exo-(E)-2-styrylbicyclo(2.2.1)heptane | 76217-04-4

• 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: exo-(E)-2-styrylbicyclo(2.2.1)heptane
• 英文别名: (1R,2R,4S)-2-[(E)-2-phenylethenyl]bicyclo[2.2.1]heptane
• CAS: 76217-04-4
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: NTLYOWXZEJWQJD-HXFZWMNWSA-N

物化性质

• 沸点：
  300.0±9.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  exo-2-bromonorbornane 、 (E)-1-phenyl-(2-tributylstannyl)ethene 在 2,2'-联吡啶 、 potassium tert-butylate 、 nickel dichloride 作用下， 以 异丁醇 、 叔丁醇 为溶剂， 反应 20.0h， 以62%的产率得到exo-(E)-2-styrylbicyclo(2.2.1)heptane
  参考文献：
  名称：

  Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents

  摘要：

  The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2'-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products.

  DOI：

  10.1021/ja0436300

文献信息

• Palladium-catalyzed preparation of exo-aryl derivatives of the norbornane skeleton
  作者：A. Arcadi、F. Marinelli、E. Bernocchi、S. Cacchi、G. Ortar

  DOI：10.1016/0022-328x(89)85320-3

  日期：1989.6

  Norbornene and norbornadiene derivatives have been shown to react with aryl and vinyl halides in the presence of a palladium catalyst, formic acid, and tributylamine or piperidine to give hydroarylated and hydrovinylated derivatives in good to high yield. Extension of the reaction to the hindered α,β-unsaturated aldehydic system of myrtenal produced a monocyclic derivative through a palladium-catalyzed

  已显示降冰片烯和降冰片二烯衍生物在钯催化剂，甲酸，三丁胺或哌啶的存在下与芳基和乙烯基卤化物反应，以良好或高收率得到氢化芳基化和氢化乙烯基化的衍生物。反应扩展到受阻的Myrtenal醛的α，β-不饱和醛体系通过钯催化的开环产生了单环衍生物。
• Monodisperse amorphous CuB₂₃ alloy short nanotubes: novel efficient catalysts for Heck coupling of inactivated alkyl halides and alkenes
  作者：Fan Yang、Shi Yan Fu、Wei Chu、Chun Li、Dong Ge Tong

  DOI：10.1039/c4ra08517e

  日期：——

  Heck-type coupling of inactivated alkyl halides and alkenes, catalyzed by amorphous CuB23 alloy short nanotubes, has been developed. Such couplings occur on the surfaces of nanotubes via a single-electron oxidative reaction. The results indicate that CuB23 nanotubes are efficient catalysts to replace Pd and Ni complexes for such Heck-type coupling.

  已经开发出由非晶态CuB 23合金短纳米管催化的灭活卤代烷和烯烃的Heck型偶联。这种偶联通过单电子氧化反应发生在纳米管的表面上。结果表明，CuB 23纳米管是代替Pd和Ni络合物用于这种Heck型偶联的有效催化剂。
• Palladium-catalysed asymmetric hydroalkenylation of norbornene
  作者：Fumiyuki Ozawa、Yosuhiro Kobatake、Akihiko Kubo、Tamio Hayashi

  DOI：10.1039/c39940001323

  日期：——

  Catalytic asymmetric hydroalkenylation of norbornene (bicyclo[2.2.1]hept-2-ene) can be performed in 93% e.e. using 1-methyl-2-(ethoxycarbonyl)ethenyl triflate 5 as alkenylation agent and Pd(R)-binap}2 as chiral catalyst.

  降冰片烯（双环[2.2.1]庚-2-烯）的催化不对称加氢烯基化可以在 93% e.e. 下进行。使用1-甲基-2-(乙氧基羰基)乙烯基三氟甲磺酸酯5作为烯基化剂和Pd(R)-binap}2作为手性催化剂。