(1-甲基-1H-2-咪唑基)(苯基)甲醇 | 30517-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (1-甲基-1H-2-咪唑基)(苯基)甲醇
• 中文别名: (1-甲基-1H-咪唑-2-基)(苯)甲醇
• 英文名称: (1-methyl-1H-imidazol-2-yl)-phenylmethanol
• 英文别名: (1-methyl-1H-imidazol-2-yl)(phenyl)methanol；(1-methylimidazol-2-yl)-phenylmethanol
• CAS: 30517-60-3
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD01055394
• 分子量: 188.229
• InChiKey: YJZWZSIAWLAIRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090
• WGK Germany：
  3
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310

反应信息

• 作为反应物：
  描述：

  (1-甲基-1H-2-咪唑基)(苯基)甲醇 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 phenyl(quinazolin-4-yl)methanone
  参考文献：
  名称：

  Synthesis and Reactivities of 1,3-Dimethyl-2-(a-hydroxybenzyl)imidazolium and 1,3-Dimethyl-2-(a-hydroxybenzyl)benzimidazolium Iodides

  摘要：

  1,3-Dimethyl-2-(alpha-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazolin (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine. (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(alpha-hydroxybenzyl)imidazo iodide (4a).

  DOI：

  10.3987/com-96-s40
• 作为产物：
  描述：

  [(1-methylimidazol-2-yl)-phenylmethyl] N,N-di(propan-2-yl)carbamate 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(1-甲基-1H-2-咪唑基)(苯基)甲醇
  参考文献：
  名称：

  一锅三组分反应合成2-取代的唑类

  摘要：

  我们发现了一种新的反应，其中在an鎓内鎓盐与反应性羰基化合物的反应中形成了2-取代的唑。这些产物在α位含有一个离去基团，在亲核试剂存在下进行溶剂分解时会生成带有多种α-取代基的唑。我们已经开发了这种化学方法的新方面，并将范围扩大到包括咪唑，噻唑，苯并咪唑和三唑，因此在两个反应步骤中获得了各种各样的取代方式。

  DOI：

  10.1016/s0040-4039(01)02110-4

文献信息

• Isoprene-catalyzed lithiation of imidazole: synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles
  作者：Rosario Torregrosa、Isidro M. Pastor、Miguel Yus

  DOI：10.1016/j.tet.2005.09.024

  日期：2005.11

  of isoprene (20 mol%) in THF at room temperature. By reacting this organolithium with carbonyl electrophiles 2-(hydroxyalkyl)imidazoles 3 were obtained, in good yields. As a result of the reaction of the mentioned lithium intermediate with imines 4, the corresponding 2-(aminoalkyl)imidazoles 5 were isolated in excellent yields.

  通过新方案制备2-锂硫代咪唑，该新方案由在室温下在THF中亚化学计量的异戊二烯（20摩尔％）存在下略有过量的锂金属组成。通过使该有机锂与羰基亲电试剂反应，以良好的产率获得了2-（羟烷基）咪唑3。作为上述锂中间体与亚胺4反应的结果，以优异的产率分离了相应的2-（氨基烷基）咪唑5。
• A New Method of Synthesizing Deoxybenzoins from 1,3-Dimethyl-2-(.ALPHA.-benzyloxybenzyl)imidazolium and 1,3-Dimethyl-2-(.ALPHA.-benzyloxybenzyl)benzimidazolium Iodides Based on Wittig-Type Rearrangement.
  作者：Akira MIYASHITA、Yoshiyuki MATSUOKA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.45.1235

  日期：——

  The treatment of 1, 3-dimethyl-2-(α-benzyloxybenxyl)benzimidazolium iodides 1 with a base gave deoxybenzoins 2 in moderate yields. Sodium hydride (NaH), potassium carbonate (K2CO3), and cesium carbonate (Cs2CO3) were effective bases in this reaction. Deoxybenzoins 2 were produced through rearrangement of the benzyl group followed by expulsion of the 1, 3-dimethylbenzimidazolium ylide (A). The rearrangement proceeds in a way similar to Witting rearrangement. Deoxybenzoins 2 were also formed in good yields from 1, 3-dimethyl-2-(α-benzyloxybenxyl)-imidazolium iodides 4 upon similar treatment. However, the quaternary salts having a thiazolium moiety 5a and a pyridinium moiety 6a failed to produce deoxybenzoin (2a).

  对1, 3-二甲基-2-(α-苄氧苄基)苯并咪唑铵碘化物1进行碱性处理后，得到中等产率的去氧苄酮2。氢化钠（NaH）、碳酸钾（K2CO3）和碳酸铯（Cs2CO3）在此反应中是有效的碱。去氧苄酮2是通过苄基的重排，随后排出1, 3-二甲基苯并咪唑铵烯体（A）而生成的。该重排过程类似于维廷重排。对1, 3-二甲基-2-(α-苄氧苄基)-咪唑铵碘化物4进行类似处理时，去氧苄酮2也以良好的产率形成。然而，具有噻唑铵基团5a和吡啶铵基团6a的季铵盐未能产生去氧苄酮（2a）。
• Abarca-Gonzalez, Belen; Jones, R. Alan; Medio-Simon, Mercedes, Synthetic Communications, 1990, vol. 20, # 3, p. 321 - 331
  作者：Abarca-Gonzalez, Belen、Jones, R. Alan、Medio-Simon, Mercedes、Quilez-Pardo, Juan、Sepulveda-Arques, Jose、Zaballos-Garcia, Elena

  DOI：——

  日期：——
• TERTOV B. A.; KOVALEV G. V.; FOMIN YU. K.; KOSHCHIENKO YU. V.; BURYKIN V.+, XIM.-FARMATSEVT. ZH. <KNFZ-AN>, 1976, 10, HO 2, 34-36
  作者：TERTOV B. A.、 KOVALEV G. V.、 FOMIN YU. K.、 KOSHCHIENKO YU. V.、 BURYKIN V.+

  DOI：——

  日期：——
• Synthesis and Reactivities of 1,3-Dimethyl-2-(a-hydroxybenzyl)imidazolium and 1,3-Dimethyl-2-(a-hydroxybenzyl)benzimidazolium Iodides
  作者：Akira Miyashita、Akihito Kurachi、Yoshiyuki Matsuoka、Noriko Tanabe、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-96-s40

  日期：——

  1,3-Dimethyl-2-(alpha-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazolin (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine. (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(alpha-hydroxybenzyl)imidazo iodide (4a).