(E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile | 94326-16-6

• 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
• 英文名称: (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile
• 英文别名: β-Ionolacetonitril
• CAS: 94326-16-6
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: UWQFTCQNMKWWMP-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以8%的产率得到
  参考文献：
  名称：

  Azetidinone–retinoid hybrids: Synthesis and differentiative effects

  摘要：

  As a part of a systematic investigation on the synthesis and biological activities of new B-lactam compounds, we examined beta-lactam candidates 1, 2E and 2Z and their ability to induce cell proliferation or differentiation. Azetidinone 1 was chosen for its activity (previously evaluated) as selective HDAC8 inhibitor, whereas beta-lactams 2E and 2Z were designed to have a hybrid retinoid-azetidinone structure, de nova synthesized and fully characterized. Biological activities were determined in cellular assays on neuroblastoma cells SH-SY5Y. Azetidinone 1, 2E and 2Z led to a moderate effect in decreasing SH-SY5Y cell proliferation and beta-lactams 2E and 2Z induced an early stage differentiation.The present results uncovered a new role of specifically designed beta-lactam compounds in epigenetic regulation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.057
• 作为产物：
  描述：

  beta-紫罗酮 、 乙腈 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以85%的产率得到(E)-3-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-4-enenitrile
  参考文献：
  名称：

  Azetidinone–retinoid hybrids: Synthesis and differentiative effects

  摘要：

  As a part of a systematic investigation on the synthesis and biological activities of new B-lactam compounds, we examined beta-lactam candidates 1, 2E and 2Z and their ability to induce cell proliferation or differentiation. Azetidinone 1 was chosen for its activity (previously evaluated) as selective HDAC8 inhibitor, whereas beta-lactams 2E and 2Z were designed to have a hybrid retinoid-azetidinone structure, de nova synthesized and fully characterized. Biological activities were determined in cellular assays on neuroblastoma cells SH-SY5Y. Azetidinone 1, 2E and 2Z led to a moderate effect in decreasing SH-SY5Y cell proliferation and beta-lactams 2E and 2Z induced an early stage differentiation.The present results uncovered a new role of specifically designed beta-lactam compounds in epigenetic regulation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.057

文献信息

• Ruthenium-catalyzed formation of pyrazoles or 3-hydroxynitriles from propargyl alcohols and hydrazines
  作者：Julia Kaufmann、Elisabeth Jäckel、Edgar Haak

  DOI：10.24820/ark.5550190.p010.893

  日期：——

  Functionalized pyrazoles are generated from secondary propragyl alcohols and hydrazines in a rutheniumcatalyzed cascade process, consisting of redox isomerization, Michael addition, cyclocondensation and dehydrogenation steps. The same bifunctional catalyst mediates the conversion of tertiary propargyl alcohols with hydrazine to 3-hydroxynitriles via anti-Markovnikov hydroamination followed by elimination

  官能化吡唑是在钌催化的级联过程中由仲丙醇和肼生成的，包括氧化还原异构化、迈克尔加成、环缩合和脱氢步骤。相同的双功能催化剂通过反马尔可夫尼科夫加氢胺化随后消除氨来介导炔丙醇叔醇与肼的转化为 3-羟基腈。