1,8,9,10,11,11-hexachloro-2,3-7,6-endotricyclo[6.2.1.0^2,7]undeca-4,9-diene | 26309-05-7

• 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: 1,8,9,10,11,11-hexachloro-2,3-7,6-endotricyclo[6.2.1.0^2,7]undeca-4,9-diene
• 英文别名: desmethylene aldrin；(1S,2S,7R,8R)-1,8,9,10,11,11-hexachlorotricyclo[6.2.1.02,7]undeca-4,9-diene
• CAS: 26309-05-7
• 化学式: C₁₁H₈Cl₆
• 分子量: 352.903
• InChiKey: NZERHKORBTUGSM-YUMGAWCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  1,8,9,10,11,11-hexachloro-2,3-7,6-endotricyclo[6.2.1.0^2,7]undeca-4,9-diene 在 溴 、 sodium methylate 作用下， 生成 4-Brom-endo-tricyclo<6.2.1.0^2.7>undec-4-en
  参考文献：
  名称：

  Rye,A.R.; Wege,D., Australian Journal of Chemistry, 1974, vol. 27, p. 1943 - 1959

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-环己二烯 、 六氯环戊二烯 在 对叔丁基邻苯二酚 作用下， 以80%的产率得到1,8,9,10,11,11-hexachloro-2,3-7,6-endotricyclo[6.2.1.0^2,7]undeca-4,9-diene
  参考文献：
  名称：

  四环[7.3.1.0 2,8 .0 4,12 ] trideca-5,10-二烯的简并Cope重排

  摘要：

  四环[7.3.1.0 2,8 0.0 4,12 ]十三-5,10-二烯（3）合成的和部分经由可逆配体交换解决在其4 η二烯tfacac -铑（I）配合物10和11与C 2-手性双齿双-[[4（R）-甲基-5（R）-苯基恶唑啉基]甲烷]阴离子。在39 – 57°C之间测量（+）3的Cope重排，将其转换成其镜像。动力学参数表明，这种重排的速率比母体hexa-1,5-二烯的重排速率快10 8倍。保持架混合物3的应变和刚度提供一个解释。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4020(97)00335-9

文献信息

• Cellular Localization of Dieldrin and Structure–Activity Relationship of Dieldrin Analogues in Dopaminergic Cells
  作者：Erin M. G. Allen、Virginia R. Florang、Laurie L. Davenport、Yunden Jinsmaa、Jonathan A. Doorn

  DOI：10.1021/tx300458b

  日期：2013.7.15

  The incidence of Parkinson's disease (PD) correlates with environmental exposure to pesticides, such as the organochlorine insecticide, dieldrin. Previous studies found an increased concentration of the pesticide in the striatal region of the brains of PD patients and also that dieldrin adversely affects cellular processes associated with PD. These processes include mitochondrial function and reactive oxygen species production. However, the mechanism and specific cellular targets responsible for dieldrin-mediated cellular dysfunction and the structural components of dieldrin contributing to its toxicity (toxicophore) have not been fully defined. In order to identify the toxicophore of dieldrin, a structure-activity approach was used, with the toxicity profiles of numerous analogues of dieldrin (including aldrin, endrin, and cis-aldrin diol) assessed in PC6-3 cells. The MTT and lactate dehydrogenase (LDH) assays were used to monitor cell viability and membrane permeability after treatment with each compound. Cellular assays monitoring ROS production and extracellular dopamine metabolite levels were also used. Structure and stereochemistry for dieldrin were found to be very important for toxicity and other end points measured. Small changes in structure for dieldrin (e.g., comparison to the stereoisomer endrin) yielded significant differences in toxicity. Interestingly, the cis-diol metabolite of dieldrin was found to be significantly more toxic than the parent compound. Disruption of dopamine catabolism yielded elevated levels of the neurotoxin, 3,4-dihydroicyphenylacetaldehyde, for many organochlorines. Comparisons of the toxicity profiles for each dieldrin analogue indicated a structure-specific effect important for elucidating the mechanisms of dieldrin neurotoxicity.
• Synthetic studies related to the bird-cage system. III. Derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane, tetracyclo[4.4.0.0.3,9.04,8]decane, and pentacyclo[4.4.0.02,5.03,9.04,8]decane
  作者：R. John Stedman、Libby S. Miller、Larry Denton Davis、John R. E. Hoover

  DOI：10.1021/jo00837a007

  日期：1970.12
• Rye,A.R.; Wege,D., Australian Journal of Chemistry, 1974, vol. 27, p. 1943 - 1959
  作者：Rye,A.R.、Wege,D.

  DOI：——

  日期：——
• Degenerate Cope Rearrangement of Tetracyclo[7.3.1.0 2,8 .0 4,12 ]trideca-5,10-diene
  作者：Wolfram Grimme、Susanne Krauthäuser

  DOI：10.1016/s0040-4020(97)00335-9

  日期：1997.7

  bis-[4(R)-methyl- 5(R)-phenyloxazolinyl]methanide anion. The Cope rearrangment of (+) 3, converting it into its mirror image, is measured between 39 – 57 °C. The kinetic parameters show that the rate of this rearrangement is 108 times faster than that of the parent hexa-1,5-diene. The strain and rigidity of the cage compound 3 provide an explanation. © 1997 Elsevier Science Ltd.

  四环[7.3.1.0 2,8 0.0 4,12 ]十三-5,10-二烯（3）合成的和部分经由可逆配体交换解决在其4 η二烯tfacac -铑（I）配合物10和11与C 2-手性双齿双-[[4（R）-甲基-5（R）-苯基恶唑啉基]甲烷]阴离子。在39 – 57°C之间测量（+）3的Cope重排，将其转换成其镜像。动力学参数表明，这种重排的速率比母体hexa-1,5-二烯的重排速率快10 8倍。保持架混合物3的应变和刚度提供一个解释。©1997爱思唯尔科学有限公司。