endo-5-ethyl-2-norbornene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: endo-5-ethyl-2-norbornene
• 英文别名: (1R,4R,5S)-5-ethylbicyclo[2.2.1]hept-2-ene
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: QHJIJNGGGLNBNJ-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  endo-5-ethyl-2-norbornene 在 盐酸 、 双氧水 作用下， 以 水 为溶剂， 反应 6.5h， 以85.2%的产率得到3-chloro-5-ethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis of halohydrines of 5-alkylbicyclo[2.2.1]heptene series using the systems inducing electrophilic reagents

  摘要：

  The reactions of induced hydroxyhalogenation of alkylnorbomenes with the use of a mixture of aqueous solutions of hydrochloric or hydrobromic acids (or sodium, potassium and cobalt bromides) and hydrogen peroxide or sodium hypochloriteare are studied. The reaction are established to proceed through the addition at the double bond of the ring of the electrophilic reagent HOBr or HOCl formed in situ yielding of cis-vicinal halohydrines. By dehydrohalogenation of the latter in the presence of alkali are obtained endo-6-alkyl-endo-3-oxatricyclo[3.2.1(1.5).0(2.4)]octanes and by their oxidation are synthesized respective haloketones in a high yield.

  DOI：

  10.1134/s1070363209080192
• 作为产物：
  描述：

  2-(norborn-5-en-2-yl)ethyltoluene-4-sulphonate 在 sodium 、 lithium bromide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 65.0h， 生成 endo-5-ethyl-2-norbornene
  参考文献：
  名称：

  （内基）-5-（2-卤乙基）-2-降冰片烯。一个新的根本探究。

  摘要：

  已经合成了（endo）-5-（2-卤乙基）-2-降冰片烯，并在AIBN存在下与钠，镁，萘钠和氢化三正丁基锡反应生成相应的自由基。和环化产品。该探针的环化速度比常用的5-己烯基卤化物探针快得多。

  DOI：

  10.1016/s0040-4039(01)81431-3

文献信息

• Electrophilic Additions to Ethylidenenorbornene and Vinylnorbornene
  作者：T. C. Shields

  DOI：10.1139/v71-188

  日期：1971.4.1

  Electrophilic and free radical additions to 5-ethylidenebicyclo[2.2.1]hept-2-ene and 5-vinylbicyclo-[2.2.1]hept-2-ene have been carried out with peracetic acid, hydrogen chloride, and methanol. In contrast to chlorosulfonyl isocyanate, peracetic acid primarily attacks the exocyclic double bond in 5-ethylidenebicyclo[2.2.1]hept-2-ene. Several other electrophilic additions are discussed which demonstrate

  5-亚乙基双环[2.2.1]庚-2-烯和5-乙烯基双环-[2.2.1]庚-2-烯的亲电和自由基加成已用过乙酸、氯化氢和甲醇进行。与氯磺酰基异氰酸酯相反，过乙酸主要攻击 5-亚乙基双环[2.2.1]庚-2-烯中的环外双键。讨论了其他几种亲电加成，它们证明了降冰片基系统的不可预测的反应性。
• Organocatalytic synthesis of polysubstituted tetrahydrofurans from alkenes
  作者：Alexis Theodorou、Christoforos G. Kokotos

  DOI：10.1039/c6gc02580c

  日期：——

  A novel, organocatalytic and environmentally friendly protocol for the synthesis of polysubstituted tetrahydrofurans from trivial starting materials is described. Employing a 2,2,2-trifluoroacetophenone-mediated oxidation, which utilizes H2O2 as the green oxidant,...

  描述了一种用于从琐碎的原料合成多取代的四氢呋喃的新颖的，有机催化的和环境友好的方案。采用2,2,2-三氟苯乙酮介导的氧化方法，该方法利用H2O2作为绿色氧化剂，...
• Stereoselectivity in a series of 7-alkylbicyclo[3.2.0]hept-2-enes: Experimental and computational perspectives
  作者：Phyllis Leber、Katherine Kidder、Don Viray、Eric Dietrich-Peterson、Yuan Fang、Alexander Davis

  DOI：10.1002/poc.3888

  日期：2018.12

  decomposition (kd) for a series of exo‐7‐alkylbicyclo[3.2.0]hept‐2‐enes are relatively invariant. For the alkyl substituents ethyl, propyl, butyl, isopropyl, and t‐butyl, the ratio of the rate constant for [1,3] sigmatropic rearrangement to the rate constant for fragmentation, k13/kf, is significantly lower than k13/kf = 150 observed for exo‐7‐methylbicyclo[3.2.0]hept‐2‐ene. Regardless of the size and mass of

  一系列exo -7-烷基双环[3.2.0]庚-2-烯的整体分解速率常数（k d）相对不变。对于烷基取代基乙基，丙基，丁基，异丙基和叔丁基，[1,3]σ重排的速率常数与断裂速率常数的比率k 13 / k f明显低于k 13 / k f  = 150，对于exo -7-甲基双环[3.2.0]庚-2-烯。无论烷基的大小和质量如何，[1,3]碳迁移的立体选择性在表面转化率80％至89％时都相当稳定（si），这与角动量守恒相符，但与轨道对称性守恒相符。总体结果与Carpenter和合作者普遍支持[1,3]σ重排的“动态匹配”现象相对应。
• Further Evidence for the Radical Chain Character of Grignard's Reagent Formation. Use of Free Radical Clock in Conjunction with Changes in Concentration of Active Mg.
  作者：Eric Péralez、Jean-Claude Négrel、Michel Chanon

  DOI：10.1016/0040-4020(95)00814-o

  日期：1995.11

  ratio cyclized / uncyclized increases in the order Cl < Br < I. This ratio decreases when the ratio Mg / RX increases suggesting that the radicals formed by E.T from Mg to RX may be trapped by Mg at a rate competitive with the rate of cyclization of a norbornenyl radical.

  内-5-（2'-卤乙基）-2-降冰片烯（X = I，Br，Cl）与通过金属汽化获得的活性Mg的反应会同时生成环化和未环化的有机镁化合物。环化/未环化的比率按Cl
• Single electron transfer in metal halogen exchange. The reaction of organolithium compounds with alkyl halides
  作者：E. C. Ashby、Tung N. Pham

  DOI：10.1021/jo00383a023

  日期：1987.4