5-氯-1,2-苯并二硫醇-3-酮 | 138553-26-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 5-氯-1,2-苯并二硫醇-3-酮
• 英文名称: 5-chloro-3H-benzo[c][1,2]dithiol-3-one
• 英文别名: 5-Chloro-3H-1,2-benzodithiol-3-one；5-chloro-1,2-benzodithiol-3-one
• CAS: 138553-26-1
• 化学式: C₇H₃ClOS₂
• 分子量: 202.685
• InChiKey: CPGSEUYINMZOAT-UHFFFAOYSA-N

物化性质

• 沸点：
  389.1±44.0 °C(Predicted)
• 密度：
  1.609±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：
  0.0
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯-1,2-苯并二硫醇-3-酮 在 二甲基二环氧乙烷 作用下， 反应 2.0h， 生成 5-chloro-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one
  参考文献：
  名称：

  Substituent Effects on the Reactivity of Benzo-1,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs

  摘要：

  [GRAPHICS]The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3-one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.

  DOI：

  10.1021/jo0508191
• 作为产物：
  描述：

  5-氯-2-巯基苯甲酸 在 硫酸 、 硫代乙酸 作用下， 反应 0.25h， 生成 5-氯-1,2-苯并二硫醇-3-酮
  参考文献：
  名称：

  Substituent Effects on the Reactivity of Benzo-1,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs

  摘要：

  [GRAPHICS]The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3-one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.

  DOI：

  10.1021/jo0508191
• 作为试剂：
  描述：

  丙烷-1-硫醇 在 5-氯-1,2-苯并二硫醇-3-酮 作用下， 以 氘代乙腈 、 重水 为溶剂， 反应 0.25h， 生成 二丙基三硫醚 、 二丙基四硫化物 、 二丙基二硫
  参考文献：
  名称：

  Substituent Effects on the Reactivity of Benzo-1,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs

  摘要：

  [GRAPHICS]The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3-one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.

  DOI：

  10.1021/jo0508191

文献信息

• Switchable Copper-Catalyzed Approach to Benzodithiole, Benzothiaselenole, and Dibenzodithiocine Skeletons
  作者：Meng-Qiao Huang、Tuan-Jie Li、Jian-Quan Liu、Andrey Shatskiy、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.orglett.0c00907

  日期：2020.5.1

  A copper-catalyzed reaction between 2-bromo-benzothioamides and S8 or Se involving sulfur rearrangement is reported, enabling access to benzodithioles 2 and benzothiaselenoles 6 in the presence of Cs2CO3. In the absence of S8 or Se, the reaction affords dibenzodithiocines 7 via two consecutive C(sp2)-S Ullmann couplings.

  据报道2-溴-苯并硫代酰胺与S8或Se之间的铜催化反应涉及硫的重排，在存在Cs2CO3的情况下，可与苯并二硫代2和苯并噻吩并茂的6接触。在不存在S 8或Se的情况下，该反应通过两个连续的C（sp 2）-S Ullmann偶合提供二苯并二硫代7。
• 一种苯并二硫杂环戊烯类骨架化合物的制备 方法
  申请人：江苏师范大学

  公开号：CN110950836B

  公开（公告）日：2022-04-05

  本发明公开了一种苯并二硫杂环戊烯类骨架化合物的制备方法，将2‑溴硫代苯甲酰胺衍生物和S8加入有机溶剂中，再加入配体和碱，惰性气氛中在铜催化剂作用下反应，然后将反应体系经抽滤和酸性水解处理，即得。本发明具有操作简单，原料和试剂易得，条件温和，反应体系绿色环保，产物易分离纯化的优点，适用于合成多种苯并二硫杂环戊烯类骨架化合物，特别适用于大规模的工业生产，可以高效、高收率地制得高纯度的苯并二硫杂环戊烯类骨架化合物，产物收率最高可达91％。
• Assembly of Benzo[<i>c</i>][1,2]dithiol-3-ones via Acid-Promoted Denitrogenative Transannulation of Benzotriazinones
  作者：Yao Zhou、Bohao Zhang、Junjie Dong、Jingnan Li、Shanhong Yang、Likun Ye

  DOI：10.1021/acs.orglett.2c03638

  日期：2022.12.16

  An expedient synthesis of benzo[c][1,2]dithiol-3-ones via metal-free denitrogenative transannulation of benzotriazinones is developed, which represents the first example of acid-mediated heteroannulation of benzotriazinones. This newly discovered reactivity of benzotriazinones enables the streamline synthesis of diverse benzo[c][1,2]dithiol-3-ones in decent yields by using sodium sulfide as the sulfur

  通过苯并三嗪酮的无金属脱氮环环化，开发了苯并[ c ][1,2]二硫醇-3-酮的便捷合成方法，这是酸介导苯并三嗪酮杂环化的第一个例子。这种新发现的苯并三嗪酮的反应活性使得通过使用硫化钠作为硫源在简单的反应条件下能够以良好的产率简化合成各种苯并[ c ][1,2]二硫醇-3-酮。
• Synthesis of Benzo[e][1,3]thiazin‐4‐ones via PPh₃‐Promoted Cyclization of Benzo[c][1,2]dithiol‐3‐ones and Amidines
  作者：Xiaobing Liu、Wenxin Lv、Junjie Dong、Zekai Liu、Feng Hu、Chuncheng Zhou、Yao Zhou

  DOI：10.1002/adsc.202301504

  日期：——

  A metal‐free cyclization of benzo[c][1,2]dithiol‐3‐ones and amidines is demonstrated herein. Triphenylphosphine was harnessed as the activating reagent to facilitate the ring‐opening of benzo[c][1,2]dithiol‐3‐ones via S‐S bond cleavage. This PPh3‐Promoted cyclization reaction of benzo[c][1,2]dithiol‐3‐ones enabled to forge a diverse array of 1,3‐benzothiazones in good yields with wide substrate scope

  本文证明了苯并[c][1,2]二硫醇-3-酮和脒的无金属环化。利用三苯基膦作为活化剂，通过 S-S 键断裂促进苯并[c][1,2]二硫醇-3-酮的开环。这种 PPh3 促进的苯并[c][1,2]二硫醇-3-酮环化反应能够在温和条件下以良好的收率和广泛的底物范围形成多种 1,3-苯并噻腙。