1-iodo-3-phenylbicyclo<1.1.1>pentane | 127321-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-iodo-3-phenylbicyclo<1.1.1>pentane
• 英文别名: 1-iodo-3-phenylbicyclo[1.1.1]pentane
• CAS: 127321-10-2
• 化学式: C₁₁H₁₁I
• 分子量: 270.113
• InChiKey: RAWXHWQESFAKNH-UHFFFAOYSA-N

物化性质

• 沸点：
  289.2±39.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1-iodo-3-phenylbicyclo<1.1.1>pentane 在 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 76.17h， 生成 3-氟双环[1.1.1]戊烷-1-甲酸
  参考文献：
  名称：

  双环[1.1.1]戊烷环系统中桥头与桥头相互作用的表现。

  摘要：

  一系列3-卤代双环[1.1.1]戊烷-1-羧酸1（Y = COOH； X = F，Cl，Br，I和CF（3））以及母体化合物1（ Y = COOH，X = H）已经制备，并且已经对其一些性质进行了研究。发现它们与二氟化氙的反应涵盖了广泛的反应性。一方面，氟酸1（Y = COOH，X = F）根本没有明显的反应，而另一方面，溴酸1（Y = COOH，X = Br）和母体化合物1（Y = COOH） ，X = H）发生反应，环系统完全崩解。基于控制中间酰氧基自由基物质寿命的极性动力学和热力学效应，提出了一种可能的解释。羧酸盐1的相对易氧化性（Y = COO（-）； X = H，F，Cl，Br，I，CF（3）和COOCH（3）），如通过循环伏安法测定的其峰值氧化电位值（E（p））所反映的那样，其覆盖范围也很广。这些数据与某些酸1（Y = COOH; X = H，F，Cl和CF（3））的解离常数（

  DOI：

  10.1021/jo982124o
• 作为产物：
  描述：

  3-(甲氧基羰基)二环[1.1.1]戊烷-1-羧酸 在 lead(IV) acetate 、 sodium hydroxide 、 2-碘-1,1,1-三氟乙烷 、 N,N'-二环己基碳二亚胺 作用下， 反应 6.0h， 生成 1-iodo-3-phenylbicyclo<1.1.1>pentane
  参考文献：
  名称：

  Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes

  摘要：

  The synthesis of a wide variety of 1,3-disubstituted bicyclo[1.1.1]pentanes is described, with particular emphasis on the generation of a series of S-X-substituted bicyclo[1.1.1]pentyl bromides required for solvolytic studies. Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes in some instances, transformations were effected via carbanionic-type intermediates.

  DOI：

  10.1021/jo00090a015

文献信息

• Toward a molecular-size tinkertoy construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane
  作者：Piotr Kaszynski、Andrienne C. Friedli、Josef Michl

  DOI：10.1021/ja00028a029

  日期：1992.1

  of [n]staffanes (the oligomers of [1.1.1]propellane n=1-5) functionalized on one or both ends is described,and their properties are summarized. The substituents are -COOCH 3 ,-n-C 4 H 9 ,-C 6 H 5 ,-Br,-I and -SCOCH 3 , and their conversion to others,such as -COOH, -COCH 3 and -SH,is demonstrated. it is proposed that these rod-shaped molecules will be useful in the development of a molecular-size civil

  描述了一种在一端或两端官能化的 [n]staffanes（[1.1.1]propellane 的低聚物 n=1-5）的简便但低场合成，并总结了它们的性质。取代基为-COOCH 3 、-nC 4 H 9 、-C 6 H 5 、-Br、-I 和-SCOCH 3 ，并证明了它们向其他取代基如-COOH、-COCH 3 和-SH 的转化。建议这些棒状分子将有助于开发类似于儿童玩具建筑套装的分子大小的土木工程建筑套装
• Nickel- and Palladium-Catalyzed Cross-Coupling Reactions at the Bridgehead of Bicyclo[1.1.1]pentane Derivatives - A Convenient Access to Liquid Crystalline Compounds Containing Bicyclo[1.1.1]pentane Moieties
  作者：Matthias Messner、Sergei I. Kozhushkov、Armin de Meijere

