7-iodobicyclo<4.1.0>-heptane | 184641-38-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 7-iodobicyclo<4.1.0>-heptane
• 英文别名: 7-iodonorcarane；endo/exo-7-Iodo-bicyclo<4.1.0>heptan；7-Jodnorcaran；7-Iodobicyclo[4.1.0]heptane
• CAS: 184641-38-1
• 化学式: C₇H₁₁I
• 分子量: 222.069
• InChiKey: QBOFSVLEYBLCAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  8
• 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：

  7-iodobicyclo<4.1.0>-heptane 、 苯乙酮 以0%的产率得到
  参考文献：
  名称：

  Nazareno Monica A., Rossi Roberto A., Tetrahedron, 50 (1994) N 31, S 9267-9274

  摘要：

  DOI：
• 作为产物：
  描述：

  碘仿 、 环己烯 在 碘 、 铜 作用下， 以 苯 为溶剂， 生成 7-iodobicyclo<4.1.0>-heptane
  参考文献：
  名称：

  通过与三卤甲烷和铜反应从烯烃合成一卤代环丙烷衍生物

  摘要：

  在烯烃存在下，通过FCHI 2，ClCHI 2，BrCHI 2和CHI 3分别与Cu反应，可以以10-80％的产率获得氟代，氯代，溴代和碘代环丙烷衍生物。该反应是亲电的，并且立体定向地进行，即，顺式和反式烯烃提供环丙烷衍生物，其相对于来自原始烯烃的取代基的构型为顺式和反式。， 分别。由于在反应混合物中未检测到异构烯烃，这是通过将相应的游离单卤代碳烯插入CH键所预期的，因此该反应似乎是通过有机铜中间体而不是游离的单卤代碳烯进行的。关于通过新反应引入的卤素的构型，通常主要在相应的反式或外型异构体上获得顺式或内式异构体。

  DOI：

  10.1016/0040-4020(79)85049-8

文献信息

• S_RN1 Reactions of 7-Iodobicyclo[4.1.0]heptane, 1-Iodoadamantane, and Neopentyl Iodide with Carbanions Induced by FeBr₂ in DMSO
  作者：Mónica A. Nazareno、Roberto A. Rossi

  DOI：10.1021/jo9509566

  日期：1996.1.1

  of nitromethane (7) was 6.5 times more reactive than 2 toward 7-norcaranyl radicals. The reactions of 1-iodoadamantane (9) and neopentyl iodide (11) with carbanion 2 induced by FeBr(2) gave the substitution products in 85% and 92% yields, respectively. These observations indicate that all these reactions induced by FeBr(2) occur by the S(RN)1 mechanism.

  在25℃下，DMSO中没有7-碘二环[4.1.0]庚烷（7-碘代戊烷，1）（内-外比为约1）与苯乙酮烯醇酸根离子2反应。但是，在相同的实验条件下，添加SmI（2）或FeBr（2），则分别以9％和72％的产率获得取代产物3，其exo-endo比率约为ca。16与光刺激反应的产物比率相似。因此，似乎7-去甲烷基是这些反应的中间体。在60摄氏度下使用FeBr（2），其3的产率高达90％。1与FeBr（2）诱导的2-萘基甲基酮4的烯醇离子的反应以60％的收率（96％的外向异构体）产生取代产物5。在竞争实验中，4是2的1.7倍，而硝基甲烷（7）的阴离子是6。对2-7-正戊烷自由基的反应活性是2的5倍。1-碘金刚烷（9）和新戊基碘（11）与FeBr（2）诱导的碳2的反应分别得到85％和92％的取代产物。这些观察结果表明，FeBr（2）诱导的所有这些反应都是通过S（RN）1机制发生的。
• SRN1 reactions of 7-iodobicyclo[4.1.0]heptane with carbanions. A novel stereoselective CC bond formation on cyclopropane rings
  作者：Mónica A. Nazareno、Roberto A. Rossi

  DOI：10.1016/s0040-4020(01)85504-6

  日期：——

  The photostimulated reaction of 7-iodobicyclo[4.1.0]-heptane (7-iodonorcarane, 1, a mixture of ca. 1:1 of the exo:endo isomers) with acetophenone enolate ion 2 in DMSO at 60 degrees C gave the substitution products 3a (exo) and 3b (endo) in 87% yield (with an exo:endo ratio of 16). In the dark at 60 degrees C, not only the ipso substitution products 3a and 3b (51%), but also the cine substitution product 4 were formed (20%) by an elimination-addition reaction. In the dark and at room temperature there is no reaction. It is suggested that 1 reacts with 2 by a photostimulated as well as a thermal (60 degrees C) S(RN)1 reaction to give the ipso products 3, with a 3a:3b ratio of ca. 15-23, showing a stereoselectivity of the 7-norcaranyl radicals in the coupling reaction with 2. More selectivity of 1 and 2 was found in the photostimulated reaction in liquid ammonia (at -33 degrees C), with a 3a:3b ratio of ca. 55, although in lower yields (37%). The photostimulated reaction of 1 with 2-acetonaphthone 7 gave only the ipso products (with an exo:endo ratio of 45) and in dark conditions at 60 degrees C there is no reaction with 7. There was no photostimulated reaction of 1 with the anion of nitromethane 9 in DMSO. However, the photostimulated reaction of 1 with 9 in presence of acetone enolate ion 10, the ipso substitution products derived from 9 were formed (entrainment S(RN)1 reaction), with an exo:endo ratio of ca. 7.3. From competition experiments, 9 was ca. 6.4 times more reaction than 2.