1,3-Bis(2'-iodoethyl)benzene | 130800-01-0

• 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: 1,3-Bis(2'-iodoethyl)benzene
• 英文别名: 1,3-bis(2-iodoethyl)benzene；1,3-bis-(2-iodo-ethyl)-benzene；1,3-Bis-(2-jod-aethyl)-benzol
• CAS: 130800-01-0
• 化学式: C₁₀H₁₂I₂
• 分子量: 386.014
• InChiKey: ADAYVHKHEDXXIH-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±35.0 °C(Predicted)
• 密度：
  2.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,3-Bis(2'-iodoethyl)benzene 在 甲烷磺酸 、 乙基溴化镁 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 27.0h， 生成 二苯并[a,j]蒽
  参考文献：
  名称：

  A new general synthesis of polycyclic aromatic compounds based on enamine chemistry

  摘要：

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.

  DOI：

  10.1021/jo00003a050
• 作为产物：
  描述：

  1,3-苯二乙酸 在 lithium aluminium tetrahydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 29.0h， 生成 1,3-Bis(2'-iodoethyl)benzene
  参考文献：
  名称：

  A new general synthesis of polycyclic aromatic compounds based on enamine chemistry

  摘要：

  Alkylation of enamines and enamine salts by benzylic and (beta-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types. Specific polycyclic hydrocarbons synthesized by this route include benzo[a]- and benzo[c]fluorene, 7H-dibenzo[c,g]-, 13H-dibenzo[a,i]-, and 13H-dibenzo[a,g]fluorene, 15H-tribenzo[a,c,i]fluorene, dibenzo[b,def]chrysene, benzo[rst]pentaphene, indeno[1,2-b]fluorene, fluoreno[3,4-c]fluorene, octahydrodibenz[a,j]anthracene, dibenz[a,j]anthracene, octahydrodibenz[a,h]anthracene, dibenz[a,h]anthracene, dibenz[a,h]anthracene, picene, benzo[c]picene, 1H-benz[bc]aceanthrylene, and 4H-cyclopenta[def]chrysene. This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.

  DOI：

  10.1021/jo00003a050

文献信息

• [EN] AEROBIC OXIDATION SYSTEM CONTAINING SULFINIC ACID, SULFONIC ACID OR DERIVATIVES THEREOF AND PHOTOCATALYTIC OXIDATION METHOD THEREFOR<br/>[FR] SYSTÈME D'OXYDATION AÉROBIE CONTENANT DE L'ACIDE SULFINIQUE, DE L'ACIDE SULFONIQUE OU DES DÉRIVÉS ASSOCIÉS ET PROCÉDÉ D'OXYDATION PHOTOCATALYTIQUE CORRESPONDANT<br/>[ZH] 一种含亚磺酸、磺酸或其衍生物的需氧氧化体系及其光促氧化方法
  申请人：UNIV TSINGHUA

  公开号：WO2020155595A1

  公开（公告）日：2020-08-06

  公开了一种需氧氧化体系及其光促需氧氧化方法，该需氧氧化体系包括1)下述物质1a)～1d)的至少一种：1a)亚磺酸或其衍生物；1b)磺酸或其衍生物；1c)通过反应可以生成亚磺酸或其衍生物的化合物或混合物；1d)通过反应可以生成磺酸或其衍生物的化合物或混合物；和2)含分子氧的组分，包括氧气、含氧气的气体和可以原位生成氧分子的反应体系的原料中的至少一种。该需氧氧化体系用于氧化方法时，在光照条件下，无需添加光敏化试剂，室温下即可需氧氧化一系列化合物得到相应的氧化产物，降低了生产成本；另外，所述方法能够大幅度降低能耗，彻底解决由重金属和酸性溶剂带来的废弃物排放污染环境的问题，以及产品中金属残留的问题。
• Synthesis of Potentially Carcinogenic Higher Oxidized Metabolites of Dibenz[<i>a,j</i>]anthracene and Benzo[<i>c</i>]chrysene
  作者：Ronald G. Harvey、Wei Dai、Jin-Tao Zhang、Cecilia Cortez

  DOI：10.1021/jo980415r

  日期：1998.11.1

  Bis(dihydrodiols) and other higher oxidized metabolites are implicated as active carcinogenic metabolites of polycyclic aromatic hydrocarbons, such as dibenz[a,j]anthracene, that possess more than one bay region in the molecule. The bis(dihydrodiol) metabolites may potentially undergo further metabolism to mono- or diepoxides that combine covalently with DNA, or undergo conversion to bis(catechols) that enter into a redox cycle with O-2 to form reactive oxygen species that attack DNA. This paper reports convenient syntheses of the terminal ring bis(dihydrodiol) derivatives of dibenz[a,j]anthracene (5) and benzo[c]chrysene (6) via routes that involve in the key steps double oxidative photocyclization of tetramethaxy-substituted diolefins. The latter are synthesized via double Wittig reaction of a bis(phosphonium) salt with 2,3-dimethoxybenzaldehyde. Demethylation of the bis(catechol) products followed by acetylation and reduction with NaBH4 in the presence of O-2 affords the bis(dihydrodiol) products. Several additional higher oxidized derivatives of dibenz[a,j]anthracene, specifically the 3,11-diphenol (14a), the 11-hydroxy-3,4-quinone (15), and the 11-hydroxy-trans-3,4- dihydro diol (2 c), are obtained by an alternative synthesis entailing the re action of the lithium salt of 1,4-dimethoxy-1,4-cyclohexadiene with 1,3-bis(iodoethyl)benzene to furnish a bis-alkylated diketone which undergoes acid-catalyzed cyclization to 3,1 l-diketododecahydrodibenz[a,j]anthracene.
• Über m-Phenylen-β,β-di-äthylbromid; ein Beitrag zur Desaminierung aliphatischer Diamine. (56. Mitteilung über Stickstoff-Heterocyclen)
  作者：Paul Ruggli、Bernhard Prijs

  DOI：10.1002/hlca.660280197

  日期：——
• HARYEY, RONALD G.;PATAKI, JOHN;CORTEZ, CECILIA;DI, RADDO PASQUALE;YANG, C+, J. ORG. CHEM., 56,(1991) N, C. 1210-1217
  作者：HARYEY, RONALD G.、PATAKI, JOHN、CORTEZ, CECILIA、DI, RADDO PASQUALE、YANG, C+

  DOI：——

  日期：——