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9-苄基-2,6-二氯-9h-嘌呤 | 79064-26-9

中文名称
9-苄基-2,6-二氯-9h-嘌呤
中文别名
——
英文名称
9-benzyl-2,6-dichloro-9H-purine
英文别名
9-benzyl-2,6-dichloropurine
9-苄基-2,6-二氯-9h-嘌呤化学式
CAS
79064-26-9
化学式
C12H8Cl2N4
mdl
——
分子量
279.128
InChiKey
CUYCHULDTCBWLI-UHFFFAOYSA-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

物化性质

  • 熔点:
    136-138 °C
  • 沸点:
    430.5±55.0 °C(Predicted)
  • 密度:
    1.51±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    4
  • 重原子数:
    18
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.08
  • 拓扑面积:
    43.6
  • 氢给体数:
    0
  • 氢受体数:
    3

安全信息

  • 海关编码:
    2933990090
  • 危险性防范说明:
    P261,P305+P351+P338
  • 危险性描述:
    H302,H315,H319,H335
  • 储存条件:
    2-8°C

SDS

SDS:919f1777ed8e32d5dae0ae5758584012
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
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反应信息

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文献信息

  • Regiochemistry in Stille couplings of 2,6-dihalopurines
    作者:Geir Langli、Lise-Lotte Gundersen、Frode Rise
    DOI:10.1016/0040-4020(96)00199-8
    日期:1996.4
    The regiochemistry in Stille couplings of 2,6-dihalopurines have been studied. 2,6-Dichloropurines react selectively in the 6-position, and 6-chloro-2-iodopurines and 2-bromo-6-chloropurines in the 2-position.
    已经研究了2,6-二卤代尿烷在Stille偶联中的区域化学2,6-二氯嘌呤在6-位选择性反应,6--2-碘嘌呤和2--6-氯嘌呤在2-位选择性反应。
  • The Suzuki-Miyaura Cross-Coupling Reactionsof 2-, 6- or 8-Halopurines with Boronic Acids Leading to 2-, 6- or 8-Aryl- and -Alkenylpurine Derivatives
    作者:Martina Havelková、Dalimil Dvořak、Michal Hocek
    DOI:10.1055/s-2001-16765
    日期:——
    The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine, 9- or 3-benzyl-8-bromoadenine and 2,6-dihalopurines with boronic acids gave the corresponding 6-, 8- or 2-aryl- or -alkenylpurines in good yields. Anhydrous conditions in toluene were superior for coupling of electron-rich boronic acids, while aqueous DME was used for electron-poor arylboronic acids as well as for alkenylboronic acids. A good regioselectivity was observed for the coupling of 2,6-dihalopurines: 9-benzyl-2,6-dichloropurine reacted with one equivalent of phenyl boronic acid to give 9-benzyl-2-chloro-6-phenylpurine, while an analogous reaction of 9-benzyl-6-chloro-2-iodopurine gave selectively 9-benzyl-6-chloro-2-phenylpurine.
    9-苄基-6-氯嘌呤、9-或3-苄基-8-溴腺嘌呤及2,6-二卤嘌呤硼酸进行的铃木-宫浦交叉偶联反应,以良好产率得到了相应的6-、8-或2-芳基或烯基嘌呤生物。无条件下以甲苯为溶剂对于富电子硼酸的偶联反应较为有利,而贫电子芳基硼酸及烯基硼酸则以含二甲氧基乙烷(DME)为溶剂进行反应。在2,6-二卤嘌呤的偶联反应中可以观察到良好的区域选择性:9-苄基-2,6-二氯嘌呤与一当量苯硼酸反应得到了9-苄基-2--6-苯基嘌呤,而9-苄基-6-氯-2-碘嘌呤的类似反应则高选择性地得到了9-苄基-6--2-苯基嘌呤
  • Design and synthesis of a new generation of substituted purine hydroxamate analogs as histone deacetylase inhibitors
    作者:Renshuai Liu、Junhua Wang、Weiping Tang、Hao Fang
    DOI:10.1016/j.bmc.2016.02.005
    日期:2016.4
