2-methylcyclopent-1-en-1-yl trifluoromethanesulfonate | 57155-02-9

• 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: 2-methylcyclopent-1-en-1-yl trifluoromethanesulfonate
• 英文别名: 2-Methyl-1-cyclopenten-1-yl triflate；Trifluoromethanesulfonic acid 2-methyl-1-cyclopentene-1-yl ester；(2-methylcyclopenten-1-yl) trifluoromethanesulfonate
• CAS: 57155-02-9
• 化学式: C₇H₉F₃O₃S
• 分子量: 230.208
• InChiKey: XQFRIKPFJMPNQV-UHFFFAOYSA-N

物化性质

• 沸点：
  237.7±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methylcyclopent-1-en-1-yl trifluoromethanesulfonate 以 乙醇 、 水 为溶剂， 反应 168.0h， 生成 2-甲基环戊酮
  参考文献：
  名称：

  Hanack, Michael; Maerkl, Rainer; Martinez, Antonio Garcia, Chemische Berichte, 1982, vol. 115, # 2, p. 772 - 782

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 2-甲基环戊酮 在 lithium diisopropyl amide 作用下， 生成 2-methylcyclopent-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Stereoselective Construction of the Dicyclopenta[a,d]cyclooctene Core of the Ceroplastin Sesterterpenes by Way of the Anionic Oxy-Cope Rearrangement

  摘要：

  Bicyclo[3.2.1]octanediones such as 9, which are readily available by double carbonylation of (1,3-cyclohexadiene)iron tricarbonyl complexes according to Eilbracht, are amenable to regiospecific methylenation under Wittig conditions. Reduction of 10 with copper hydride leads to 11, which can be resolved by application of Johnson's sulfoximine technology and oxidized to give the enantiopure antipodes of 10. Variously substituted cyclopentenyl anions undergo 1,2-addition to 10, providing carbinols which are capable of anionic oxy-Cope rearrangement via chair transition states. These structural reorganizations are fully stereocontrolled and lead directly to functionalized dicyclopenta[a,d]cyclooctenes. When 11 is treated analogously, only [1,3] sigmatropy is observed and inversion of stereochemistry at the migrating carbon prevails. Both processes exhibit impressive scaffolding powers and are characterized by brevity.

  DOI：

  10.1021/jo952165+

文献信息

• Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates
  作者：Tucker R. Huffman、Yebin Wu、Alexis Emmerich、Ryan A. Shenvi

  DOI：10.1002/anie.201813233

  日期：2019.2.18

  Pd0 -catalyzed Mizoroki-Heck reactions traditionally exhibit poor reactivity with polysubstituted, unbiased alkenes. Intermolecular reactions with simple, all-carbon tetrasubstituted alkenes are unprecedented. Herein we report that pendant carboxylic acids, combined with bulky monophospine ligands on palladium, can direct the arylation of tri- and tetrasubstituted olefins. Quaternary carbons are established

  传统上，Pd0催化的Mizoroki-Heck反应与多取代，无偏烯烃的反应性较差。与简单的全碳四取代烯烃的分子间反应是前所未有的。在本文中，我们报道侧链羧酸与钯上的庞大单膦配体结合，可以指导三和四取代烯烃的芳基化。在高Fsp3连接环连接处建立季碳，并且偶联后可以除去羧酸酯导向基团。羧酸根的方向性可防止新的，取代度较低的烯烃过度芳基化，而后者在随后的反应中可能会多样化。
• [EN] TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE TRIPEPTIDE ÉPOXY CÉTONE PROTÉASE
  申请人：ONYX THERAPEUTICS INC

  公开号：WO2014152134A1

  公开（公告）日：2014-09-25

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂，它们的制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了式（X）的化合物：以及包括它们的药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗炎症和神经退行性疾病等疾病。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSES HETEROCYCLIQUES ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：MERCK & CO INC

