1-(5-Methyl-thiophen-2-ylmethyl)-1H-benzotriazole | 173258-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(5-Methyl-thiophen-2-ylmethyl)-1H-benzotriazole
• 英文别名: 1-[(5-methylthiophen-2-yl)methyl]benzotriazole
• CAS: 173258-81-6
• 化学式: C₁₂H₁₁N₃S
• 分子量: 229.305
• InChiKey: JZJNCPYXGLYBOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-Methyl-thiophen-2-ylmethyl)-1H-benzotriazole 在 正丁基锂 、 zinc dibromide 作用下， 以 氯仿 为溶剂， 反应 27.17h， 生成 2-methyl-5-(1,2,3,4-tetrahydronaphthalen-1-yl)thiophene
  参考文献：
  名称：

  Functionalized (Benzotriazol-1-yl)methanes as 1,1-Dipole Synthon Equivalents in Diverse Annulations to Aromatic and Heteroaromatic Rings

  摘要：

  The title compounds la-e readily undergo deprotonation and subsequent reactions with the appropriate electrophiles to form intermediates of types 4 and 7 which, upon treatment with Lewis acids, cyclize to afford fused aromatics 5 and 8. Tetrahydronaphthalene 11a, 1,2,3,4-tetrahydrochromanes (11b-d, 13), indanes (16, 18), 9,10-dihydrophenanthrenes (21a-c, 25), and tetrahydro[1,2-alpha]indoles (28, 30) with phenyl, substituted phenyl, and thienyl substituents were prepared in this manner.

  DOI：

  10.1021/jo972156w
• 作为产物：
  描述：

  2-甲基噻吩 、 1H-苯并三唑-1-甲醇 在 溶剂黄146 作用下， 反应 48.0h， 以50%的产率得到1-(5-Methyl-thiophen-2-ylmethyl)-1H-benzotriazole
  参考文献：
  名称：

  携带芳基和杂芳基基团的碳的一般和有效插入：α-芳基和α-杂芳基取代的酮的合成。

  摘要：

  由多种1-（芳基甲基）-和1-（杂芳基甲基）苯并三唑1与正丁基锂的锂化反应所形成的阴离子要加入脂族和芳族醛以及环状和非环状酮中。中间体在溴化锌存在下的随后原位热重排可在简单的一锅操作中以中等至优异的产率提供一碳链扩展或环扩展的α-芳基-和α-杂芳基取代的酮2在大多数情况下具有区域选择性。在1-（4-甲氧基苄基）苯并三唑（1e）与XC（6）H（4）COPh的插入反应中研究了取代基对相对迁移速率的影响。较小的负Hammett rho（+）值（-0.92）表明，重排通过早期的，类似试剂的电子不足的过渡态进行。

  DOI：

  10.1021/jo960841h

文献信息

• Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols
  作者：Alan R. Katritzky、Dorin Toader、Xiaojing Wang

  DOI：10.1021/jo980840k

  日期：1998.12.1

  Reactions of alpha-aryl-, alpha-heteroaryl-, and alpha-heteroatom-substituted masked alkenyllithiums with aldehydes and ketones provide a general method for the synthesis of allylic alcohols substituted with an aryl or heteroaryl in the beta position and aryl, heteroaryl or alkyl substituents in the a position via a [1,4]-C-->O silicon rearrangement. In the case of reactions with enolizable aldehydes and ketones, anhydrous CeCl3 was used as an additive. High diastereoselectivities are observed for allyl alcohols produced from a-substituted aldehydes.
• Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[<i>b</i>]thiophenes, and Polysubstituted Benzo[<i>b</i>]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes
  作者：Alan R. Katritzky、Larisa Serdyuk、Linghong Xie、Ion Ghiviriga

  DOI：10.1021/jo970672g

  日期：1997.9.1

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.
• General and Efficient Carbon Insertion Route to One-Carbon-Homologated .alpha.-Aryl, .alpha.-Alkenyl, .alpha.-Alkoxy, and .alpha.-Phenylthio Alkyl Ketones
  作者：Alan R. Katritzky、Linghong Xie、Dorin Toader、Larisa Serdyuk

  DOI：10.1021/ja00153a032

  日期：1995.12
• Katritzky, Alan R.; Wang, Junquan; Henderson, Scott A., Heterocycles, 1998, vol. 48, # 8, p. 1567 - 1574
  作者：Katritzky, Alan R.、Wang, Junquan、Henderson, Scott A.

  DOI：——

  日期：——
• Masked 2-Arylacroleins:  Versatile Three-Carbon Units for Organic Synthesis
  作者：Alan R. Katritzky、Dorin Toader、Christophe Chassaing、Diana C. Aslan

  DOI：10.1021/jo982493k

  日期：1999.8.1