bornyl bromide | 54825-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bornyl bromide
• 英文别名: (1S,2R,4S)-2-bromo-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 54825-45-5
• 化学式: C₁₀H₁₇Br
• 分子量: 217.149
• InChiKey: OTOQMOVZIUGCQE-QXFUBDJGSA-N

物化性质

• 熔点：
  90 °C
• 沸点：
  80-95 °C(Press: 2 Torr)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  bornyl bromide 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 Petroleum ether 为溶剂， 生成 1,7,7-三甲雙環[2.2.1]庚-2-烯
  参考文献：
  名称：

  Anwendungen der Phasentransfer-Katalyse; 9¹. Neue phasentransfer-katalytische Herstellung von Alkenen aus Alkyl-halogeniden

  摘要：

  DOI：

  10.1055/s-1979-28686

文献信息

• Regiodivergent C−H and Decarboxylative C−C Alkylation by Ruthenium Catalysis: <i>ortho</i> versus <i>meta</i> Position‐Selectivity
  作者：Korkit Korvorapun、Marc Moselage、Julia Struwe、Torben Rogge、Antonis M. Messinis、Lutz Ackermann

  DOI：10.1002/anie.202007144

  日期：2020.10.12

  Ruthenium(II)biscarboxylate complexes enabled the selective alkylation of C−H and C−C bonds at the ortho‐ or meta‐position. ortho‐C−H Alkylations were achieved with 4‐, 5‐ as well as 6‐membered halocycloalkanes. Furthermore, the judicious choice of the directing group allowed for a full control of ortho‐/meta‐selectivities. Detailed mechanistic studies by experiment and computation were performed and

  双羧酸钌(II)配合物能够在邻位或间位选择性烷基化CH和CC键。邻位-C-H烷基化是用4-、5-以及6-元卤代环烷烃实现的。此外，指导小组的明智选择可以完全控制邻位/间位选择性。通过实验和计算进行了详细的机理研究，为邻位烷基化的氧化加成/还原消除过程提供了强有力的支持，而均裂CX裂解可用于间位选择性转化。
• Stereoisomerization of the Bornyl Radical during Aliphatic Nucleophilic Substitutions.
  作者：Kim Daasbjerg、Henning Lund、Carl Erik Olsen、Kim Simonsen、György Liptay、Katrin Trautwein-Fritz、Joseph Stackhouse、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0299

  日期：——

  The mechanism of the reaction between the anion of 4-methoxycarbonyl-1-methyl-1,4-dihydropyridine (1(-)) and endo-2-bromo-1,7,7-trimethylbicyclo[2.2.1]heptane (bornyl bromide) and between 1(-) and exo-2-bromo-1,7,7-trimethylbicyclo[2.2.1]heptane (isobornyl bromide) has been investigated. In both cases the endo and exo substitution products were produced with a small dominance of the inversion product. While the product distribution was independent of temperature for the reaction with bornyl bromide, the yield of the endo-product increased at lower temperatures in the reaction with isobornyl bromide. Clear-cut evidence of a mechanism change in the latter case was not observable in an Arrhenius plot. Different mechanistic interpretations as regards to S(N)2 and electron transfer reactions are discussed.
• Daasbjerg, Kim; Hansen, John N.; Lund, Henning, Acta Chemica Scandinavica, 1990, vol. 44, # 7, p. 711 - 714
  作者：Daasbjerg, Kim、Hansen, John N.、Lund, Henning

  DOI：——

  日期：——