(Z)-3-methyl-5-(3,3-dimethyloxiran-2-yl)pent-2-enal | 96744-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-methyl-5-(3,3-dimethyloxiran-2-yl)pent-2-enal
• 英文别名: (Z)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enal；6,7-epoxyneral；(2Z)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enal
• CAS: 96744-91-1
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: VZUZJYDKCIVBDN-VURMDHGXSA-N

物化性质

• 沸点：
  243.3±13.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)
• 保留指数：
  1224

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺式-柠檬醛 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(Z)-3-methyl-5-(3,3-dimethyloxiran-2-yl)pent-2-enal
  参考文献：
  名称：

  柠檬酸和柠檬酸相关化合物对胰腺和人类B淋巴瘤细胞系活力的影响

  摘要：

  柠檬醛，3,7-二甲基-2,6-辛二烯醛，是从数种柠檬香草药中提取的精油的关键成分。它已被证明是一种有效的抗真菌剂，并且近年来在某些肿瘤细胞系中具有抗增殖作用：因此柠檬醛可能是一种潜在的抗癌药。在这项研究中，我们研究了柠檬醛对胰腺癌细胞系（MIA PaCa-2细胞）和人B淋巴瘤（DeFew细胞）增殖的影响。为了分析该分子的哪个部分对于该活性至关重要，我们还研究了几种与柠檬醛相关的化合物的作用，特别是着眼于萜类支架的某些化学方面。体外研究表明某些被测化合物具有明显的细胞毒性活性。

  DOI：

  10.1007/s00044-017-1779-z

文献信息

• Manufacture of Citronellal by the Rhodium-Catalyzed Homogeneous Hydrogenation of Neral
  作者：Jens Holz、Stephan Doerfelt、Armin Börner

  DOI：10.1002/adsc.201700941

  日期：2017.12.19

  hydrogenation of neral affording citronellal is described. The reaction has been conducted with homogeneous rhodium complexes. Among the set of ancillary diphosphane ligands tested, Xantphos was found to be superior. The relevant precatalyst has been generated from neutral metal sources such as Rh(acac)(CO)2 or the carbon monoxide‐free rhodium source Rh(acac)(cod) in the absence of any base. A high activity

  描述了提供香茅醛的神经的高度化学选择性氢化。该反应已经用均相的铑配合物进行了。在测试的一组辅助二膦配体中，Xantphos被认为是更好的。在没有任何碱的情况下，相关的前催化剂是由Rh（acac）（CO）2等中性金属源或不含一氧化碳的铑Rh（acac）（cod）源生成的。在0.1 MPa和室温下可实现高活性和化学选择性，有利于所需的香茅醛。在相同条件下，香叶菊也被还原为香茅醛。不需要像工业过程中那样向氢气流中添加一氧化碳。
• Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene
  作者：E. M. Elgendy、S. A. Khayyat

  DOI：10.1134/s1070428008060067

  日期：2008.6

  Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C-2=C-3 and C-6=C-7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C-2=C-3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.
• Nali, Micaela; Rindone, Bruno; Tollari, Stefano, Gazzetta Chimica Italiana, 1987, vol. 117, # 4, p. 207 - 212
  作者：Nali, Micaela、Rindone, Bruno、Tollari, Stefano、Valletta, Lorenzo

  DOI：——

  日期：——
• Effect of citral and citral related compounds on viability of pancreatic and human B-lymphoma cell lines
  作者：Antonia Di Mola、Antonio Massa、Vincenzo De Feo、Anna Basile、Maria Pascale、Rita Patrizia Aquino、Paolo De Caprariis

  DOI：10.1007/s00044-017-1779-z

  日期：2017.3

  Citral, 3,7-dimethyl-2,6-octadienal, is a key component of the essential oils extracted from several lemon-scented herbal plants. It has been demonstrated to be an effective antifungal agent and in recent years, to have antiproliferative effect in certain tumor cell lines: thus citral could be a potential anticancer drug. In this study, we investigated the effect of citral on the proliferation of pancreatic

  柠檬醛，3,7-二甲基-2,6-辛二烯醛，是从数种柠檬香草药中提取的精油的关键成分。它已被证明是一种有效的抗真菌剂，并且近年来在某些肿瘤细胞系中具有抗增殖作用：因此柠檬醛可能是一种潜在的抗癌药。在这项研究中，我们研究了柠檬醛对胰腺癌细胞系（MIA PaCa-2细胞）和人B淋巴瘤（DeFew细胞）增殖的影响。为了分析该分子的哪个部分对于该活性至关重要，我们还研究了几种与柠檬醛相关的化合物的作用，特别是着眼于萜类支架的某些化学方面。体外研究表明某些被测化合物具有明显的细胞毒性活性。