2-[(2,6-二甲基苯氧基)甲基]环氧乙烷 | 5296-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[(2,6-二甲基苯氧基)甲基]环氧乙烷
• 英文名称: 2,6-dimethylphenyl glycidyl ether
• 英文别名: (+/-)-1,2-epoxy-3-(2,6-dimethylphenoxy)propane；1,2-epoxy-3-(2,6-dimethylphenoxy)propane；2-((2,6-dimethylphenoxy)methyl)oxirane；(2,6-dimethyl-phenoxymethyl)-oxirane；2-(2,3-epoxy-propoxy)-m-xylene；2-(2,3-Epoxy-propoxy)-m-xylol；2-[(2,6-Dimethylphenoxy)methyl]oxirane
• CAS: 5296-34-4
• 化学式: C₁₁H₁₄O₂
• mdl: MFCD02171144
• 分子量: 178.231
• InChiKey: VHWHISLSSKROOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  2-[(2,6-二甲基苯氧基)甲基]环氧乙烷 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 28.5h， 生成 3-[3-(2,6-Dimethyl-phenoxy)-2-hydroxy-propylamino]-propionic acid ethyl ester; hydrochloride
  参考文献：
  名称：

  超短效β-肾上腺素受体阻断剂。1.在氮取代基中包含酯的（芳氧基）丙醇胺。

  摘要：

  为了产生短效的β-肾上腺素受体阻断剂，我们制备了几种具有酯官能团的（芳氧基）丙醇胺并入氮取代基。这些化合物中的许多在连续静脉输注40分钟后显示出很短的阻断活性。然而，发现它们的持续时间随着更长的静脉内输注而显着增加。

  DOI：

  10.1021/jm00354a002
• 作为产物：
  描述：

  1-chloro-3-(2,6-dimethyl-phenoxy)-propan-2-ol 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 2-[(2,6-二甲基苯氧基)甲基]环氧乙烷
  参考文献：
  名称：

  Antihypertensive indole derivatives of phenoxypropanolamines with .beta.-adrenergic receptor antagonist and vasodilating activity

  摘要：

  A series of 25 aryloxypropanolamines containing the 3-indolyl-tert-butyl [i.e., 1,1-dimethyl-2-(1H-indol-3-yl)ethyl] or substituted 3-indolyl-tert-butyl moiety as the N substituent is reported. These compounds have been tested for antihypertensive activity in spontaneously hypertensive rats (SHR), beta-adrenergic receptor antagonist action in conscious normotensive rats, vasodilating activity in ganglion-blocked rats with blood pressure maintained by angiotensin II infusion, and for intrinsic sympathomimetic action (ISA) in reserpinized rats. Some of the compounds exhibit antihypertensive activity in combination with beta adrenergic receptor antagonist and vasodilating action. The structure--activity relationships in these tests are discussed.

  DOI：

  10.1021/jm00177a015

文献信息

• A convenient synthesis of enantiomerically pure (R)-mexiletine using hydrolytic kinetic resolution method
  作者：Murugesan Sasikumar、Milind D. Nikalje、Murugan Muthukrishnan

  DOI：10.1016/j.tetasy.2009.11.014

  日期：2009.12

  Enantiopure (R)-mexiletine was prepared in a simple and practical way using hydrolytic kinetic resolution method of terminal epoxide by Jacobsen’s catalyst. High enantiomeric purity (98% ee) was achieved and the method is well amenable to industrial scale-up.

  对映体（R）-美西律汀是利用Jacobsen催化剂通过末端环氧化物的水解动力学拆分方法以简单实用的方式制备的。获得了高对映体纯度（98％ee），该方法非常适合工业规模放大。
• Piperidine derivatives
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0583971A1

  公开（公告）日：1994-02-23

  Compounds of formula (I): wherein:    R represents H or a mono- or poly- carboxylic acyl group;    R¹ represents H or a carboxylic ester moiety;    R² represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an aralkyl group, said groups being optionally substituted, or R² represents a carboxylic ester moiety;    n = 1 - 4;    Y is O or S;    and esters thereof,    are useful as heat and photo- stabilisers for polymeric materials.

