1H-吡唑-4-甲醛,5-氯-3-(1-甲基乙基)-1-苯基- | 139347-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1H-吡唑-4-甲醛,5-氯-3-(1-甲基乙基)-1-苯基-
• 英文名称: 5-chloro-3-isopropyl-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-chloro-1-phenyl-3-propan-2-ylpyrazole-4-carbaldehyde
• CAS: 139347-65-2
• 化学式: C₁₃H₁₃ClN₂O
• mdl: MFCD00186376
• 分子量: 248.712
• InChiKey: OSPKUZNNNGNAAC-UHFFFAOYSA-N

物化性质

• 沸点：
  366.0±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-吡唑-4-甲醛,5-氯-3-(1-甲基乙基)-1-苯基- 在 sodium azide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 8.0h， 生成 4-Cyano-5-hydroxy-3-isopropyl-1-phenylpyrazole
  参考文献：
  名称：

  Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

  摘要：

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.

  DOI：

  10.1021/jo00033a039
• 作为产物：
  描述：

  3-异丙基-1-苯基-1H-吡唑-5(4h)-酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 0.33h， 以29.86%的产率得到1H-吡唑-4-甲醛,5-氯-3-(1-甲基乙基)-1-苯基-
  参考文献：
  名称：

  Selenopyrano[2,3-c]pyrazol-4(1H)-ones的合成及其CH活化

  摘要：

  在此，我们首次公开了通过原位生成的硒化物直接与 α-卤代反应形成硒-吡喃环来合成硒基吡喃并 [2,3-c] 吡唑-4(1H)-酮及其芳基衍生物。带有取代吡唑的β-炔酮提供伴随的硒吡喃并[2,3-c]吡唑-4(1H)-酮。随后由钯催化的 Heck 反应影响的后续化合物的直接 C-H 芳基化能够在硒吡喃并 [2,3-c] 吡唑-4(1H)-酮支架上以中等至良好的产率掺入芳烃取代基，这可能是有用的用于生物筛查。

  DOI：

  10.1055/a-1296-8835

文献信息

• Identification of antitumor activity of pyrazole oxime ethers
  作者：Hyun-Ja Park、Kyung Lee、Su-Jin Park、Bangle Ahn、Jong-Cheol Lee、HeeYeong Cho、Kee-In Lee

  DOI：10.1016/j.bmcl.2005.03.082

  日期：2005.7

  A series of pyrazole oxime ether derivatives were prepared and examined as cytotoxic agents. In particular, 5-phenoxypyrazole was comparable to doxorubicin, while exhibiting very potent cytotoxicity against XF 498 and HCT15. (c) 2005 Elsevier Ltd. All rights reserved.
• Nivorozhkin, A. L.; Korobov, M. S.; Konstantinovskii, L. E., Journal of general chemistry of the USSR, 1985, vol. 55, # 4, p. 757 - 768
  作者：Nivorozhkin, A. L.、Korobov, M. S.、Konstantinovskii, L. E.、Nivorozhkin, L. E.、Minkin, V. I.

  DOI：——

  日期：——
• Synthesis of Selenopyrano[2,3-c]pyrazol-4(1H)-ones and Their C–H Activation
  作者：Hitesh B. Jalani、Jin-Hyun Jeong、In-Hui Choi

  DOI：10.1055/a-1296-8835

  日期：2021.2

  3-c]pyrazol-4(1H)-ones and their aryl derivatives for the first time using seleno-pyran ring formation via an in situ generated selenide reacting directly with α-halo-β-ynones bearing substituted pyrazoles to provide concomitant selenopyrano[2,3-c]pyrazol-4(1H)-ones. Subsequent direct C–H arylation of the later compounds effected by palladium catalyzed Heck reaction enables the incorporation of arene

  在此，我们首次公开了通过原位生成的硒化物直接与 α-卤代反应形成硒-吡喃环来合成硒基吡喃并 [2,3-c] 吡唑-4(1H)-酮及其芳基衍生物。带有取代吡唑的β-炔酮提供伴随的硒吡喃并[2,3-c]吡唑-4(1H)-酮。随后由钯催化的 Heck 反应影响的后续化合物的直接 C-H 芳基化能够在硒吡喃并 [2,3-c] 吡唑-4(1H)-酮支架上以中等至良好的产率掺入芳烃取代基，这可能是有用的用于生物筛查。
• Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes
  作者：Jan Becher、Per Lauge Joergensen、Krystian Pluta、Niels J. Krake、Birgitte Falt-Hansen

  DOI：10.1021/jo00033a039

  日期：1992.3

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.