O-ethyl (1-benzyltetrazol-5-yl)methylsulfanylmethanethioate | 201672-89-1

• 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: O-ethyl (1-benzyltetrazol-5-yl)methylsulfanylmethanethioate
• CAS: 201672-89-1
• 化学式: C₁₂H₁₄N₄OS₂
• 分子量: 294.401
• InChiKey: SRMZVNVUJVJSGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-ethyl (1-benzyltetrazol-5-yl)methylsulfanylmethanethioate 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 、 氯苯 为溶剂， 反应 1.0h， 生成 4-[2-(1-Benzyl-1H-tetrazol-5-yl)-ethyl]-5,6,7-trimethoxy-2-methyl-3,4-dihydro-2H-isoquinolin-1-one
  参考文献：
  名称：

  A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones

  摘要：

  :A variety of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones 6 can be prepared by a two step radical sequence: intermolecular xanthate transfer addition to an N-allylbenzamide followed by cyclisation onto the aromatic ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01561-5
• 作为产物：
  描述：

  1-苄基-5-(氯甲基)-1H-四唑 、 potassium ethyl xanthogenate 以 丙酮 为溶剂， 生成 O-ethyl (1-benzyltetrazol-5-yl)methylsulfanylmethanethioate
  参考文献：
  名称：

  四唑甲基和相关基团：方便地获得四唑和其他杂环衍生物

  摘要：

  通过使用黄原酸酯转移技术将5-四唑甲基自由基加到各种末端烯烃中，可以简单地引入四唑单元；相同的原理可以应用于其他杂环体系，例如咪唑和苯并噻唑。©1997 Elsevier ScienceLtd。保留所有权利。

  DOI：

  10.1016/s0040-4039(97)10457-9

文献信息

• Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations
  作者：Alexandru Gheorghe、Béatrice Quiclet-Sire、Xavier Vila、Samir Z. Zard

  DOI：10.1016/j.tet.2007.04.091

  日期：2007.7

  A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following

  已经探索了涉及自由基1，4-和1，2-芳基迁移的3-芳基哌啶和3-芳基吡咯烷的途径。对于哌啶，第一途径要求将黄原酸酯加到N-烯丙基芳基磺酰胺中，然后乙酰化并用月桂酰过氧化物处理，得到相应的1，4-芳基转移产物。酸性水解后，该化合物可转化为所需的哌啶衍生物。对于第二种哌啶方法，将α-酮黄药添加到14型烯烃中会导致1,2-芳基迁移，导致产生α，β-不饱和酯，该酯可通过氨或伯胺和氰基硼氢化钠的作用转化为哌啶。取代的3-芳基吡咯烷可以通过简单地以α-酰胺基取代的黄药开始而获得。
• Fluoroazaindolines by an Uncommon Radical ipso-Substitution of a C-F Bond
  作者：Yann Laot、Laurent Petit、Ngoc Diem My Tran、Samir Z. Zard

  DOI：10.1071/ch10422

  日期：——

  Trifluoroazaindoline derivatives are prepared using the first synthetically useful radical ipso-substitution of a fluorine atom. The initial procedure has been improved to allow the gram scale synthesis of these building blocks, which can be regioselectively substituted by nucleophiles under mild conditions to rapidly access a library of new molecules. Oxidation to the corresponding fluoroazaindole core has also been accomplished.

  三氟氮杂吲哚啉衍生物的制备首次使用了对合成有用的氟原子同位取代基。对最初的程序进行了改进，从而可以在克级规模上合成这些构筑基块，这些基块可以在温和的条件下被亲核物进行区域选择性取代，从而快速获得新分子库。氧化成相应的氟氮杂环吲哚核心的过程也已经完成。
• Synthesis of Fluoroazaindolines by an Uncommon Radical <i>ipso</i> Substitution of a Carbon−Fluorine Bond
  作者：Yann Laot、Laurent Petit、Samir Z. Zard

  DOI：10.1021/ol101240f

  日期：2010.8.6

  Rare examples of a synthetically useful radical ipso substitution of a carbon−fluorine bond are reported. Highly functionalized fluoroazaindoline structures have thus been prepared with use of cheap and readily available substrates and reagents.

  报道了碳-氟键在合成上有用的自由基ipso取代的例子。因此，已经使用廉价且容易获得的底物和试剂制备了高度官能化的氟氮杂二氢吲哚结构。
• Tin-Free Radical Cyclizations for the Synthesis of 7-Azaoxindoles, 7-Azaindolines, Tetrahydro[1,8]naphthyridines, and Tetrahydro-5<i>H</i>-pyrido[2,3-<i>b</i>]azepin-8-ones
  作者：Eric Bacqué、Myriem El Qacemi、Samir Z. Zard

  DOI：10.1021/ol0489649

  日期：2004.10.1

  Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro-[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.
• Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates
  作者：Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/jacs.5b03893

  日期：2015.6.3

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.