5-chloro-[1]benzothiophen-3(2H)-one | 51942-80-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-chloro-[1]benzothiophen-3(2H)-one
• 英文别名: 5-Chloro-1-benzothiophen-3-one
• CAS: 51942-80-4
• 化学式: C₈H₅ClOS
• 分子量: 184.646
• InChiKey: FAOXGZDAXLVEMH-UHFFFAOYSA-N

物化性质

• 沸点：
  325.4±42.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  5-chloro-[1]benzothiophen-3(2H)-one 在 哌啶 、 三(4-甲氧苯基)膦 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.25h， 生成 triethyl 2-chloro-10a,8-(epoxymethano)-7,10-methanobenzo[b]cyclohepta[d]thiophene-6,8,10(7H,9H)-tricarboxylate
  参考文献：
  名称：

  Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

  摘要：

  Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3(2H)-ones and Morita-Baylis-Hillamn (MBH) carbonate were developed. All domino reactions exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused alpha-pyran, 2,3-dihydrooxepine, and oxatricyclodecene derivatives. Furthermore, [4 + 2], [4 + 3], and related domino reactions from identical substrates can be controlled.

  DOI：

  10.1021/acs.orglett.7b02916
• 作为产物：
  描述：

  [(4-chlorophenyl)thio]acetyl chloride 在 三氯化铝 、 硝基甲烷 作用下， 以 二硫化碳 为溶剂， 反应 3.0h， 以42%的产率得到5-chloro-[1]benzothiophen-3(2H)-one
  参考文献：
  名称：

  Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; El-Zohry, Maher F., Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 31 - 44

  摘要：

  DOI：

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。
• Phosphine-Catalyzed Domino Reaction of Thioaurones and Allenoate: Synthesis of Benzothiophene-Fused Dioxabicyclo[3.3.1]nonane Derivatives
  作者：Shanshan Ma、Aimin Yu、Lei Zhang、Xiangtai Meng

  DOI：10.1021/acs.joc.8b00145

  日期：2018.5.18

  The reaction of thioaurone derivatives with allenoate catalyzed by tris(4-methoxyphenyl)phosphane (P(4-MeOC6H4)3) resulted in a domino annulation reaction to produce a benzothiophene-fused bridged bicyclic ring, with 40–91% yields. The advantages of the methodology include diastereoselective formation of a bridged bicyclic ring in a single step, very mild reaction conditions, and success resulting

  三（4-甲氧基苯基）膦（P（4-MeOC 6 H 4）3）催化的硫代金酮衍生物与脲基甲酸酯的反应导致多米诺环化反应，产生苯并噻吩稠合的桥连双环，产率为40-91％ 。该方法的优点包括在一个步骤中非对映选择性地形成桥接的双环，非常温和的反应条件以及由于广泛的官能团而获得的成功。DFT计算对提出的机制进行了测试和支持。
• A Preparation Of Methyl 2-amino-3-formylbenzoate and its use in Friedlander Synthesis
  作者：Xianyong Bu、Leslie W. Deady

  DOI：10.1080/00397919908085895

  日期：1999.12.1

  Abstract The title compound has been prepared in four steps from methyl isatin-7-carboxylate. Condensations with 1-indanone and analogs gave 11H-indeno[1,2-b]quinoline-6-carboxylic acids, and with cyclohexanones gave acridine-4-carboxylic acids.

  摘要 标题化合物由 7-羧酸甲酯经四步制备。与 1-茚满酮和类似物缩合得到 11H-茚并[1,2-b]喹啉-6-羧酸，与环己酮缩合得到吖啶-4-羧酸。
• 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。