N-羟基-1-(4-异丙基苯基)甲胺 | 202471-31-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: N-羟基-1-(4-异丙基苯基)甲胺
• 英文名称: N-(4-isopropylbenzyl)hydroxylamine
• 英文别名: N-Hydroxy-1-[4-(propan-2-yl)phenyl]methanamine；N-[(4-propan-2-ylphenyl)methyl]hydroxylamine
• CAS: 202471-31-6
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: DVZBBGKDRBVXKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-羟基-1-(4-异丙基苯基)甲胺 、 2,3-dimethyl-7-[(3-methylbut-2-en-1-yl)oxy]-4-oxo-4H-chromene-8-carbaldehyde 在 PEG-400 作用下， 反应 5.0h， 以88%的产率得到(13R,17S)-4,5,14,14-tetramethyl-16-[(4-isopropylphenyl)methyl]-3,11,15-trioxa-16-azatetracyclo[8.7.0.0^2,7.0^13,17]heptadeca-1,4,7,9-tetraen-6-one
  参考文献：
  名称：

  分子内硝酮环加成反应合成新的色诺环式稠合吡喃并[4,3- c ]异恶唑衍生物及其细胞毒性评价

  摘要：

  新CI S-稠色烯并吡喃并[4,3- c ^ ]异恶唑衍生物已通过在从羟胺衍生物和7-原位生成的硝酮的分子内[1,3] -环合成ö的-prenyl衍生物8-甲酰基-2-在无催化剂的条件下，使用PEG-400作为反应介质的1,3-二取代的色农酮，收率良好。通过光谱数据建立结构，并通过X射线衍射分析进一步证实。结果表明，化合物4b，4c，4d，4e和4k对MDA-MB-231乳腺癌细胞表现出非常强的抗增殖活性。化合物4a，4c，图4e，4i和4k显示出对人MCF-7乳腺癌细胞系的有效抑制活性。化合物4H和4I展出显著抗-对人宫颈癌细胞系，HeLa细胞增殖活性。尽管4b，4d和4j对人肺癌细胞系A549具有活性。另外，发现化合物4j是最有前途的抗A549（肺癌）药物，IC 50值为0.194μM。

  DOI：

  10.1016/j.bmcl.2013.05.060
• 作为产物：
  描述：

  4-异丙基苯甲醛肟 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-羟基-1-(4-异丙基苯基)甲胺
  参考文献：
  名称：

  Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary

  摘要：

  The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to alpha-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C-2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.033

文献信息

• Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary
  作者：Masakazu Serizawa、Shuhei Fujinami、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1016/j.tetasy.2008.03.033

  日期：2008.5

  The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to alpha-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C-2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of new chromeno-annulated cis-fused pyrano[4,3-c]isoxazole derivatives via intramolecular nitrone cycloaddition and their cytotoxicity evaluation
  作者：Naveen Kumar Bejjanki、Akkaladevi Venkatesham、Jyothi Madda、Nagaiah Kommu、Sujitha Pombala、C. Ganesh Kumar、Kothakonda Rajendra Prasad、Jagadeesh Babu Nanubolu

  DOI：10.1016/j.bmcl.2013.05.060

  日期：2013.7

  New cis-fused chromeno pyrano[4,3-c]isoxazole derivatives have been synthesized by intramolecular [1,3]-cycloaddition of the nitrones generated in situ from hydroxylamine derivatives and 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones using PEG-400 as a reaction medium under catalyst-free conditions good to excellent yields. The structures were established by spectroscopic data and

  新CI S-稠色烯并吡喃并[4,3- c ^ ]异恶唑衍生物已通过在从羟胺衍生物和7-原位生成的硝酮的分子内[1,3] -环合成ö的-prenyl衍生物8-甲酰基-2-在无催化剂的条件下，使用PEG-400作为反应介质的1,3-二取代的色农酮，收率良好。通过光谱数据建立结构，并通过X射线衍射分析进一步证实。结果表明，化合物4b，4c，4d，4e和4k对MDA-MB-231乳腺癌细胞表现出非常强的抗增殖活性。化合物4a，4c，图4e，4i和4k显示出对人MCF-7乳腺癌细胞系的有效抑制活性。化合物4H和4I展出显著抗-对人宫颈癌细胞系，HeLa细胞增殖活性。尽管4b，4d和4j对人肺癌细胞系A549具有活性。另外，发现化合物4j是最有前途的抗A549（肺癌）药物，IC 50值为0.194μM。