synthesis of racemic and enantiomerically pure 2′-thia-2′,3′-dideoxycytidine as potential anti-hepatitis B virus agents
  作者：Bai-Chuan Pan、Yung-Chi Cheng、Shih-Hsi Chu

  DOI：10.1002/jhet.5570340330

  日期：1997.5

  hetero atoms was synthesized. 2′-Thia-2′,3′-dideoxycytidine was the pilot compound of this series. (±)-β-2′-Thia-1′,3′-dideoxycytidine (6) and (±)-α-2′-thia-2′,3′-dideoxycytidine (7) were synthesized from (±)-3-mercapto-1,2-propanediol. The synthesis of the enantiomerically pure 2′-thia-2′,3′-dideoxycytidines (α-D-form, β-D-form, α-1-form and β-L-form) from optically pure (S)-(2,2-dimethyl-1,3-dioxalan-yl)methyl

  合成了一类新的具有结合到三个杂原子上的C 1原子的核苷。2'-Thia-2'，3'-二脱氧胞苷是该系列的先导化合物。由（±）-合成了（±）-β-2'-Thia-1'，3'-二脱氧胞苷（6）和（±）-α-2'-thia-2'，3'-二脱氧胞苷（7）。 3-巯基1,2-丙二醇。从光学纯的（S）-合成对映体纯的2'-thia-2'，3'-二脱氧胞苷（α-D-形式，β-D-形式，α-1-形式和β-L-形式）还描述了对甲苯磺酸（2,2-二甲基-1,3-二氧杂丙酰基）甲基（8）及其（R）-异构体18。初步生物学结果表明（+）-β-D-2'-thia-2'，3'-二脱氧胞苷（26）反对人乙型肝炎病毒中最活跃的与ED 50的3μ中号。
• A Simplified Method for the Synthesis of Pyrimidine Nucleosides
  作者：A. Matsuda、Y. Kurasawa、K. A. Watanabe

  DOI：10.1055/s-1981-29590

  日期：——
• Synthesis of 1′,2′-<i>cis</i>-Nucleoside Analogues: Evidence of Stereoelectronic Control for S_N2 Reactions at the Anomeric Center of Furanosides
  作者：Michel Prévost、Olivier St-Jean、Yvan Guindon

  DOI：10.1021/ja104429y

  日期：2010.9.8

  We are reporting a highly diastereoselective route to 1 ',2 '-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.
• Synthesis and Analysis of Telechelic Polyisobutylenes for Hydrogen-Bonded Supramolecular Pseudo-Block Copolymers
  作者：Wolfgang H. Binder、Michael J. Kunz、Christian Kluger、Getraud Hayn、Robert Saf

  DOI：10.1021/ma034924t

  日期：2004.3.1

  New telechelic polyisobutylenes (PIB) with hydrogen-bonding motifs were prepared. Nucleobases such as thymine, uracil, and cytosine as well as chelate-type hydrogen-bonding donor-acceptors were affixed onto the end groups of the PIB. Starting with PIB of defined molecular weight, prepared by living cationic polymerization, hydroxyterminated PIB was generated, which subsequently was transformed into the corresponding chloromethyl ether. Reaction with silylated nucleobases furnished the final nucleobase-telechelic PIB in high yields. The chelate-type PIB was prepared by a sequence of nucleophilic/addition reaction steps adapted to the low solubility of PIB polymers in polar solvents. The structure of the PIB polymers was proven by H-1 NMR, C-13 NMR, and MALDI-TOF MS analysis proving the complete conversion between the reaction steps in quantitative yields. The pure PIB polymers with specific hydrogen bonding patterns will allow the investigation of supramolecular pseudo-block copolymers.