    Histone deacetylase inhibitors have been proved to be great potential for the treatment of cancer. Recently, we designed and modified a series of substituted purine hydroxamate analogs as potent HDAC inhibitors based on our previous studies. The target compounds were investigated for their in vitro HDAC inhibitory activities and anti-proliferative activities. Results indicated that these compounds
    组蛋白脱乙酰基酶抑制剂已被证明在治疗癌症方面具有巨大潜力。最近,我们根据先前的研究设计并修饰了一系列取代的嘌呤异羟酯类似物,作为有效的HDAC抑制剂。研究了目标化合物的体外HDAC抑制活性和抗增殖活性。结果表明,这些化合物可有效抑制HDAC,对肿瘤细胞具有明显的抗增殖活性。可能地,目标化合物4m和4n在酶抑制活性和细胞抗增殖活性测定方面均优于SAHA。
  • Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ
    作者:Ashraf Brik、Chung-Yi Wu、Michael D. Best、Chi-Huey Wong
    DOI:10.1016/j.bmc.2005.02.066
    日期:2005.8
    been invested in the synthesis of purine libraries due to their importance in targeting various enzymes involved in different diseases and cellular processes. The synthesis of N9-alkylated purine scaffolds relied mostly on Mitsunobu conditions with a variety of alcohols or strong basic conditions with different organic halides. A more reliable and efficient way for the synthesis of N(9)-alkylated purine
    由于嘌呤文库对于靶向涉及不同疾病和细胞过程的各种酶具有重要意义,因此已在嘌呤文库的合成方面投入了大量精力。N9-烷基化嘌呤支架的合成主要依赖于Mitsunobu条件下的各种醇类或强碱性条件下的不同有机卤化物。报道了一种更可靠和有效的合成N(9)-烷基化嘌呤支架的方法。该方法使用化四丁基(TBAF)来辅助这种化学反应。在许多情况下,反应在10分钟内完成,并以高收率和选择性提供了所需的产物。此外,这些温和的反应条件使其可用于微量滴定板的组合反应,然后进行原位筛选以发现有效的磺基转移酶抑制剂
  • Synthesis and bronchodilating activity of 2,9-disubstituted adenine derivatives: BB-1502 (9-cyclohexy-2-n-propoxy-9H-adenine) and its analogs.
    作者:TAKAYUKI NAITO、SUSUMU NAKAGAWA、TAKAAKI OKITA、HARUHIRO YAMASHITA、TETSURO YAMASAKI、HIDEO KAMEI、KOZO TOMATSU、HIDEYO IMANISHI、HIROSHI KAWAGUCHI
    DOI:10.1248/cpb.30.2011
    日期:——
    A series of 2, 9-disubstituted adenine derivatives was prepared and evaluated for bronchodilating activity. 9-(2-Cyclohexenyl), 9-tetrahydropyranyl and 9-benzyl derivatives of 2, 6-dichloropurine were converted to the 2-chloroadenines. Subsequent nucleophilic substitution of the 2-chloro group with alkoxides, mercaptides and amines afforded the desired compounds. 9-Cyclohexyl derivatives were prepared by hydrogenation of the corresponding 9-cyclohexenyl compounds. Bronchodilating activities of the new adenine derivatives were evaluated in a number of biological systems. 9-(2-Cyclohexenyl)- and 9-cyclohexyladenines having an ethoxy, n-propoxy, n-butoxy or n-propylthio group at the 2-position showed potent bronchodilating activity. Reduced activity was observed with lower or higher alkoxy homologs and branched alkoxy congeners. 9-Cyclohexyl-2-n-propoxy-9H-adenine (designated as BB-1502) was selected for further studies in view of its high intrinsic activity and favorable pharmacological profile.
    一系列2,9-二取代的腺苷生物被制备并评估其支气管扩张活性。9-(2-环己烯基)、9-四氢吡喃基和9-苄基的2,6-二氯嘌呤生物被转化为2-腺嘌呤。随后用醇盐、硫醇盐和胺对2-基团进行亲核取代,得到目标化合物。通过还原相应的9-环己烯基化合物制备9-环己基衍生物。这些新的腺苷生物的支气管扩张活性在一系列生物系统中进行了评估。在2位具有乙氧基、正丙氧基、正丁氧基或正丙硫基的9-(2-环己烯基)-和9-环己基腺嘌呤显示出强效的支气管扩张活性。较低或较高的醇氧同系物以及支链醇氧类似物的活性降低。9-环己基-2-正丙氧基-9H-腺嘌呤(标记为BB-1502)因其高内在活性和良好的药理学特性被选中进行进一步研究。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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