1-benzeneselenyl-3-chloropropane | 73090-40-1

• 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-benzeneselenyl-3-chloropropane
• 英文别名: 3-(phenylseleno)propyl chloride；3-chloro-1-(phenylselanyl)propane；3-Chloropropylselanylbenzene
• CAS: 73090-40-1
• 化学式: C₉H₁₁ClSe
• 分子量: 233.599
• InChiKey: VHSPGYRSHHRLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-benzeneselenyl-3-chloropropane 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以77%的产率得到1-iodo-3-(phenylselanyl)propane
  参考文献：
  名称：

  Radical cyclisation onto imidazoles and benzimidazoles

  摘要：

  New synthetic methodology has been developed for the synthesis of [1,2-a]Fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(omega-alkyl) radicals are generated using Bu3SnH from N-(omega-phenylselanyl)aIkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used as the leaving groups in the homolytic substitutions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00104-0
• 作为产物：
  描述：

  硒氰酸苯酯 、 1-溴-3-氯丙烷 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1-benzeneselenyl-3-chloropropane
  参考文献：
  名称：

  Facile oxyselenation of olefins in the presence of copper(II) or copper(I) chloride as catalyst

  摘要：

  DOI：

  10.1021/jo01298a039

文献信息

• Radical cyclisations of imines and hydrazones
  作者：W. Russell Bowman、Peter T. Stephenson、Nicholas K. Terrett、Adrian R. Young

  DOI：10.1016/0040-4020(95)00412-2

  日期：1995.7

  Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH

  sp 3碳中心自由基在亚胺和上的自由基环化为合成5和6元环氮杂环提供了一种新方法。到C = N基团的亲电子碳上的环化和5 exo立体电子选择性是主要的机械参数。使用Bu 3 SnH由苯硒基前体生成C中心自由基中间体。
• Oxidation of alcohols to aldehydes and ketones using selenium ionic liquid
  作者：Xian Yi Cheng、Kang Feng Li、Qiao Jian Wang、Cong Ying Wang、Tao Kai Ying

  DOI：10.1016/j.cclet.2012.05.019

  日期：2012.7

  type of ionic liquid supported selenium reagents were synthesized and found to be an excellent catalyst in the oxidation of alcohols to aldehydes and ketones in the presence of 30% H 2 O 2 . The predictable solubility of ionic liquids allows an easy separation of the oxidation products from the reaction mixture. Furthermore, the oxidation reaction can be carried out using an ionic liquid as the solvent

  摘要合成了一种新型的离子液体负载型硒试剂，在30％H 2 O 2存在下，它是醇氧化为醛和酮的优良催化剂。离子液体的可预测溶解度使氧化产物易于从反应混合物中分离出来。此外，可以使用离子液体作为溶剂来进行氧化反应，并且可以将负载有离子液体的硒试剂再循环并使用四次，而催化性能几乎没有下降。
• One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity
  作者：Vincent Fagan、Sarah Bonham、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1039/c003511d

  日期：——

  Bu3SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).

  介绍了 Bu3SnH/1,1′-偶氮双（环己烷腈）（ACN）介导的咪唑并[5,4-f]苯并咪唑和咪唑并[4,5-f]苯并咪唑的五元、六元和七元双烷基环化反应。所评估的醌衍生物对人类宫颈癌（HeLa）和前列腺癌（DU145）细胞系具有选择性毒性（对正常人细胞系 GM00637 的毒性可忽略不计）。只有 6-氨基咪唑并[5,4-f]苯并咪唑的 Fremy 氧化反应产生了亚氨基醌，它对前列腺癌细胞株（DU145）具有高度特异性。
• Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross‐Coupling with Aromatic Alkenes
  作者：Jordi Aragón、Suyun Sun、David Pascual、Sebastian Jaworski、Julio Lloret‐Fillol

  DOI：10.1002/anie.202114365

  日期：2022.5.16

  The photoredox activation of inert chloroalkanes for the cross-coupling reaction with olefins, with a broad functional group tolerance under mild conditions is presented. By combining UV/Vis spectroscopy, EPR, radical clock and deuterium-labelling experiments, [Ni(Py2Tstacn)]+ is proposed to be catalytically competent to activate the Csp3−Cl bond, forming a free radical, which reacts with the alkene

  介绍了惰性氯代烷烃与烯烃交叉偶联反应的光氧化还原活化，在温和条件下具有广泛的官能团耐受性。通过结合 UV/Vis 光谱、EPR、自由基钟和氘标记实验，[Ni(Py 2 Ts tacn)] +被认为具有催化活性来激活 Csp 3 -Cl 键，形成自由基，与烯烃。
• VEDEJS, E.;EBERLEIN, T. H.;MAZUR, D. J.;MCCLURE, C. K.;PERRY, D. A.;RIGGE+, J. ORG. CHEM., 1986, 51, N 9, 1556-1562
  作者：VEDEJS, E.、EBERLEIN, T. H.、MAZUR, D. J.、MCCLURE, C. K.、PERRY, D. A.、RIGGE+

  DOI：——

  日期：——

表征谱图