  式(I)的化合物：其中：R代表H或单酰基或多酰基群；R¹代表H或羧酸酯基；R²代表烷基、烯基、炔基、芳基或芳基烷基，这些基团可选择性地被取代，或者R²代表羧酸酯基；n = 1 - 4；Y为O或S；及其酯，可用作聚合材料的热稳定剂和光稳定剂。
• Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers
  作者：Neeraj Bala、Swapandeep Singh Chimni、Harvinder Singh Saini、Bhupinder Singh Chadha

  DOI：10.1016/j.molcatb.2009.12.019

  日期：2010.5

  The phenyl glycidyl ether derivatives have been kinetically resolved with the growing cells of Bacillus alcalophilus MTCC10234 yielding (S)-epoxides with up to >99% ee and (R)-diols with up to 89% ee. The enantiomeric ratio (E) of up to 67 has been obtained for biohydrolysis process. The effect of different substituents of phenyl glycidyl ether on the biocatalytic efficiency of B. alcalophilus MTCC10234

  苯缩水甘油醚衍生物已经与嗜碱芽孢杆菌MTCC10234的生长细胞动力学分离，产生了（S）-环氧化合物，其ee含量高达> 99％，（R）-二醇的ee含量高达89％。对于生物水解过程，已获得高达67的对映体比率（E）。苯基缩水甘油基醚的不同取代基对嗜酸芽孢杆菌MTCC10234的生物催化效率的影响表明，甲基和氯取代的芳基缩水甘油基醚衍生物较为可取，而硝基衍生物的转化速度较慢。将含有在两个邻位均具有甲基的大体积芳基的2，6-二甲基苯基缩水甘油醚用N-甲基-N-二甲基苯甲酸酯进行拆分。E  = 39。
• EPOXY COMPOUND, EPOXY RESIN, CURABLE COMPOSITION, CURED PRODUCT THEREOF, SEMICONDUCTOR SEALING MATERIAL, AND PRINTED CIRCUIT BOARD
  申请人：DIC CORPORATION

  公开号：US20160130243A1

  公开（公告）日：2016-05-12

  There is provided an epoxy compound whose melt viscosity is low and which exhibits heat resistance and flame retardancy of a cured product; an epoxy resin which includes the same; curable composition and cured product; and semiconductor sealing material. The epoxy compound has a molecular structure represented by the following Formula (I): in the formula, G represents a glycidyl group, and X represents a structural site represented by the following Structural Formula (x1) or (x2); in Formula (x1) or (x2), k represents an integer of 1 to 3, m represents 1 or 2, Ar represents a structural site represented by the following Structural Formula (Ar1) or (Ar2), and when k or m represents 2 or greater, a plurality of Ar's may be the same as or different from each other: in Formula (3) or (4), G represents a glycidyl group, and p and r each independently represent 1 or 2.

  提供了一种环氧化合物，其熔融粘度低且固化产物具有耐热性和阻燃性；包括该环氧树脂的环氧树脂；可固化组合物和固化产物；以及半导体封装材料。该环氧化合物具有以下式（I）所表示的分子结构： 式中，G表示环氧基团，X表示由以下结构式（x1）或（x2）所表示的结构位; 在式（x1）或（x2）中，k表示1至3的整数，m表示1或2，Ar表示由以下结构式（Ar1）或（Ar2）所表示的结构位，当k或m表示2或更大时，多个Ar可以相同或不同： 在式（3）或（4）中，G表示环氧基团，p和r各自独立地表示1或2。
• Synthesis, α-adrenoceptors affinity and α1-adrenoceptor antagonistic properties of some 1,4-substituted piperazine derivatives
  作者：Marona、Kubacka、Filipek、Siwek、Dybala、Szneler、Pociecha、Gunia、Waszkielewicz, Anna M.

