methyl 1-oxo-2-((trifluoromethyl)thio)-2,3-dihydro-1H-indene-2-carboxylate | 1443036-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 1-oxo-2-((trifluoromethyl)thio)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: 1-Oxo-2-(trifluoromethylthio)-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester；methyl 3-oxo-2-(trifluoromethylsulfanyl)-1H-indene-2-carboxylate
• CAS: 1443036-48-3
• 化学式: C₁₂H₉F₃O₃S
• 分子量: 290.263
• InChiKey: KMULOKGYBZATIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.66h， 生成 methyl 1-oxo-2-((trifluoromethyl)thio)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Oxidative trifluoromethylselenolation of 1,3-dicarbonyls with [Me₄N][SeCF₃]

  摘要：

  1,3-二羰基化合物与[Me₄N][XCF₃]（X = Se 和 S）以及氧化剂进行的首次氧化三氟甲基硫、硒化反应被描述。

  DOI：

  10.1039/d0ob00108b

文献信息

• Structure–Reactivity Relationship of Trifluoromethanesulfenates: Discovery of an Electrophilic Trifluoromethylthiolating Reagent
  作者：Xinxin Shao、Chunfa Xu、Long Lu、Qilong Shen

  DOI：10.1021/jo502645m

  日期：2015.3.20

  A family of electrophilic trifluoromethanesulfenates was prepared. Structure–reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities. A simplified electrophilic trifluoromethylthiolating reagent 1c was then identified that can react with a wide range of nucleophiles such as Grignard

  制备了亲电三氟甲烷亚磺酸盐家族。结构反应关系研究表明，三氟甲基硫醇化试剂的芳基环上的取代基对其反应活性没有明显影响。然后鉴定出一种简化的亲电子三氟甲基硫醇化试剂1c，它可以在温和的反应条件下与格氏试剂，芳基硼酸，炔烃，吲哚，β-酮酸酯，羟吲哚和亚磺酸钠等多种亲核试剂反应。在这些条件下可以耐受多种官能团。
• Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β-Keto Esters
  作者：Yu-Dong Yang、Ayaka Azuma、Etsuko Tokunaga、Mikio Yamasaki、Motoo Shiro、Norio Shibata

  DOI：10.1021/ja402455f

  日期：2013.6.19

  A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride

  设计了一种新型的亲电型三氟甲硫基化试剂，一种三氟甲磺酰基高价碘鎓叶立德，并与各种亲核试剂反应良好，得到所需的 CF3S 取代产物。三氟甲磺酰基的原位还原得到三氟甲硫基，这是该过程中的关键步骤，是在氯化铜 (I) 存在下实现的。
• An Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation
  作者：Xinxin Shao、Xueqiang Wang、Tao Yang、Long Lu、Qilong Shen

  DOI：10.1002/anie.201209817

  日期：2013.3.18

  Sulfur and friends: A new electrophilic hypervalent iodine reagent 1 has been developed for direct trifluoromethylthiolation. A variety of nucleophiles, including β‐ketoesters, aldehydes, amides, aryl or vinyl boronic acids, and alkynes, reacted with 1 under mild conditions to give the corresponding trifluoromethylthiolated compounds in good to excellent yields.

  硫磺和朋友：已开发出一种新的亲电子高价碘试剂1用于直接三氟甲基硫醇化。各种亲核试剂（包括β-酮酸酯，醛，酰胺，芳基或乙烯基硼酸和炔烃）在温和的条件下与1反应，以良好的产率获得了相应的三氟甲基硫代化合物。
• Structural Reevaluation of the Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation Supported by the Crystalline Sponge Method for X-ray Analysis
  作者：Ekaterina V. Vinogradova、Peter Müller、Stephen L. Buchwald

  DOI：10.1002/anie.201310897

  日期：2014.3.17

  We further report a revised structure for the earlier described electrophilic trifluoromethylthiolation reagent (1), which was previously believed to contain the benziodoxole framework. Our findings, which are based on a combination of analytical techniques, including the recently introduced crystalline sponge method for X‐ray analysis, unambiguously demonstrate that 1 is a thioperoxy compound both

  高价碘 λ 3 -苯并氧杂环戊烷是常见的亲电转移试剂，与非环状类似物相比，它们具有更高的稳定性。在此我们提供的数据表明，氯代苯并氧杂环戊烷与两种不同的硫醇盐亲核试剂（硫氰酸盐和三氟甲基硫醇盐）反应，导致形成稳定的硫代过氧复合物，而不是预期的苯并氧杂环戊烷衍生物。我们进一步报告了先前描述的亲电三氟甲基硫醇化试剂 ( 1 )的修订结构，该试剂以前被认为包含苯并氧杂环戊烷骨架。我们的研究结果基于分析技术的组合，包括最近引入的用于 X 射线分析的结晶海绵方法，明确证明1 是溶液和固态的硫代过氧化合物。
• 2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions
  作者：Zhongyan Huang、Kenta Okuyama、Chen Wang、Etsuko Tokunaga、Xiaorui Li、Norio Shibata

  DOI：10.1002/open.201500225

  日期：2016.6

  2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one (diazo‐triflone) (2) is not only a building block but also a reagent. In this study, diazo‐triflone, which was originally used for the synthesis of β‐lactam triflones as a trifluoromethanesulfonyl (SO2CF3) building block under catalyst‐free thermal conditions, is redisclosed as an effective electrophilic trifluoromethylthiolation reagent under copper catalysis

  2-重氮-1-苯基-2-（（三氟甲基）磺酰基）乙-1-酮（重氮三酮）（2）不仅是构件，而且还是试剂。在这项研究中，重氮重氮酮原本是在无催化剂的热条件下以三氟甲磺酰基（SO 2 CF 3）结构单元的形式用于合成β-内酰胺三氟酮的，后来在铜催化下重新公开为有效的亲电子三氟甲基硫醇化试剂。将大量的烯胺，吲哚，β-酮酸酯，吡咯和苯胺很好地转化为相应的三氟甲硫基（SCF 3）在重铜催化下，通过亲电子型反应，重氮-三氢萘酮以高至高收率的化合物。重氮-三唑酮也可以以可接受的产率实现芳基碘的偶合型三氟甲基硫醇化反应。