萘并[2,1-b]噻吩-1(2H)-酮 | 82-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘并[2,1-b]噻吩-1(2H)-酮
• 中文别名: (1Z)-3-叔-丁氧基-2-氯丙-1-烯-1-基二甲基磷酸酯
• 英文名称: naphtho[2,1-b]thiophen-1(2H)-one
• 英文别名: benzo[e][1]benzothiol-1-one
• CAS: 82-60-0
• 化学式: C₁₂H₈OS
• mdl: MFCD00997086
• 分子量: 200.261
• InChiKey: KLRNDFGOYWAXOU-UHFFFAOYSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  385.7±22.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  萘并[2,1-b]噻吩-1(2H)-酮 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 1-(1-hydroxynaphtho[2,1-b]thiophen-2-yl)ethan-1-one
  参考文献：
  名称：

  Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones

  摘要：

  Chemoselective synthesis of thioaurones or 3-hydroxy benzo[b]thiophen-2-aryl ketones, 1-hydroxy naphtho[2,1-b]thiophen-2aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzo[b]thiophen-2-yl) alkylates and (naphtho[2, 1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzo[b]thiophen-2-yl) and (1-hydroxy naphtho[2, 1 -b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.050
• 作为产物：
  描述：

  N,N-二乙基-1-萘羧酰胺 在 四甲基乙二胺 、 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 萘并[2,1-b]噻吩-1(2H)-酮
  参考文献：
  名称：

  Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones

  摘要：

  Chemoselective synthesis of thioaurones or 3-hydroxy benzo[b]thiophen-2-aryl ketones, 1-hydroxy naphtho[2,1-b]thiophen-2aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzo[b]thiophen-2-yl) alkylates and (naphtho[2, 1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzo[b]thiophen-2-yl) and (1-hydroxy naphtho[2, 1 -b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.050

文献信息

• Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2H)-ones
  作者：Koichi Mitsudo、Seiji Suga、Nanae Habara、Yoshiaki Kobashi、Yuji Kurimoto、Hiroki Mandai

  DOI：10.1055/s-0040-1707280

  日期：2020.12

  A one-pot procedure for the synthesis of thienyl thioethers is described. Several thienyl thioethers were synthesized by a TfOH-promoted Friedel–Crafts-type cyclization, a subsequent nucleophilic attack by an arenethiol, and dehydration. This protocol was successfully applied to the synthesis of thienoacene derivatives by using a Pd-catalyzed dehydrogenative cyclization.

  描述了一种用于合成噻吩硫醚的一锅法。通过TfOH促进的Friedel-Crafts型环化反应、随后的芳基硫醇亲核攻击和脱水反应，合成了几种噻吩硫醚。该方案成功应用于通过Pd催化的脱氢环化合成噻吩芳香烃衍生物。

• NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines
  作者：Youquan Zhang、Aimin Yu、Jiru Jia、Shanshan Ma、Ke Li、Yin Wei、Xiangtai Meng

  DOI：10.1039/c7cc04466f

  日期：——

  The [4+3] annulation reaction of crotonic acid derivative sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported by DFT calculations.

  使用NaH作为碱，首次报道了己烯酸衍生硫代亚甲基与硫金酮的[4+3]环合反应。在良好至优异的产率下获得了多样的2,5-二氢苯并[4,5]噻吩[3,2-b]氧杂环戊二烯。拟议的机制经过DFT计算进行了研究并得到支持。
• Synthesis of Benzothiophene‐Fused Oxa[6.6.5]tricyclic Skeletons through a Cinchonidine‐ or NaOH‐Promoted Quadruple Domino Sequence
  作者：Ke Li、Liang Wang、Aimin Yu、Lingli Zhu、Lei Zhang、Yingchun Gu、Xiangtai Meng

  DOI：10.1002/chem.201900890

  日期：2019.7.22

  Two base‐promoted quadruple domino reactions between thioaurones and allylic phosphonium salts have been developed to synthesize benzothiophene‐fused oxa[6.6.5]tricyclic skeletons in moderate to good yields with excellent stereoselectivity and broad functional‐group tolerance. This is a simple and useful protocol for the rapid construction of the umbrella‐like oxa[6.6.5]tricyclic skeleton.

  已开发出硫代金龙和烯丙基磷鎓盐之间的两个碱促进的四聚体多米诺反应，以中等至良好的产率合成苯并噻吩稠合的氧杂[6.6.5]三环骨架，具有出色的立体选择性和宽泛的官能团耐受性。对于快速构建类似伞形的oxa [6.6.5]三环骨架，这是一个简单而有用的协议。
• Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer
  作者：Mikkel Krell-Jørgensen、Habiburrahman Zulfikri、Magnus Grage Bonnevie、Frederik Simonsen Bro、Asmus Ougaard Dohn、Luca Laraia

  DOI：10.1039/d2cc05548a

  日期：——

  We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties, as well as highly redshifted bipyrrole-containing HTIs inspired by conductive polymers.

  我们报告了含有吲哚的双稳态半硫代吲哚（HTI），具有单向定量光开关性能，以及受导电聚合物启发的高度红移的双吡咯含量HTI。
• Easily Accessible Substituted Heterocyclic Hemithioindigos as Bistable Molecular Photoswitches
  作者：Aurélie Gernet、Ahmed El Rhaz、Ludovic Jean

  DOI：10.1002/chem.202301160

  日期：2023.8.25

  Heterocyclic hemithioindigo chromophores are easily accessible from the condensation of aldehydes and thioindoxyl derivatives. Using electron-rich heterocycles leads to excellent photoswitching properties such as strong absorption in visible light, good absorption changes between two isomers, quantitative isomer interconversions in both directions and high thermal stability.

  杂环半硫靛蓝发色团很容易通过醛和硫吲哚酚衍生物的缩合获得。使用富电子杂环可实现优异的光开关性能，例如可见光强吸收、两种异构体之间良好的吸收变化、双向定量异构体互变以及高热稳定性。