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| 211811-09-5

中文名称
——
中文别名
——
英文名称
——
英文别名
——
化学式
CAS
211811-09-5
化学式
C17H13ClF2N4O3
mdl
——
分子量
394.765
InChiKey
FZSXZFARNIPSEG-BZNIZROVSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.26
  • 重原子数:
    27.0
  • 可旋转键数:
    4.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    79.13
  • 氢给体数:
    0.0
  • 氢受体数:
    7.0

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    作用下, 反应 28.0h, 以66%的产率得到[(2R,5S)-5-(6-aminopurin-9-yl)-4,4-difluoro-tetrahydrofuran-2-yl]methanol
    参考文献:
    名称:
    Synthesis of 2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranosyl nucleosides
    摘要:
    Various 2,3-dideoxy-2,2-difluoro-L-glycero-pentofuranosyl nucleosides were synthesized via the key intermediate, 5-O-benzoyl-2,3-dideoxy-2,2-difluoro-L-glycero-pentofuranose (6). 2,3-O-Isopropylidene-L-glyceraldehyde was coupled with ethyl bromodifluoroacetate under Reformatsky conditions to obtain the diastereomeric mixture of ethyl (4S)-3-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (1). Treatment of compound 1 with carbon disulfide, sodium hydride and methyl iodide followed by reduction afforded ethyl (4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (3). Compound 3 was treated with 5% HCl in ethanol, followed by refluxing in benzene under Dean-Stark conditions, to afford the lactone 4. The compound 4 was protected and reduced to afford the key intermediate 6. For the synthesis of pyrimidine derivatives 8-21, compound 6 was converted to the mesylate 7 and condensed with various silyl protected pyrimidine bases. The inosine and adenine derivatives 38-41 were obtained from compound 6 and 6-chloropurine using standard procedures. Compounds 22-35 and 38-41 were evaluated for their antiviral activity against HIV-1, HBV, HSV-1 and HSV-2, and for cellular toxicity. None of the synthesized compounds showed any significant activity or toxicity. Single-crystal X-ray structure of 1-(2,3-dideoxy-2,2-difluoro-beta-L-glycero-pentofuranosyl)-5-iodocytosine (34) suggested a 2'-exo/3'-endo conformation for the carbohydrate moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0008-6215(97)00275-9
  • 作为产物:
    参考文献:
    名称:
    Synthesis of 2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranosyl nucleosides
    摘要:
    Various 2,3-dideoxy-2,2-difluoro-L-glycero-pentofuranosyl nucleosides were synthesized via the key intermediate, 5-O-benzoyl-2,3-dideoxy-2,2-difluoro-L-glycero-pentofuranose (6). 2,3-O-Isopropylidene-L-glyceraldehyde was coupled with ethyl bromodifluoroacetate under Reformatsky conditions to obtain the diastereomeric mixture of ethyl (4S)-3-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (1). Treatment of compound 1 with carbon disulfide, sodium hydride and methyl iodide followed by reduction afforded ethyl (4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro propionate (3). Compound 3 was treated with 5% HCl in ethanol, followed by refluxing in benzene under Dean-Stark conditions, to afford the lactone 4. The compound 4 was protected and reduced to afford the key intermediate 6. For the synthesis of pyrimidine derivatives 8-21, compound 6 was converted to the mesylate 7 and condensed with various silyl protected pyrimidine bases. The inosine and adenine derivatives 38-41 were obtained from compound 6 and 6-chloropurine using standard procedures. Compounds 22-35 and 38-41 were evaluated for their antiviral activity against HIV-1, HBV, HSV-1 and HSV-2, and for cellular toxicity. None of the synthesized compounds showed any significant activity or toxicity. Single-crystal X-ray structure of 1-(2,3-dideoxy-2,2-difluoro-beta-L-glycero-pentofuranosyl)-5-iodocytosine (34) suggested a 2'-exo/3'-endo conformation for the carbohydrate moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0008-6215(97)00275-9
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同类化合物

齐夫多定相关物质B 齐多夫定 黄质核苷 黄苷5'-(四氢三磷酸酯)三钠盐 黄苷3',5'-环单磷酸酯 黄苷-5'-三磷酸酯 黄嘌呤核苷 鸟苷酸 鸟苷酰-3'-5'-胞苷铵盐 鸟苷酰-(3'-5')-尿苷 鸟苷酰-(3'-5')-3'-鸟苷酸 鸟苷酰(3'-5')尿苷3'-单磷酸酯 鸟苷三磷酸锂 鸟苷5'-硫代二磷酸酯 鸟苷5'-三磷酸酯锰盐 鸟苷5'-[氢(膦酰甲基)膦酸酯]钠盐 鸟苷3'-(三氢二磷酸酯),5'-(三氢二磷酸酯) 鸟苷2’,3’-环单磷酸酯三乙胺盐 鸟苷-5’-二磷酸 鸟苷-5'-三磷酸二钠盐 鸟苷-5'-O-(2-硫代三磷酸)三锂盐 鸟苷-3,5-环单磷酸单钠盐 鸟苷-3',5'-环单硫代磷酸酯 Rp-异构体钠盐 鸟苷,N,N-二甲基-6-O-[2-(4-硝基苯基)乙基]- 鸟苷(5')四磷酰(5')鸟苷 鸟苷 5'-(四氢三磷酸酯-P''-32P) 鸟苷 5'-(四氢 5-硫代三磷酸酯) 鸟苷 2',3',5'-三苯甲酸酯 鸟苷 鸟氨酸,乙基酯(9CI) 鸟嘌呤核糖苷-3’,5’-环磷酸酯 鲁西他滨 马来酸恩替卡韦 马兜铃内酰胺A 顺式5-氟-1-[2-(羟甲基)-1,3-氧硫杂环戊-5-基]-2,4(1H,3H)-嘧啶二酮-13C,15N2 顺式5-氟-1-[2-(羟甲基)-1,3-氧硫杂环戊-5-基]-2,4(1H,3H)-嘧啶二酮 顺式-玉米素-D-核糖甙 顺-5-氟-1-[2-[[[[(((1,1-二甲基乙基)二甲基甲硅烷基]氧基]甲基]-1,3-氧杂硫杂环戊-5-基]-2,4(1H,3H)-嘧啶二酮-13C,15N2 顺-5-氟-1-[2-[[[[(((1,1-二甲基乙基)二甲基甲硅烷基]氧基]甲基]-1,3-氧杂硫杂环戊-5-基]-2,4(1H,3H)-嘧啶二酮 非阿尿苷5’-单磷酸酯 非阿尿苷 非西他滨 阿糖腺苷2',3',5'-三乙酸酯 阿糖腺苷 2',3'-二乙酸酯 阿糖腺苷 阿糖腺苷 阿糖胞苷杂质6 阿糖胞苷杂质19 阿糖胞苷杂质17 阿糖胞苷杂质13