1-iodo-2,2-dimethylhexane | 97467-23-7

• 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: 1-iodo-2,2-dimethylhexane
• CAS: 97467-23-7
• 化学式: C₈H₁₇I
• 分子量: 240.127
• InChiKey: YQXZKZLIKSFPSS-UHFFFAOYSA-N

物化性质

• 沸点：
  200.0±8.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• 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：

  1-iodo-2,2-dimethylhexane 在 吡啶 、 氯磺酸 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [2-(4-{4-[3-(2,2-Dimethyl-hexyl)-2-oxo-imidazolidin-1-yl]-benzenesulfonylamino}-phenyl)-ethyl]-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Human β3 andrenergic receptor agonists containing imidazolidinone and imidazolone benzenesulfonamides

  摘要：

  The cyclopentylpropylimidazolidinone L-766,892 is a potent beta(3) AR agonist (EC50 5.7 nM, 64% activation) with 420- and 130-fold selectivity over binding to the beta(1) and beta(2) ARs, respectively. In anesthetized rhesus monkeys, L-766,892 elicited dose-dependent hyperglycerolemia (ED50 0.1 mg/kg) with minimal effects on heart rate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00072-4
• 作为产物：
  描述：

  2,2-二甲基-1-己醇 以65%的产率得到1-iodo-2,2-dimethylhexane
  参考文献：
  名称：

  Convincing Evidence, Not Involving Cyclizable Radical Probes, That the Reaction of LiAlH₄ with Hindered Alkyl Iodides Proceeds Predominantly by a Single Electron Transfer Pathway^,

  摘要：

  Previous workers have maintained that evidence for the radical nature of the reaction of LiAlH4 with sterically hindered alkyl iodides is due to radical initiation by impurities followed by a halogen atom radical chain process involving the cyclizable alkyl iodide probe and that the reduction of the C-I bond actually proceeds by an S(N)2 pathway. In order to resolve the validity of this explanation, 1-iodo-2,2-dimethylhexane (the saturated counterpart of the cyclizable probe), which is not capable of this halogen atom radical chain process, was allowed to react with LiAlD4. The reduction product, 2,2-dimethylhexane, contained only 4-76% deuterium depending on the conditions of the reaction. This result is consistent with the reaction proceeding by a SET process via a radical intermediate and is inconsistent with an S(N)2 pathway. We have determined the influence of the nature of the reaction on the type of reactor surface (Pyrex, Teflon, stainless steel, and quartz) used in the reaction. We have also studied the influence of AlD3 (a byproduct in the reduction) in the mechanistic evaluation of this reaction.

  DOI：

  10.1021/jo961651+

文献信息

• Single electron transfer in the reaction of an alkyl iodide with LiAlH4 and LiAlD4 in the absence of a halogen atom radical chain process
  作者：E.C. Ashby、Catherine O. Welder、Fabio Doctorovich

  DOI：10.1016/s0040-4039(00)79296-3

  日期：1993.11

  Reactions of the noncyclizable alkyl iodide, 1-iodo-2,2-dimethylhexane (9), with LiAlH4 and LiAlD4 have been carried out under a variety of conditions. Although the structure of 9 prohibits a halogen atom radical chain process, deuterium incorporation studies provide convincing evidence for single electron transfer (SET) as the major reaction pathway.

  所述noncyclizable烷基碘的反应中，1-碘-2,2-二甲基己烷（9）中，用的LiAlH 4和LiAlD 4已经在各种条件下进行。尽管9的结构禁止卤素原子自由基链过程，但氘掺入研究为单电子转移（SET）作为主要反应途径提供了令人信服的证据。
• The effect of reactor surfaces on single electron transfer reactions. The reaction of 1-Iodo-2,2-dimethylhexane with lithium aluminum deuteride
  作者：E.C. Ashby、Catherine O. Welder

  DOI：10.1016/0040-4039(95)01486-2

  日期：1995.10

  reactor plays a role in the product distribution. However, treated pyrex, new pyrex and quartz vessels yield consistent data that support single electron transfer as the major reaction pathway in the reduction of 4 with LiAlD4.

  1-碘-2，2-二甲基己烷（4）与LiAlD 4的反应已经在各种反应容器中进行。在用过的派热克斯玻璃纤维，聚四氟乙烯和不锈钢制成的容器中，反应器的表面在产物分布中起作用。但是，经过处理的派热克斯玻璃，新的派热克斯玻璃和石英容器产生的数据一致，支持单电子转移，这是LiAlD 4还原4中的主要反应途径。
• Investigation of the purity of alkali metal diphenylphosphides and their reactions with organic halides. Evidence for single electron transfer
  作者：E. C. Ashby、R. Gurumurthy、R. W. Ridlehuber

  DOI：10.1021/jo00073a051

  日期：1993.10

  For the first time the purity of lithium, sodium, and potassium diphenylphosphide, prepared by various methods, has been evaluated using P-31 NMR spectroscopy. A method was developed to prepare each of the phosphides in a high state of purity. Highly pure potassium diphenylphosphide was then allowed to react with p-iodotoluene in order to determine the effect of purity on the S(RN)1 nature of this reaction. The results were then compared with literature reports which used less pure KPPh2. The mechanism of reaction of alkyl halides with pure alkali metal diphenylphosphides, using the radical probes 6-halo-5,5-dimethyl-1-hexenes and 1-halo-2,2-dimethylhexanes, was investigated. The results provide the first evidence to support single electron transfer (SET) in the reaction of an alkali metal diphenylphosphide with an alkyl halide. SET was found to be the major reaction pathway in the reaction of hindered alkyl iodides (neopentyl type). On the other hand, SET was found to be a minor pathway in the reaction of the corresponding alkyl bromides and chlorides with PPh2-. There was no evidence found for SET in the reactions of unhindered alkyl halides with PPh2- although SET participation cannot be rigorously excluded.
• Competing radical, carbanion, and carbene pathways in the reactions of hindered primary alkyl halides with lithium dialkylamides
  作者：E. C. Ashby、B. Park、G. S. Patil、K. Gadru、R. Gurumurthy

  DOI：10.1021/jo00054a028

  日期：1993.1

  A variety of methods were utilized to study the mechanism of reaction of 6-iodo-5,5-dimethyl-1-hexene and its bromo, chloro, and tosylate derivatives with LDA and several other lithium dialkylamides. In the reaction of 6-iodo-5,5-dimethyl-1-hexene with LDA in THF, radical, carbanion, and carbene pathways occurred simultaneously. However, when the corresponding bromide was allowed to react with LDA, the radical pathway was minor and when the corresponding chloride or tosylate was allowed to react with LDA, no evidence for radical products was observed. This is the first time that competing radical, carbanion, and carbene pathways have been detected in the reaction of a primary alkyl halide with any nucleophile.
• Single electron transfer in the reaction of enolates with alkyl halides
  作者：E. C. Ashby、J. N. Argyropoulos

  DOI：10.1021/jo00218a007

  日期：1985.9