  DOI：10.1691/ph.2011.1543

  日期：——

  A series of different 1,4-substituted piperazine derivatives (1–11) was synthesized. It comprised 1-(substituted-phenoxyalkyl)-4-(2-methoxyphenyl)piperazine derivatives (1–5); 1,4-bis(substituted-phenoxyethyl)piperazine derivatives (6–8) and 1-(substituted-phenoxy)-3-(substituted-phenoxyalkylpiperazin-1-yl)propan-2-ol derivatives (9–11). All compounds were evaluated for affinity toward α1- and α2-receptors by radioligand binding assays on rat cerebral cortex using [3H]prazosin and [3H]clonidine as specific radioligand, respectively. Furthermore α1-antagonistic properties were checked for most promising compounds (1–5 and 10) by means of inhibition of phenylephrine induced contraction in isolated rat aorta. Antagonistic potency stayed in agreement with radioligand binding results. The most active compounds (1–5) displaced [3H]prazosin from cortical binding sites in low nanomolar range (Ki = 2.1–13.1 nM). Compound 10 showed slightly lower affinity for α1-adrenoceptor (Ki = 781 nM). Compounds 2–5 displayed the strongest antagonistic activity with pA2 values ranging from 8.441 to 8.807. Compound 1 gave a pA2 value of 7.868, while compound 10 showed the weakest antagonistic potency, giving a pA2 value of 6.374. 1-[3-(2-Chloro-6-methylphenoxy)propyl]-4-(2-methoxyphenyl)piperazine hydrochloride (5) showed the best α1- affinity properties with a Ki(α1) value of 2.1 nM and it was 61.05 fold more selective toward α1 than α2-receptors. The best properties showed 1-[3-(2,6-dimethylphenoxy)propyl]-4-(2-methoxyphenyl)piperazine hydrochloride (4) with a Ki(α1) value of 2.4 nM, a 142.13 fold better selectivity to α1- over α2-adrenoceptors and the best antagonistic potency (pA2 = 8.807). It is worth to emphasized that all most promising compounds possessed an 1-(o-methoxyphenyl)piperazine moiety which probably plays an important role in the affinity to α-adrenoceptors.

  合成了一系列不同的 1,4 取代哌嗪衍生物 (1-11)。其中包括 1-（取代的苯氧基烷基）-4-（2-甲氧基苯基）哌嗪衍生物（1-5）、1,4-双（取代的苯氧基乙基）哌嗪衍生物（6-8）和 1-（取代的苯氧基）-3-（取代的苯氧基烷基哌嗪-1-基）丙-2-醇衍生物（9-11）。通过在大鼠大脑皮层分别使用[3H]哌唑嗪和[3H]氯尼丁作为特异性放射性配体进行放射性配体结合试验，评估了所有化合物对α1-和α2-受体的亲和力。此外，通过抑制离体大鼠主动脉中由苯肾上腺素引起的收缩，检测了最有希望的化合物（1-5 和 10）的α1-拮抗特性。拮抗效力与放射性配体结合结果保持一致。活性最强的化合物（1-5）在低纳摩尔范围内（Ki = 2.1-13.1 nM）将[3H]哌唑嗪从皮质结合位点移出。化合物 10 对 α1 肾上腺素受体的亲和力稍低（Ki = 781 nM）。化合物 2-5 显示出最强的拮抗活性，pA2 值在 8.441 到 8.807 之间。化合物 1 的 pA2 值为 7.868，而化合物 10 的拮抗效力最弱，pA2 值为 6.374。1-[3-(2- 氯-6-甲基苯氧基)丙基]-4-(2-甲氧基苯基)哌嗪盐酸盐（5）显示出最佳的 α1 亲和性，Ki(α1) 值为 2.1 nM，它对α1 受体的选择性比对α2 受体的选择性高 61.05 倍。性能最好的是 1-[3-(2,6-二甲基苯氧基)丙基]-4-(2-甲氧基苯基)哌嗪盐酸盐（4），其 Ki(α1) 值为 2.4 nM，对α1-的选择性比对α2-肾上腺素受体的选择性高 142.13 倍，拮抗效力最好（pA2 = 8.807）。值得强调的是，所有最有前途的化合物都具有 1-（邻甲氧基苯基）哌嗪分子，这可能对α-肾上腺素受体的亲和力起着重要作用。