  DOI：10.1002/1099-0690(200004)2000:7<1137::aid-ejoc1137>3.0.co;2-2

  日期：2000.4

  Pd(PPh3)4, or PdCl2(dppf) catalysis to give a number of 1,3-disubstituted bicyclo[1.1.1]pentyl derivatives 17, 20, and 23, several of which exhibit liquid crystalline properties, in moderate to very good yields. The coupling products 20ca, 23ab, 23ae, 23ff, and 23fg have been further transformed to yield bicyclo[1.1.1]pentyl derivatives 32, 24ab, 24ae, 27ff, and 27fg, respectively, bearing alkynyl, cyano

  有机碘化物 7a-s 在 [1.1.1] 推进烷 (2) 上的自由基加成反应，然后是卤素-锂交换和与氯化锌的金属转移，以及将格利雅试剂添加到 2，提供了各种 3-取代双环[1.1.1]pentyl-1-magnesium (14) 和-zinc (19) 衍生物。后者在 NiCl2dppe、Pd(PPh3)4 或 PdCl2(dppf) 催化下与各种烯基、芳基和联芳基卤化物和三氟甲磺酸酯偶联，得到许多 1,3-二取代的双环 [1.1.1] 戊基衍生物 17 、20和23，其中一些表现出液晶性质，产率中等至非常好。偶联产物 20ca、23ab、23ae、23ff 和 23fg 已进一步转化为双环 [1.1.1] 戊基衍生物 32、24ab、24ae、27ff 和 27fg，分别带有炔基、氰基和/或烯基.
• Formation and Reactions of Bicyclo[1.1.1]pentyl-1 Cations
  作者：Kenneth B. Wiberg、Neil McMurdie

  DOI：10.1021/ja00105a046

  日期：1994.12

  The ionization of l-bicyclo[1.1.1]pentyl halides was shown to initially form the 1,3-bridged bicycle[1.1.1]pentyl-l cation. It appears to be a transition state that leads to the bicyclo[1.1.0]butyl-1-carbinyl cation which can be trapped with azide ion and can be directly observed by NMR in SO2CIF. Although the major products of solvolysis of the halides are 3-methylenecyclobutyl derivatives, the corresponding cation was calculated to have a significantly higher energy than the bicyclobutylcarbinyl ion. Therefore, the products are probably formed by an attack of the nucleophile on the latter ion, accompanied by bond migration. The bridgehead iodide reacts under solvolytic conditions with azide ion to form bicyclo[1.1.0]butyl-l azide as a product. It also reacts with potassium hydroxide to give [1.1.1]propellane, and the same reaction occurs on dissolving in acetonitrile or pyridine. The reaction of 1,3-diiodobicyclo[1.1.1]pentane with ethoxide ion also was found to give [1.1.1]propellane via a nucleophilic attack on one of the iodines. The propellane reacts with methyl hypoiodite to give 3-iodobicyclo[1.1.1]pentyl-l cation, which can react with methanol to give 3-methoxybicyclo[1.1.1]pentyl-l iodide and with azide ion to give 3-iodobicyclo[1.1.1]pentyl-1 azide. These data provide evidence for a discrete 3-iodobicyclo[1.1.1]pentyl-l cation intermediate. The effect of substituents on the rate of solvolysis of bicyclo[1.1.1]pentyl-l iodide was studied. With 3-aryl substituents, a value of rho = -1.7 was found, which is similar to that observed in the solvolysis of 3-arylcyclobutyl tosylates (rho = -1.6). The 3-substituted bicyclopentyl halides usually form the corresponding 3-methylenecyclobutyl cations rather than bicyclo[1.1.0]butyl-1-carbinyl ions, because most substituents will help stabilize the former type of ion.
• Symmetric Bridgehead-to-Bridgehead Coupling of Bicyclo[1.1.1]pentanes and [<i>n</i>]Staffanes
  作者：Ctibor Mazal、Alex J. Paraskos、Josef Michl

  DOI：10.1021/jo971419j

  日期：1998.4.1

  Symmetrical bridgehead-to-bridgehead coupling of bicyclo[1.1.1]pentane cages has been effected in 48-70%, yields by the cuprate oxidation method.
• US5405550A
  申请人：——

  公开号：US5405550A

  公开（公告）日：1995-04-11