1,5-二氯-1,5-二苯基戊烷 | 164297-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二氯-1,5-二苯基戊烷
• 英文名称: 1,5-dichloro-1,5-diphenylpentane
• 英文别名: (1,5-Dichloro-5-phenylpentyl)benzene
• CAS: 164297-87-4
• 化学式: C₁₇H₁₈Cl₂
• 分子量: 293.236
• InChiKey: OQJFAWXRUVDXCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,5-二氯-1,5-二苯基戊烷 在 nickel(II) iodide 、 2,2'-联吡啶 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以40%的产率得到1,2-二苯基环戊烷
  参考文献：
  名称：

  Nickel-Catalyzed Reductive Cyclization of Alkyl Dihalides

  摘要：

  The reductive coupling protocol to intra-molecular cyclization of dihaloalkanes is presented. It leads to five- and six-membered rings, with the former being more efficient. The incorporation of secondary alkyl halides generally promotes coupling, efficiency. To the best of our know ledge this is the first catalytic ring closure reaction arising form dihaloalkanes under chemical reductive conditions.

  DOI：

  10.1021/ol502207z
• 作为产物：
  描述：

  1,5-二苯基戊烷-1,5-二醇 在 盐酸 作用下， 反应 8.0h， 以92%的产率得到1,5-二氯-1,5-二苯基戊烷
  参考文献：
  名称：

  Laser Flash, Laser-Drop, and Preparative Photochemistry of 1,5-Diiodo-1,5-diphenylpentane. Detection of a Hypervalent Iodine Radical Intermediate

  摘要：

  Studies of the laser flash and laser-drop photolysis of 1,5-diiodo-1,5-diphenylpentane (4) support the intermediacy of a cyclic hypervalent iodine radical, 19. Radical 19 has spectroscopic and chemical properties quite different from those of typical benzylic radicals; for example, the absorption spectrum of 19 is red-shifted and significantly broader than that for the 5-chloro-1,5-diphenylpentyl radical, 14. In addition, 19 is virtually unreactive toward oxygen. Laser-drop photolysis of 4 led to further decomposition of 19 to yield primarily a mixture of isomeric 1,2-diphenylcyclopentanes (18) presumably from the corresponding 1,5-biradical. The differences and similarities between this biradical and that produced in the photolysis of 1,5-diphenylcyclohexanone (15) are discussed.

  DOI：

  10.1021/ja00123a006

文献信息

• UV−vis and IR Spectral Characterization of Persistent Carbenium Ions, Generated upon Incorporation of Cinnamyl Alcohols in the Acid Zeolites HZSM-5 and HMor
  作者：Waldemar Adam、Isabel Casades、Vicente Fornés、Hermenegildo García、Oliver Weichold

  DOI：10.1021/jo991801r

  日期：2000.6.1

  detected. No persistent carbocation was observed when the alpha-methylcinnamyl alcohol (2) was incorporated in the acid zeolites, wherein a complete cyclization to 2-methylindene takes place. Finally, incorporation of 2-methyl-4-tolyl-3-buten-2-ol (3) in HZSM-5 allowed detection of the gem-dimethyl-subsituted p-methylcinnamyl cation, with a lifetime of hours. This cation is not persistent enough in HMor

  肉桂醇（1）和两种衍生物2和3已掺入脱水的HMor和HZSM-5沸石中，目的是通过光谱表征固体中产生的相应碳正离子。上清液液相与漫反射紫外可见光谱和红外光谱相结合的产物研究为碳阳离子提供了明确的证据。因此，肉桂醇（1）在HMor和HZSM-5中作为持久性物质提供1,5-二苯基戊二烯基阳离子。在具有较大孔尺寸的HMor的情况下，还可以通过光谱检测到更大的1-（2'-肉桂基）-3-苯基丙烯基阳离子。当将α-甲基肉桂醇（2）掺入酸性沸石中时，未观察到持久的碳正离子化，其中完全环化成2-甲基茚。最后，在HZSM-5中加入2-甲基-4-甲苯基-3-丁烯-2-醇（3）可以检测宝石-二甲基取代的对甲基肉桂基阳离子，使用寿命为数小时。该阳离子在HMor中不够持久，无法表征。本研究表明结构相关的烯丙基底物如何产生不同的碳正离子，其持久性取决于酸性沸石内部的主客体配合。
• Laser Flash, Laser-Drop, and Preparative Photochemistry of 1,5-Diiodo-1,5-diphenylpentane. Detection of a Hypervalent Iodine Radical Intermediate
  作者：J. T. Banks、Hermenegildo Garcia、Miguel A. Miranda、Julia Perez-Prieto、J. C. Scaiano

  DOI：10.1021/ja00123a006

  日期：1995.5

  Studies of the laser flash and laser-drop photolysis of 1,5-diiodo-1,5-diphenylpentane (4) support the intermediacy of a cyclic hypervalent iodine radical, 19. Radical 19 has spectroscopic and chemical properties quite different from those of typical benzylic radicals; for example, the absorption spectrum of 19 is red-shifted and significantly broader than that for the 5-chloro-1,5-diphenylpentyl radical, 14. In addition, 19 is virtually unreactive toward oxygen. Laser-drop photolysis of 4 led to further decomposition of 19 to yield primarily a mixture of isomeric 1,2-diphenylcyclopentanes (18) presumably from the corresponding 1,5-biradical. The differences and similarities between this biradical and that produced in the photolysis of 1,5-diphenylcyclohexanone (15) are discussed.
• Nickel-Catalyzed Reductive Cyclization of Alkyl Dihalides
  作者：Weichao Xue、Hailiang Xu、Zhuye Liang、Qun Qian、Hegui Gong

  DOI：10.1021/ol502207z

  日期：2014.10.3

  The reductive coupling protocol to intra-molecular cyclization of dihaloalkanes is presented. It leads to five- and six-membered rings, with the former being more efficient. The incorporation of secondary alkyl halides generally promotes coupling, efficiency. To the best of our know ledge this is the first catalytic ring closure reaction arising form dihaloalkanes under chemical reductive conditions.
• Lamp <i>versus</i> Laser Photolysis of a Bichromophoric Dichloroalkane:  Chemical Evidence for the Two-Photon Generation of the 1,5-Diphenylpentanediyl Biradical
  作者：Julia Pérez-Prieto、Miguel Angel Miranda、Hermenegildo García、Klára Kónya、J. C. Scaiano

  DOI：10.1021/jo960033q

  日期：1996.1.1

  Low intensity (lamp) photolysis of 1,5-dichloro-1,5-diphenylpentane (1) leads to the formation of the 1-chloro-1,5-diphenylpentyl radical (7) through C-CI bond cleavage. Radical 7 leads to the final products through typical free radical reactions. No cyclopentanes are formed under low intensity conditions. In contrast, high intensity laser irradiation leads to C-Cl photocleavage of radical 7 to yield the 1,5-diphenylpentanediyl biradical (11), which results in the formation of isomeric cis- and trans-1,2-diphenylcyclopentanes; the behavior of these biradicals agrees well with that observed when their precursor is 2,6-diphenylcyclohexanone. Two-color two-laser experiments suggest that both singlet and triplet biradicals are formed, even if only the latter are detectable with nanosecond techniques.