2-exo-benzyloxynorbornane | 50414-48-7

• 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: 2-exo-benzyloxynorbornane
• 英文别名: 2-exo-benzyloxybicyclo[2.2.1]heptane；exo-2-benzyloxybicyclo[2.2.1]heptane；2-(benzyloxy)bicyclo[2.2.1]heptane
• CAS: 50414-48-7
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: MEQRDIQXHKHFMG-BFHYXJOUSA-N

物化性质

• 沸点：
  279.5±9.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 苯甲醇 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以98%的产率得到2-exo-benzyloxynorbornane
  参考文献：
  名称：

  Copper(ii)-catalysed addition of O–H bonds to norbornene

  摘要：

  Cu(OTf)2是一种廉价且对空气和水分稳定的催化剂，可用于脂肪族和芳香族酸及醇对降冰片烯的O-H加成反应。

  DOI：

  10.1039/b509933a

文献信息

• Stereoselective synthesis of side chain-functionalized tetrahydropyrans from 5-hexenols
  作者：Patrick Fries、Melanie Kim Müller、Jens Hartung

  DOI：10.1016/j.tet.2013.12.019

  日期：2014.2

  products of 6-exo-bromocyclization, as exemplified by synthesis of diastereomerically pure 2,4,6-substituted tetrahydropyrans. The cobalt method extends to intermolecular alkene/alkanol cross-coupling and to multi-component reactions between dimethyl fumarate, CHD, a 5-hexenol, and dioxygen, providing α-tetrahydropyranyl-2-methyl succinates in synthetically useful yields.

  当被氟代钴激活时，分子氧通过氧化环化/自由基官能化级联将5-己醇选择性地转化为2-甲基四氢吡喃的2,6-反式，2,5-反式和2,4-顺式衍生物（ II）在环己-1，4-二烯（CHD）溶液中的双-（β-二酮酮）络合物。溴三氯甲烷和CHD溶液中的好氧5-己烯氧化提供了6-外-溴环化的产物，以非对映体纯的2,4,6-取代的四氢吡喃的合成为例。钴方法扩展到分子间烯烃/链烷醇的交叉偶联以及富马酸二甲酯，CHD，5-己烯醇和双氧之间的多组分反应，从而以合成上有用的产率提供α-四氢吡喃基-2-甲基琥珀酸酯。
• Raskildina, Gulnara Z.; Kazakova, Anna N.; Mikhailova, Natalia N., Revue Roumaine de Chimie, 2014, vol. 59, # 10, p. 811 - 815
  作者：Raskildina, Gulnara Z.、Kazakova, Anna N.、Mikhailova, Natalia N.、Grigor'Eva, Nelly G.、Kutepov, Boris I.、Zlotsky, Simon S.

  DOI：——

  日期：——
• Hidden Brønsted Acid Catalysis: Pathways of Accidental or Deliberate Generation of Triflic Acid from Metal Triflates
  作者：Tuan Thanh Dang、Florian Boeck、Lukas Hintermann

  DOI：10.1021/jo201631x

  日期：2011.11.18

  The generation of a hidden Bronsted acid as a true catalytic species in hydroalkoxylation reactions from metal precatalysts has been clarified in case studies. The mechanism of triflic acid (CF3SO3H or HOTf) generation starting either from AgOTf in 1,2-dichloroethane (DCE) or from a Cp*RuCl2/AgOTf/phosphane combination in toluene has been elucidated. The deliberate and controlled generation of HOTf from AgOTf and cocatalytic amounts of tert-butyl chloride in the cold or from AgOTf in DCE at elevated temperatures results in a hidden Bronsted acid catalyst useful for mechanistic control experiments or for synthetic applications.
• Products of direct hydroalkoxylation of norbornene with alcohols over H-beta zeolite catalyst
  作者：G. Z. Raskil’dina、A. M. Suleimanova、A. N. Kazakova、N. G. Grigor’eva、B. I. Kutepov、S. S. Zlotskii

  DOI：10.1134/s0965544115020164

  日期：2015.3

  The reaction of direct hydroalkoxylation of norbornene in the presence of H-beta zeolite catalyst has been studied. It has been found that the selectivity for exo-alkoxynorbornanes of the reaction of norbornene with monohydric alcohols (saturated, unsaturated, or aromatic) reaches 98% at a conversion of 78-98% of the unsaturated compound. The reaction of norbornene with diols (ethylene glycol and 2-butene-1,4-diol) in the presence of H-beta zeolite affords mono- and diethers, whose yield and ratio can be controlled by varying reaction parameters.