Ethyl 2-methyl-4-(trifluoromethylsulfonyloxy)cyclohexa-1,3-diene-1-carboxylate | 95455-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Ethyl 2-methyl-4-(trifluoromethylsulfonyloxy)cyclohexa-1,3-diene-1-carboxylate
• CAS: 95455-71-3
• 化学式: C₁₁H₁₃F₃O₅S
• 分子量: 314.282
• InChiKey: CLXSHIHETQVHSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-methyl-4-(trifluoromethylsulfonyloxy)cyclohexa-1,3-diene-1-carboxylate 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+/-) 1,2-epoxy-2-ethyl-5,7-dihydroxy-1,2,3,4-tetrahydro-6,11-naphthacenedione
  参考文献：
  名称：

  11-脱氧蒽环素酮系列中四环烯烃的一般和区域专一性路线：在（±）-金霉素的全合成中的应用

  摘要：

  从哈格曼的起始酯新烯酮的制备缩醛图4a和图4b以及它们与胡桃醌衍生物的环加成，得到LL-deoxytetracyclic烯烃20和21被进一步描述的第一全合成（±）-auramycinone（8）已经从完成20在距juglone仅9步之遥。

  DOI：

  10.1016/s0040-4020(01)91536-4
• 作为产物：
  描述：

  三氟甲磺酸酐 、 Hagemann's ester 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以74%的产率得到Ethyl 2-methyl-4-(trifluoromethylsulfonyloxy)cyclohexa-1,3-diene-1-carboxylate
  参考文献：
  名称：

  The conversion of vinyl triflates into γ'-hydroxy-α,β-enones

  摘要：

  Vinyl triflates have been converted into gamma'-hydroxy-alpha,beta-enones through their palladium-catalysed coupling with 1-butyn-4-ols followed by the reaction of the obtained 1-hydroxy-3-yn-5-enes in an acidic CH2Cl2/3 N HCl two-phase system in the presence of the n-BuN4Cl/PdCl2 combination. Both the coupling step and the conversion of the carbon-carbon triple bond into the ketonic group have been performed at room temperature. The conversion of vinyl triflates into gamma'-hydroxy-alpha,beta-enones can be carried out through a one-flask process, without the isolation of 1-hydroxy-3-yn-5-enes.

  DOI：

  10.1016/s0040-4020(01)80412-9

文献信息

• <b>Preparation of Indoles from </b> <b><i>o</i></b> <b>-Alkynyltrifluoroacetanilides Through the Aminopalladation­-Reductive Elimination Process</b>
  作者：Sandro Cacchi、Giancarlo Fabrizi、Luca Parisi

  DOI：10.1055/s-2004-815993

  日期：——

  The functionalized pyrrole nucleus contained in the indole system has been assembled via the palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with organic halides/triflates or allyl carbonates. In the presence of carbon monoxide, a three-component reaction can take place and indole derivatives incorporating a molecule of carbon monoxide have been obtained.

  吲哚体系中所含的官能化吡咯核通过邻炔基三氟乙酰苯胺与有机卤化物/三氟甲磺酸酯或碳酸烯丙酯的钯催化反应组装而成。在一氧化碳存在的情况下，可以发生三组分反应，并获得掺入一氧化碳分子的吲哚衍生物。
• Indole[1,2-c]quinazolines by Palladium-Catalyzed Cyclization of Bis(o-trifluoroacetamidophenyl) acetylene with Aryl and Vinyl Halides or Triflates
  作者：Antonio Arcadi、Sandro Cacchi、Alberto Cassetta、Giancarlo Fabrizi、Luca M. Parisi

  DOI：10.1055/s-2001-17458

  日期：——

  6-Trifluoromethyl-12-aryl(vinyl)indolo[1,2-c]quinazolines are prepared in high yield through the palladium-catalyzed reaction of readily available bis(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and triflates, followed by cyclization of the resultant derivatives. The reaction, which tolerates a variety of important functional groups, probably involves the formation of a 3-aryl-

  6-三氟甲基-12-芳基（乙烯基）吲哚并[1,2-c]喹唑啉是通过容易获得的双（邻三氟乙酰氨基苯基）乙炔与芳基或乙烯基卤化物和三氟甲磺酸酯的钯催化反应以高收率制备的，然后是所得衍生物的环化。该反应可以耐受各种重要的官能团，可能涉及形成 3-芳基-2-（邻三氟乙酰氨基苯基）吲哚中间体，然后环化为吲哚喹唑啉产物。吲哚喹唑啉核的形成已通过 X 射线分析明确确定。
• Palladium-Catalyzed Hydrovinylation of Vinyl Triflates with Alkynes An Approach to the Synthesis of 3-Vinylfuran-2(5H)-ones
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Fabio Marinelli、Paola Pace

  DOI：10.1002/(sici)1099-0690(199912)1999:12<3305::aid-ejoc3305>3.0.co;2-o

  日期：1999.12

  The reaction of alkynes with vinyl triflates in the presence of catalytic amounts of Pd(OAc)2 and HCOOK, omitting phosphane ligands, affords hydrovinylation products usually in good to high yields. The reaction has been employed to develop a regioselective synthesis of 3-vinylfuran-2(5H)-ones from methyl 4-hydroxy-2-butynoates.

  在催化量的 Pd(OAc)2 和 HCOOK 存在下，炔烃与乙烯基三氟甲磺酸酯的反应，省略磷烷配体，通常以良好到高产率提供加氢乙烯基化产物。该反应已被用于从 4-羟基-2-丁酸甲酯开发 3-乙烯基呋喃-2(5H)-酮的区域选择性合成。
• Synthesis of oxygen heterocycles via Pd-catalyzed cross-coupling of unsaturated phenols and vinylic halides or triflates
  作者：R.C. Larock、H. Yang、P. Pace、K. Narayanan、C.E. Russell、S. Cacchi、G. Fabrizi

  DOI：10.1016/s0040-4020(98)00399-8

  日期：1998.6

  palladium-catalyzed cross-coupling of o-allylic and o-vinylic phenols with vinylic halides and triflates produces substituted dihydrobenzopyrans and dihydrobenzofurans respectively in good to high yields. The proposed mechanism involves vinylpalladium addition to the olefin, rearrangement to a π-allylpalladium intermediate and subsequent intramolecular nucleophilic displacement of palladium.

  钯催化的邻烯丙基和邻乙烯基酚与乙烯基卤化物和三氟甲磺酸酯的交叉偶联分别以良好或高收率产生了取代的二氢苯并吡喃和二氢苯并呋喃。所提出的机理包括乙烯基钯加到烯烃中，重排成π-烯丙基钯中间体和随后的分子内亲核置换钯。
• Palladium-catalyzed cross-coupling of unsaturated phenols with vinylic halides and triflates
  作者：Richard C. Larock、Hoseok Yang、Paola Pace、Sandro Cacchi、Giancarlo Fabrizi

  DOI：10.1016/s0040-4039(97)10502-0

  日期：1998.1

  The palladium-catalyzed cross-coupling of o-vinylic phenols with vinylic halides and triflates produces substituted dihydrobenzopyrans and dihydrobenzofurans respectively in good to high yields.

  钯催化的邻乙烯基酚与乙烯基卤化物和三氟甲磺酸酯的交叉偶联分别以高至高收率产生了取代的二氢苯并吡喃和二氢苯并呋喃。