1-(氯甲氧基)乙基苯 | 88023-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(氯甲氧基)乙基苯
• 英文名称: [1-(chloromethoxy)ethyl]benzene
• 英文别名: 1-(chloromethoxy)ethylbenzene
• CAS: 88023-77-2
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: CJIUXPHNZMDQEE-UHFFFAOYSA-N

物化性质

• 沸点：
  84-86 °C(Press: 0.01 Torr)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(氯甲氧基)乙基苯 在 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到2-苯基-1-丙醇
  参考文献：
  名称：

  氯甲基醚的[1,2] -Wittig重排

  摘要：

  不同的氯甲基醚1与过量的锂粉和催化量的4,4'-二叔丁基联苯（2.5 mol％）在THF中在0°C下反应，生成相应的α-硫代甲基醚中间体氯-锂交换，自发进行干净的[1,2]-维蒂希重排，提供预期的高苄醇2。这是从容易获得的氯甲基醚开始的这种重排的第一个版本。

  DOI：

  10.1016/j.tet.2006.08.028
• 作为产物：
  描述：

  α-Phenylethyl-methylthiomethylether 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到1-(氯甲氧基)乙基苯
  参考文献：
  名称：

  A New Synthesis of Chloromethyl Benzyl Ethers

  摘要：

  DOI：

  10.1055/s-1983-30506

文献信息

• 1,6-Bis[(benzyloxy)methyl]uracil derivatives—Novel antivirals with activity against HIV-1 and influenza H1N1 virus
  作者：Alexander N. Geisman、Vladimir T. Valuev-Elliston、Alexander A. Ozerov、Anastasia L. Khandazhinskaya、Alexander O. Chizhov、Sergey N. Kochetkov、Christophe Pannecouque、Lieve Naesens、Katherine L. Seley-Radtke、Mikhail S. Novikov

  DOI：10.1016/j.bmc.2016.04.010

  日期：2016.6

  A series of 1,6-bis[(benzyloxy)methyl]uracil derivatives combining structural features of both diphenyl ether and pyridone types of NNRTIs were synthesized. Target compounds were found to inhibit HIV-1 reverse transcriptase at micro- and submicromolar levels of concentrations and exhibited anti-HIV-1 activity in MT-4 cell culture, demonstrating resistance profile similar to first generation NNRTIs

  合成了一系列的1,6-双[（苄氧基）甲基]尿嘧啶衍生物，结合了二苯醚和吡啶酮类型的NNRTIs的结构特征。发现目标化合物可在微摩尔和亚微摩尔浓度下抑制HIV-1逆转录酶，并在MT-4细胞培养物中表现出抗HIV-1活性，显示出与第一代NNRTIs相似的耐药性。合成的化合物还显示出在MDCK细胞培养物中针对流感病毒（H1N1）的强大活性，而没有可检测的细胞毒性。该测定法的先导化合物的活性似乎超过了金刚乙胺，金刚烷胺，利巴韦林和奥司他韦羧酸盐。1，6-双[（苄氧基）甲基]尿嘧啶对流感病毒的作用机理目前正在研究中。
• METHOD FOR PRODUCING BIPHENYL DERIVATIVE
  申请人：Toray Fine Chemicals Co., Ltd.

  公开号：EP2075241A1

  公开（公告）日：2009-07-01

  Provided is a method for producing a biphenyl derivative, with an industrially high yield and excellent productivity, by use of a raw material which is low in cost and toxicity. More specifically, the method for producing the biphenyl derivative represented by general formula (1) is characterized in that a chlorine atom in a benzene derivative represented by general formula (2) reacts with magnesium metal to convert the benzene derivative into a Grignard reagent, and then the Grignard reagent is subjected to a coupling reaction in the presence of a catalyst and a dichloropropane: and (wherein A represents at least one selected from alkyl groups, alkoxy groups, alkoxymethyl groups, a vinyl group, phenyl groups and chlorine, and n represents an integer of 1 to 4).

  本发明提供了一种利用低成本、低毒性的原材料生产联苯衍生物的方法，该方法具有工业高产率和出色的生产率。更具体地说，通式（1）代表的联苯衍生物的生产方法的特点是：通式（2）代表的苯衍生物中的氯原子与金属镁反应，将苯衍生物转化成格氏试剂，然后格氏试剂在催化剂和二氯丙烷存在下进行偶联反应： 和（其中 A 代表至少一个选自烷基、烷氧基、烷氧基甲基、乙烯基、苯基和氯的基团，n 代表 1 至 4 的整数）。
• Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals
  作者：Cam-Van T. Vo、T. Andrew Mitchell、Jeffrey W. Bode

  DOI：10.1021/ja205174c

  日期：2011.9.7

  Mixed acetals and organotrifluoroborates undergo BF3 center dot OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF3 center dot OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 degrees C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.
• Pyrimidinones as reversible metaphase arresting agents
  作者：T Benneche、P Strande、R Oftebro、K Undheim

  DOI：10.1016/0223-5234(93)90014-6

  日期：1993.1

  5-Halo-N(1)-substituted 2(1H)-pyrimidinones have the ability to cause reversible arrest of mitosis during metaphase, Highly active compounds have a heteroatom (O, S or N) in the beta-position of the N(1)-carbon chain which is further substituted by an aryl group. In vitro data have been provided. It is suggested that reversible metaphase inhibitors can be used as synchronizing agents of cell-cycles by applying them in a sequential manner when a phase-specific cytotoxic drug is used in the treatment of diseases caused by uncontrolled rapidly proliferating cells. The active compounds are prepared from 2-pyrimidinones by alkylation reactions. The key reactants are alpha-chloroalkyl ethers, sulfides and amides; methods for their syntheses have been described.
• METHOD FOR PRODUCING A BIPHENYL DERIVATIVE
  申请人：Toray Fine Chemicals Co., Ltd.

  公开号：EP2075241B1

  公开（公告）日：2013-09-25