2-Allyloxy-1-methyl-4-nitro-benzene | 124317-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Allyloxy-1-methyl-4-nitro-benzene
• 英文别名: 1-Methyl-4-nitro-2-[(prop-2-en-1-yl)oxy]benzene；1-methyl-4-nitro-2-prop-2-enoxybenzene
• CAS: 124317-01-7
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD27942503
• 分子量: 193.202
• InChiKey: CSVSKPNSMNFOQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Allyloxy-1-methyl-4-nitro-benzene 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 臭氧 、 一水合肼 、 丙酸 、 N,N-二乙基苯胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 78.5h， 生成
  参考文献：
  名称：

  霉酚酸的非酚吲哚类似物的合成，分子建模和评估。

  摘要：

  基于吲哚-3-甲酰胺衍生物（霉酚酸（MPA）的非酚类似物）的有前途的活性，我们在此报告了一种化合物的合成，该化合物含有两个重要的MPA活性特征：环甲氧基和甲基。合成使用两种策略完成：一种方法，该方法依赖于己烯酸酯侧链的逐步构建，然后是吲哚羧酰胺环系统，并且依赖于1,3-σ重排的收敛路径是关键步骤。对中国仓鼠和人类II型肌苷单磷酸脱氢酶（IMPDH）的对接实验表明，该化合物与NAD位点具有潜在的结合相互作用。该类似物对MCF7-S，MCF7-R或IGR-OV1癌细胞没有活性。

  DOI：

  10.1016/j.bmc.2004.03.048
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 硫酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 4.33h， 生成 2-Allyloxy-1-methyl-4-nitro-benzene
  参考文献：
  名称：

  霉酚酸的非酚吲哚类似物的合成，分子建模和评估。

  摘要：

  基于吲哚-3-甲酰胺衍生物（霉酚酸（MPA）的非酚类似物）的有前途的活性，我们在此报告了一种化合物的合成，该化合物含有两个重要的MPA活性特征：环甲氧基和甲基。合成使用两种策略完成：一种方法，该方法依赖于己烯酸酯侧链的逐步构建，然后是吲哚羧酰胺环系统，并且依赖于1,3-σ重排的收敛路径是关键步骤。对中国仓鼠和人类II型肌苷单磷酸脱氢酶（IMPDH）的对接实验表明，该化合物与NAD位点具有潜在的结合相互作用。该类似物对MCF7-S，MCF7-R或IGR-OV1癌细胞没有活性。

  DOI：

  10.1016/j.bmc.2004.03.048

文献信息

• A regioselective entry to azirino[1,2-a]indole derivatives by epoxidation/staudinger reaction of o-allylphenyl azides
  作者：Pedro Molina、Mateo Alajarín、Antonia López-Lázaro

  DOI：10.1016/s0040-4039(00)74219-5

  日期：1992.4

  On treatment with triphenylphosphine epoxy-azides 2 form azirino[1,2-a]indoles 6 via Staudinger type aminocy clization reaction.

  用三苯基膦环氧叠氮化物2处理时，会通过Staudinger型氨基连接反应形成叠氮基[1,2-a]吲哚6。
• Potential antisecretory antidiarrheals. 2. .alpha.2-Adrenergic 2-[(aryloxy)alkyl]imidazolines
  作者：Alan E. Moormann、Barnett S. Pitzele、P. H. Jones、Gary W. Gullikson、David Albin、Stella S. Yu、Robert G. Bianchi、Elizabeth L. Sanguinetti、Barbara Rubin

  DOI：10.1021/jm00164a024

  日期：1990.2

  Lofexidine, an alpha 2-agonist, has central hypotensive activity and peripheral intestinal antisecretory activity. Analogues were synthesized with increased polarity in an attempt to prevent penetration of the blood-brain barrier. The compounds were evaluated in the cholera toxin treated ligated jejunum of the rat and in the Ussing chamber with a rabbit ileum preparation. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The 2,6-dimethyl derivative of lofexidine, 4a, was as active as lofexidine in vivo, but derivatives with 2,6-substituents larger than ethyl were inactive. (Aryloxy)alkyl derivatives which have an imidazoline and a methyl or larger group as part of the alkyl exhibited the best antisecretory activity. Compounds with substituents in the para position of the phenyl ring were generally inactive. 3-Amino-2,6-dimethyl derivative 21 was twice as active as 4a. A 2-methyl substituent is required in the 3-amino series to retain good activity. 2-Methyl derivative 12a had activity comparable to that of 4a, while 6-methyl derivative 12f was inactive. Substituents on the 3-amino group did not affect the activity, but substituting a hydroxyl for the amino group produced an inactive compound. Replacing the phenyl moiety with a 4-indole resulted in retention of activity, but other heterocycles were inactive. Compound 12a was resolved and d isomer 32 was five times more potent than l isomer 33. The more active compounds in the rat cholera toxin assay (RCTA), when evaluated in the dog, exhibited antisecretory activity but also exhibited central nervous system (CNS) effects, sedation and ataxia, at 10 mg/kg, and in spontaneously hypertensive rats at 50 mg/kg. A measure of polarity, log P, was calculated for the (aryloxy)alkyl groups. Regression analysis showed no correlation of antisecretory ED50 to the calculated log P. The active compounds did not show a separation of the central CNS effects from the peripheral antisecretory activity by increasing the polarity.
• Synthesis, molecular modeling, and evaluation of nonphenolic indole analogs of mycophenolic acid
  作者：Moustafa E El-Araby、Ralph J Bernacki、Gergely M Makara、Paula J Pera、Wayne K Anderson

  DOI：10.1016/j.bmc.2004.03.048

  日期：2004.6

  Based on the promising activity of an indole-3-carboxamide derivative, a nonphenolic analog of mycophenolic acid (MPA), we report herein the synthesis of a compound containing two important features for the activity of MPA, the ring methoxy and methyl. The synthesis was accomplished using two strategies; a method dependent on stepwise building of the hexenoate side chain followed by the indolecarboxamide

  基于吲哚-3-甲酰胺衍生物（霉酚酸（MPA）的非酚类似物）的有前途的活性，我们在此报告了一种化合物的合成，该化合物含有两个重要的MPA活性特征：环甲氧基和甲基。合成使用两种策略完成：一种方法，该方法依赖于己烯酸酯侧链的逐步构建，然后是吲哚羧酰胺环系统，并且依赖于1,3-σ重排的收敛路径是关键步骤。对中国仓鼠和人类II型肌苷单磷酸脱氢酶（IMPDH）的对接实验表明，该化合物与NAD位点具有潜在的结合相互作用。该类似物对MCF7-S，MCF7-R或IGR-OV1癌细胞没有活性。