1-bromo-5-(trimethylsilyl)pent-3(Z)-ene | 112129-49-4

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 1-bromo-5-(trimethylsilyl)pent-3(Z)-ene
• 英文别名: (Z)-5-bromopent-2-enyltrimethylsilane；(5-bromopent-2-enyl)trimethylsilane；[(Z)-5-bromopent-2-enyl]-trimethylsilane
• CAS: 112129-49-4
• 化学式: C₈H₁₇BrSi
• 分子量: 221.212
• InChiKey: RKNVDALELPQWIJ-XQRVVYSFSA-N

物化性质

• 沸点：
  213.0±28.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-bromo-5-(trimethylsilyl)pent-3(Z)-ene 在 sodium cyanoborohydride 、 magnesium 作用下， 以 溶剂黄146 为溶剂， 生成 5-((Z)-5-Trimethylsilanyl-pent-3-enyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Esch, Peter M.; Hiemstra, Henk; Klaver, Wim J., Heterocycles, 1987, vol. 26, # 1, p. 75 - 79

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-5-(trimethylsilyl)-3-penten-1-ol 在 三乙胺 、 potassium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-bromo-5-(trimethylsilyl)pent-3(Z)-ene
  参考文献：
  名称：

  Esch, Peter M.; Hiemstra, Henk; Klaver, Wim J., Heterocycles, 1987, vol. 26, # 1, p. 75 - 79

  摘要：

  DOI：

文献信息

• A General Approach to Aza-Heterocycles by Means of Domino Sequences Driven by Hydroformylation
  作者：Etienne Airiau、Thomas Spangenberg、Nicolas Girard、Angèle Schoenfelder、Jessica Salvadori、Maurizio Taddei、André Mann

  DOI：10.1002/chem.200801795

  日期：2008.12.8

  The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

  描述了易于获得的乙烯基乙酰胺的加氢甲酰化多米诺反应的发展。末端双键的极高区域选择性加氢甲酰基化提供了一个瞬态N-酰基，可以被各种亲核试剂捕获，以非对映选择性的方式产生多个氮杂-杂环骨架。
• Reluctant Cross-Metathesis Reactions: The Highly Beneficial Effect of Microwave Irradiation
  作者：Yoann Coquerel、Jean Rodriguez、Antoine Michaut、Thomas Boddaert

  DOI：10.1055/s-2007-983825

  日期：2007.9

  The beneficial effect of microwave irradiation versus classical thermal conditions is demonstrated through a series of comparative cross-metathesis reactions.

  微波辐射相对于传统热条件的有益效果通过一系列比较的交叉转烯反应得以证明。
• Esch, Peter M.; Hiemstra, Henk; Klaver, Wim J., Heterocycles, 1987, vol. 26, # 1, p. 75 - 79
  作者：Esch, Peter M.、Hiemstra, Henk、Klaver, Wim J.、Speckamp, W. Nico

  DOI：——

  日期：——
• The Fluorine Atom as a Cation-Stabilizing Auxiliary in Biomimetic Polyene Cyclizations:  Total Synthesis of <i>dl</i>-Dammarenediol¹
  作者：William S. Johnson、William R. Bartlett、Boris A. Czeskis、Arnaud Gautier、Cheol H. Lee、Rémy Lemoine、Eric J. Leopold、Gregory R. Luedtke、Katherine J. Bancroft

  DOI：10.1021/jo991196s

  日期：1999.12.1

  Dammarenediols I (1a) and II (1b) were prepared by an efficient nonenzymatic biomimetic polyene tetracyclization route. The cyclization substrate, pentaenol 3, contains a tetramethylallylic alcohol initiator, an allyltrimethylsilane terminating group, and a fluorine atom at pro-C-13 to serve as a cation-stabilizing (C-S) auxiliary controlling the regiochemistry of the C/D ring juncture. The synthesis of 3 employed lithium-halogen exchange to create alcohols 10 and 19. The Z-fluoroalkene in 3 was introduced stereoselectively via the Trost palladium-catalyzed alkylation of allylic acetate 11 (Z/E: 4.6/1). The cyclization of 3 was most efficient (62% isolated yield) when it was added as a dilute solution in dichloromethane to trifluoroacetic acid at -45 degrees C to afford tetracyclic fluoro diene 24 possessing the trans-anti-trans-anti-trans ring stereochemistry of the dammaranes. Replacement of the fluorine atom of 24 with hydrogen with complete retention of configuration was accomplished using the Ohsawa-Oishi reagent (Na/K alloy and crown ether). Wacker oxidation of the resulting hydrocarbon provided ketone 28, which after ketalization was ozonolyzed with a reductive workup to give the SP-alcohol 30. Ketal hydrolysis followed by Grignard reaction with isopentenylmagnesium bromide afforded the dammarenediols (1/3, 1a/1b).