  公开号：WO2001016121A1

  公开（公告）日：2001-03-08

  In accordance with the present invention, there are provided novel class of heterocyclic compounds and methods of use thereof. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. At a ring position adjacent to a ring nitrogen atom, the heterocyclic ring has at least one substituent which includes a moiety, linked to the heterocyclic ring via an alkylene moiety, an alkynylene moiety or an azo group. Invention compounds are capable of a wide variety of uses including modulating physiological processes by functioning as agonists and antagonists of receptors in the nervous system, as insecticides, and as fungicides. The invention further provides methods of modulating the activity of excitatory amino acid receptors using a specifically defined class of heterocyclic compounds including the novel compounds referred to above. In one embodiment, there are provided methods of modulating metabotropic glutamate receptors. The present invention also discloses methods of treating disease using heterocyclic compounds. The invention further discloses methods of preventing disease conditions related to diseases of the pulmonary system, diseases of the nervous system, diseases of the cardiovascular system, diseases of the gastrointestinal system, diseases of the endocrine system, diseases of the exocrine system, diseases of the skin, cancer and diseases of the ophthalmic system. The invention also discloses pharmaceutically acceptable salt forms of the above-described heterocyclic compounds.

  根据本发明，提供了一类新型的杂环化合物及其使用方法。该发明的化合物包含一个取代的、不饱和的五、六或七元杂环环，其中至少包含一个氮原子和至少一个碳原子。在靠近环氮原子的环位置上，杂环环有至少一个取代基，包括一个官能团，通过烷基官能团、炔基官能团或偶氮基团连接到杂环环上。发明的化合物能够广泛应用，包括通过作为神经系统受体的激动剂和拮抗剂来调节生理过程，作为杀虫剂和杀菌剂。本发明还提供了使用特定定义的杂环化合物类来调节兴奋性氨基酸受体活性的方法，包括上述新型化合物。在一种实施例中，提供了调节代谢性谷氨酸受体的方法。本发明还揭示了使用杂环化合物治疗疾病的方法。本发明还揭示了预防与肺系统疾病、神经系统疾病、心血管系统疾病、胃肠系统疾病、内分泌系统疾病、外分泌系统疾病、皮肤疾病、癌症和眼科系统疾病相关的疾病状态的方法。本发明还揭示了上述杂环化合物的药物可接受的盐形式。
• TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS
  申请人：Onyx Therapeutics, Inc.

  公开号：US20140336106A1

  公开（公告）日：2014-11-13

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.

  本文提供了三肽环氧酮蛋白酶抑制剂及其制备方法、相关药物组合物和使用方法。例如，本文提供了式（X）的化合物及其药物可接受的盐和组合物。本文提供的化合物和组合物可以用于治疗包括炎症和神经退行性疾病在内的疾病。
• Synthesis towards Phainanoid F: Photo‐induced 6π‐Electrocyclization for Constructing Contiguous All‐Carbon Quaternary Centers
  作者：Hao‐Yuan Liu、Zhen‐Yu Zhang、Yi‐Ke Zhou、Jia‐Hua Chen、Zhen Yang、Yuan‐He Li

  DOI：10.1002/asia.202300622

  日期：2023.10.17

  In this paper, we report an efficient strategy for synthesizing the DEFGH rings of phainanoid F. The key to the construction of the 13,30‐cyclodammarane skeleton of the molecule was a photo‐induced 6π‐electrocyclization and a homoallylic elimination. Notably, this is a rare example of using electrocyclization reaction to simultaneously construct two vicinal quaternary carbons in total synthesis. The strategy outlined here forms the basis of our total synthesis of Phainanoid F, and it could also serve as a generally applicable approach for synthesizing other natural products containing similar 13,30‐cyclodammarane skeletons.

  本文报告了一种合成辉南酮类化合物 F 的 DEFGH 环的高效策略。构建该分子的 13,30-Cyclodammarane 骨架的关键是光诱导的 6π 电环化反应和同源烯丙基消除反应。值得注意的是，这是利用电环化反应在全合成过程中同时构建两个邻位季碳的罕见实例。本文概述的策略构成了我们全合成辉南酮 F 的基础，它也可以作为一种普遍适用的方法，用于合成其他含有类似 13,30 环香豆素骨架的天然产物。