ethyl (2E)-6-bromo-2-methyl-2-hexenoate | 202581-33-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E)-6-bromo-2-methyl-2-hexenoate
• 英文别名: (E)-ethyl 6-bromo-3-methylhex-2-enoate；ethyl (E)-6-bromo-2-methylhex-2-enoate；6-bromo-2-methyl-hex-2-ethyl enoate
• CAS: 202581-33-7
• 化学式: C₉H₁₅BrO₂
• 分子量: 235.121
• InChiKey: HFNWRUGKFBYUNS-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-6-bromo-2-methyl-2-hexenoate 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (+/-)-(2S)-2-[(2S)-1-benzyl-pyrrolidin-2-yl]-ethyl propionate
  参考文献：
  名称：

  α，β-不饱和酯的分子内胺基和亚胺基加成 非对映选择性串联环官能化和氢转移反应。

  摘要：

  [反应：见正文]以分子内氨基自由基环官能化和氢转移为特征的串联过程可提供具有反或非对映选择性的2,3-反式-二取代的吡咯烷。该策略扩展至亚氨基自由基使在串联过程的两个步骤中反式反吡咯啉均具有较高的1,2-诱导水平。

  DOI：

  10.1021/ol0160809
• 作为产物：
  描述：

  ethyl (E)-2-methyl-6-(6-tetrahydropyran-2-yl)oxy-2-hexenate 在 四溴化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl (2E)-6-bromo-2-methyl-2-hexenoate
  参考文献：
  名称：

  Synthetic studies toward potent cytotoxic agents amphidinolides: Synthesis of the C1C18 moiety of amphidinolides G, H and L

  摘要：

  Stereoselective synthesis of the (8S, 9S, 11R, 16S)-C-1-C-18 Segment 1 of amphidinolides G, H and L, bearing the unique trisubstituted "s-cis-1,3-diene" moiety (C-28(29)=C-13-C-14=C-15), has been achieved for the first time following a highly efficient convergent strategy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02009-7

文献信息

• Formal [4 + 1]- and [5 + 1]-Annulation by an S_N2–Conjugate Addition Sequence: Stereoselective Synthesis of Highly Substituted Carbocycles
  作者：Benny Meng Kiat Tong、Hui Chen、Sin Yee Chong、Yi Li Heng、Shunsuke Chiba

  DOI：10.1021/ol301044e

  日期：2012.6.1

  6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of SN2–conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.

  K 2 CO 3介导的6-溴-2-庚酸和7-溴-2-庚酸与活性亚甲基化合物的反应分别通过一系列S N 2-共轭加成反应（分别为[ 4 + 1]-和[5 +1]-环形）以非对映选择性的方式进行。
• Chemoenzymatic Late‐Stage Modifications Enable Downstream Click‐Mediated Fluorescent Tagging of Peptides
  作者：Alessandro Colombano、Luca Dalponte、Sergio Dall'Angelo、Claudia Clemente、Mohannad Idress、Ahmad Ghazal、Wael E. Houssen

  DOI：10.1002/anie.202215979

  日期：——

  suitable for copper-catalyzed azide-alkyne cycloaddition, metathesis, and inverse-electron-demand Diels-Alder (IEDDA) reactions. A 10-mer tryptophan-containing macrocyclic peptide was tailored by AcyF, and the resulting modified peptide was successfully labelled with a tetrazine–fluorescein conjugate by IEDDA.

  用 22 种非天然焦磷酸盐筛选了 N1-色氨酸异戊二烯基转移酶 AcyF 的混杂性，这些焦磷酸盐表现出适合铜催化叠氮-炔环加成、复分解和逆电子需求 Diels-Alder (IEDDA) 反应的反应基团。 AcyF 定制了含有色氨酸的 10 聚体大环肽，并通过 IEDDA 成功地用四嗪-荧光素缀合物标记了所得修饰肽。
• PPAR agonists, compounds, pharmaceutical compositions, and methods of use thereof
  申请人：Mitobridge, Inc.

  公开号：US10188627B2

  公开（公告）日：2019-01-29

  Provided herein are compounds of formula (I) useful for the treatment of PPAR-delta related diseases (e.g. mitochondrial diseases, muscular diseases, vascular diseases, demyelinating diseases and metabolic diseases).

  本文提供的式 (I) 化合物可用于治疗 PPAR-delta 相关疾病（如线粒体疾病、肌肉疾病、血管疾病、脱髓鞘疾病和代谢性疾病）。
• Synthesis of two diastereomers of C-1 ∼ C-14 segment in amphidinolide L
  作者：Jun'ichi Kobayashi、Akiko Hatakeyama、Masashi Tsuda

  DOI：10.1016/s0040-4020(97)10293-9

  日期：1998.1

  In order to determine the stereochemistry of amphidinolide L (1), a cytotoxic macrolide from a marine dinoflagellate, (8S,9S,11R)-2a and (8R,9R,11R)-2b, two diastereomers of the C-1 similar to C-14 segment and (8S,9S,11R)-4a and (8R,9R,11R)-4b, two diastereomers of the C-7 similar to C-14 segment have been synthesized, providing authentic samples for degradation products of 1. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings
  作者：Mark Lautens、Jean-François Paquin、Sandrine Piguel、Marc Dahlmann

  DOI：10.1021/jo0107296

  日期：2001.11.1

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.