1,10,11,12,13,13-hexachlorotricyclo[8.2.1.02.9]trideca-5,11-diene | 10297-21-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,10,11,12,13,13-hexachlorotricyclo[8.2.1.02.9]trideca-5,11-diene
• 英文别名: Dechlorane Plus Monoadduct；(1R,2R,5Z,9S,10S)-1,10,11,12,13,13-hexachlorotricyclo[8.2.1.02,9]trideca-5,11-diene
• CAS: 10297-21-9；135821-04-4
• 化学式: C₁₃H₁₂Cl₆
• 分子量: 380.956
• InChiKey: LHUMZYHABWGTAF-OEWTVGTHSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  153-158 °C(Press: 0.5 Torr)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,10,11,12,13,13-hexachlorotricyclo[8.2.1.02.9]trideca-5,11-diene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以8.4 g的产率得到
  参考文献：
  名称：

  Identification and Determination of Hexachlorocyclopentadienyl- Dibromocyclooctane (HCDBCO) in Residential Indoor Air and Dust: A Previously Unreported Halogenated Flame Retardant in the Environment

  摘要：

  Hexachlorocyclopentadienyl-dibromocyclooctane (HCDBCO, CAS 51936-55-1) has been detected in residential indoor air and indoor dust in Ottawa, Canada. The positive identification of the chemical was based on the interpretation of the mass spectra of the chemical obtained under both electron impact and negative chemical ionization operation modes, as well as through the synthesis of this chemical. This is the first report on the presence of HCDBCO in the environment. Although the levels of HCDBCO in indoor dust, with a geometric mean of 2.7 ng g(-1) and a median of 2.0 ng g(-1) respectively, are generally low compared to those of polybrominated diphenyl ethers (PBDEs) and dechlorane plus, another recently detected flame retardant, high levels of HCDBCO were detected in several dust samples with a maximum level of 93,000 ng g(-1) which is 16 times higher than the maximum level of the structurally related dechlorane plus. On the other hand, levels of HCDBCO in indoor air, with a geometric mean of 70 pg m(-3) and a median of 92 pg m(-3), were higher than those of the major PBDE congeners. The maximum level of HCDBCO found in indoor air was 3000 pg m(-3). Structurally, HCDBCO belongs to a group of norbornane based halogenated flame retardants. The presence of HCDBCO in the indoor environment may raise awareness of the potential release of this and related flame retardants into the environment during the production and usage of products that contain them, and the potential implications of human exposure to these chemicals as people spend the majority of their time indoors in modern society.

  DOI：

  10.1021/es702272s
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 、 六氯环戊二烯 以 二氯甲烷 为溶剂， 反应 1.0h， 以7 g的产率得到1,10,11,12,13,13-hexachlorotricyclo[8.2.1.02.9]trideca-5,11-diene
  参考文献：
  名称：

  Identification and Determination of Hexachlorocyclopentadienyl- Dibromocyclooctane (HCDBCO) in Residential Indoor Air and Dust: A Previously Unreported Halogenated Flame Retardant in the Environment

  摘要：

  Hexachlorocyclopentadienyl-dibromocyclooctane (HCDBCO, CAS 51936-55-1) has been detected in residential indoor air and indoor dust in Ottawa, Canada. The positive identification of the chemical was based on the interpretation of the mass spectra of the chemical obtained under both electron impact and negative chemical ionization operation modes, as well as through the synthesis of this chemical. This is the first report on the presence of HCDBCO in the environment. Although the levels of HCDBCO in indoor dust, with a geometric mean of 2.7 ng g(-1) and a median of 2.0 ng g(-1) respectively, are generally low compared to those of polybrominated diphenyl ethers (PBDEs) and dechlorane plus, another recently detected flame retardant, high levels of HCDBCO were detected in several dust samples with a maximum level of 93,000 ng g(-1) which is 16 times higher than the maximum level of the structurally related dechlorane plus. On the other hand, levels of HCDBCO in indoor air, with a geometric mean of 70 pg m(-3) and a median of 92 pg m(-3), were higher than those of the major PBDE congeners. The maximum level of HCDBCO found in indoor air was 3000 pg m(-3). Structurally, HCDBCO belongs to a group of norbornane based halogenated flame retardants. The presence of HCDBCO in the indoor environment may raise awareness of the potential release of this and related flame retardants into the environment during the production and usage of products that contain them, and the potential implications of human exposure to these chemicals as people spend the majority of their time indoors in modern society.

  DOI：

  10.1021/es702272s

文献信息

• Reverse-electron-demand diels-alder dienophile π-face selectivity via conformation dependent transmission of π-σ-π electronic interactions.
  作者：J.Gabriel Garcia、Mark L. McLaughlin

  DOI：10.1016/s0040-4039(00)92689-3

  日期：1991.7

  Reverse-electron-demand Diels-Alder reactions of a series of remotely substituted cyclooctenes with hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-2,4-diene indicate that dienophile π-face selectivity results from conformation dependent transmission of π-σ-π electronic interactions.

  一系列远程取代的环辛烯与六氯环戊二烯和5,5-二甲氧基-1,2,3,4-四氯环戊-2,4-二烯的反电子需求Diels-Alder反应表明，构象导致了亲二烯体π面选择性π-σ-π电子相互作用的依存传递。
• Identification and Determination of Hexachlorocyclopentadienyl- Dibromocyclooctane (HCDBCO) in Residential Indoor Air and Dust: A Previously Unreported Halogenated Flame Retardant in the Environment
  作者：Jiping Zhu、Yuqing Hou、Yong-lai Feng、Mahiba Shoeib、Tom Harner

  DOI：10.1021/es702272s

  日期：2008.1.1

  Hexachlorocyclopentadienyl-dibromocyclooctane (HCDBCO, CAS 51936-55-1) has been detected in residential indoor air and indoor dust in Ottawa, Canada. The positive identification of the chemical was based on the interpretation of the mass spectra of the chemical obtained under both electron impact and negative chemical ionization operation modes, as well as through the synthesis of this chemical. This is the first report on the presence of HCDBCO in the environment. Although the levels of HCDBCO in indoor dust, with a geometric mean of 2.7 ng g(-1) and a median of 2.0 ng g(-1) respectively, are generally low compared to those of polybrominated diphenyl ethers (PBDEs) and dechlorane plus, another recently detected flame retardant, high levels of HCDBCO were detected in several dust samples with a maximum level of 93,000 ng g(-1) which is 16 times higher than the maximum level of the structurally related dechlorane plus. On the other hand, levels of HCDBCO in indoor air, with a geometric mean of 70 pg m(-3) and a median of 92 pg m(-3), were higher than those of the major PBDE congeners. The maximum level of HCDBCO found in indoor air was 3000 pg m(-3). Structurally, HCDBCO belongs to a group of norbornane based halogenated flame retardants. The presence of HCDBCO in the indoor environment may raise awareness of the potential release of this and related flame retardants into the environment during the production and usage of products that contain them, and the potential implications of human exposure to these chemicals as people spend the majority of their time indoors in modern society.