(E)-2-chloro-5-methylhex-3-ene | 68318-04-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: (E)-2-chloro-5-methylhex-3-ene
• 英文别名: 2-chloro-5-methyl-hex-3t-ene；(E)-2-Chlor-5-methyl-3-hexen
• CAS: 68318-04-7
• 化学式: C₇H₁₃Cl
• 分子量: 132.633
• InChiKey: YTIWTBWWIUDXHL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苄烯丙二腈 、 (E)-2-chloro-5-methylhex-3-ene 、 烯丙基三丁基锡 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到5,5-dicyano-6,9-dimethyl-4-phenyldeca-1,7-diene
  参考文献：
  名称：

  Control of the Regioselectivity in Catalytic Transformations Involving Amphiphilic Bis-allylpalladium Intermediates:  Mechanism and Synthetic Applications

  摘要：

  Various dialkyl-substituted allyl chloride derivatives (2d-i) undergo regioselective palladium-catalyzed coupling reactions with allylstannanes (1a,b) and benzylidenemalonitrile (4), providing functionalized 1,7-octadienes in good yield. The catalytic reaction proceeds through an unsymmetrical amphiphilic bis-allylpalladium intermediate. An:introductory electrophilic attack on the terminal position of the unsubstituted alkyl moiety is followed by a nucleophilic attack on the alkyl-substituted allyl ligand. A theoretical analysis was performed by applying density functional theory at the B3PW91/DZ+P level to study the substituent effects on the electrophilic attack. According to the theoretical results, the high regioselectivity can be ascribed to the electronic effects of the alkyl substituents: The terminal alkyl groups destabilize the eta (1),eta (3)-bis-allylpalladium intermediate of the reaction; in addition, the alkyl substitution increases the activation barrier for the electrophilic attack.

  DOI：

  10.1021/jo001374d
• 作为产物：
  描述：

  (E)-5-methylhex-3-en-2-ol 在 吡啶 、 三氯化磷 作用下， 生成 (E)-4-chloro-5-methylhex-2-ene 、 (E)-2-chloro-5-methylhex-3-ene
  参考文献：
  名称：

  Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs

  摘要：

  Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A(1).

  DOI：

  10.1021/ja800103z

文献信息

• Pipette Tip Containing Particle-Filled Polymer Monolith
  申请人：Bonn Alexander

  公开号：US20100009845A1

  公开（公告）日：2010-01-14

  The present invention relates to a pipette tip which is fitted with a porous organic monolith which is doped with active particles. Due to a unique polymerization method, the extraction tips stay highly permeable which allows sample to pass through the monolithic bed. The extraction tip represents an ideal tool for solid phase extraction, especially for desalting, isolating and purifying biomolecules such as peptides and proteins.
• US8105513B2
  申请人：——

  公开号：US8105513B2

  公开（公告）日：2012-01-31
• [DE] VERFAHREN ZUR DETEKTION ORGANISCHER VERBINDUNGEN<br/>[EN] METHOD FOR DETECTING ORGANIC COMPOUNDS<br/>[FR] PROCEDE DE DETECTION DE COMPOSES ORGANIQUES
  申请人：AUSTRIA WIRTSCHAFTSSERV GMBH

  公开号：WO2007030849A1

  公开（公告）日：2007-03-22

  [EN] The invention relates to a method for detecting organic compounds, especially peptides or proteins, in biological sample solutions, comprising the following steps: incubation of the biological sample solutions containing at least one type on the surface of chemically functionalized, substantially spherical cellulose (beads); deposition of the substances remaining in solution from the incubated, functionalized cellulose beads, preferably by centrifugation; application of the incubated, functionalized cellulose beads to a mass spectrometer sample support (target); and analysis of the organic compounds bound to the cellulose beads by way of Matrix Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry (MALDI-TOF MS), the functionalized cellulose beads having an average diameter of < 20 ?m, preferably of approximately 8-10 ?m.
  [FR] L'invention concerne un procédé de détection de composés organiques, notamment de peptides ou protéines, de solutions échantillons biologiques. Ce procédé consiste à incuber les solutions échantillons biologiques avec au moins une sorte de cellulose (billes) sensiblement sphérique et chimiquement fonctionnalisée à la surface ; à séparer les substances, demeurant en solution, des billes cellulosiques incubées, fonctionnalisées, de préférence par centrifugation, application des billes cellulosiques incubées fonctionnalisées sur un support d'échantillon spectromètre de masse (cible) et à analyser les composés organiques liés aux billes cellulosiques par spectrométrie de masse MS désorption/ionisation laser assistée par matrice à temps de vol (MALDI-TOF MS). Les billes cellulosiques fonctionnalisées ont un diamètre moyen < 20 ?m, de préférence d'environ 8-10 ?m.
  [DE] Verfahren zur Detektion organischer Verbindungen, insbesondere Peptide oder Proteine, aus biologischen Probenlösungen, umfassend die Schritte, Inkubation der biologischen Probenlösungen mit wenigstens einer Sorte an der Oberfläche chemisch funktionalisierter, im Wesentlichen kugelförmiger Zellulose (Beads), Abscheiden der in Lösung verbleibenden Substanzen von den inkubierten, funktionanlisierten Zellulose Beads, vorzugsweise durch Zentrifugieren, Aufbringen der inkubierten, funktionanlisierten Zellulose Beads auf einen Massenspektrometer Probenträger (Target) und Analysieren der an die Zellulose Beads gebundenen organischen Verbindungen mittels Matrix Assisted Laser Desorptions-/Ionisation-Time of Flight Mass Spectrometry (MALDI-TOF MS), wobei die funktionalisierten Zellulose-Beads einen mittleren Durchmesser von < 20 µm aufweisen, vorzugsweise von etwa 8-10 µm.
• Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs
  作者：Sunghee Son、Gregory C. Fu

  DOI：10.1021/ja800103z

  日期：2008.3.1

  Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A(1).
• Control of the Regioselectivity in Catalytic Transformations Involving Amphiphilic Bis-allylpalladium Intermediates:  Mechanism and Synthetic Applications
  作者：Niclas Solin、Sanjay Narayan、Kálmán J. Szabó

  DOI：10.1021/jo001374d

  日期：2001.3.1

  Various dialkyl-substituted allyl chloride derivatives (2d-i) undergo regioselective palladium-catalyzed coupling reactions with allylstannanes (1a,b) and benzylidenemalonitrile (4), providing functionalized 1,7-octadienes in good yield. The catalytic reaction proceeds through an unsymmetrical amphiphilic bis-allylpalladium intermediate. An:introductory electrophilic attack on the terminal position of the unsubstituted alkyl moiety is followed by a nucleophilic attack on the alkyl-substituted allyl ligand. A theoretical analysis was performed by applying density functional theory at the B3PW91/DZ+P level to study the substituent effects on the electrophilic attack. According to the theoretical results, the high regioselectivity can be ascribed to the electronic effects of the alkyl substituents: The terminal alkyl groups destabilize the eta (1),eta (3)-bis-allylpalladium intermediate of the reaction; in addition, the alkyl substitution increases the activation barrier for the electrophilic attack.