isodrin | 465-73-6

• 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: isodrin
• 英文别名: isodrine；Isodrin (insecticide)；(1R,2R,3S,6R,7S,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
• CAS: 465-73-6
• 化学式: C₁₂H₈Cl₆
• 分子量: 364.914
• InChiKey: QBYJBZPUGVGKQQ-DIFDVCDBSA-N

物化性质

• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

当异狄林与从菜豆幼苗（菜豆）切除的根部制备的匀浆一起孵化时...观察到与狄林酮（Δ-酮狄林）相对应的色谱化合物。检测到第二种代谢物，含量非常少，但未鉴定。未发现狄林。

When isodrin was incubated with homogenates from excised roots of bean seedlings (phaseolus vulgaris) ... cmpd corresponding chromatographically to endrin ketone (delta-keto endrin) was observed. A second metabolite, present in very small amt, observed, but not identified. No endrin was found.

来源:Hazardous Substances Data Bank (HSDB)

代谢

...异狄氏剂...通过兔肝微粒体转化为狄氏剂。显然，这个酶系统不会对产物狄氏剂进行进一步代谢。

... Isodrin ... is converted to endrin by rabbit liver microsomes. Apparently no further metabolism of the product endrin occurs with this enzyme system.

来源:Hazardous Substances Data Bank (HSDB)

代谢

...的转化在易感和抗性家蝇品系中都已得到证实。用异狄氏剂和恩滴林进行局部处理的易感和抗性家蝇含有少量的水溶性物质（施用剂量的3-4%），这种物质似乎与半笼状酮衍生物相同...这是已知的恩滴林重排产物。

Conversion of isodrin to endrin ... has been demonstrated in both susceptible & resistant strains of houseflies. ... Susceptible & resistant flies topically treated with isodrin & endrin contained small ... amt (3-4% of applied dose) of water sol substance that appeared to be identical to the semi-caged keto derivative ... /which is/ known rearrangement product of endrin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在将14C标记的异狄林（1毫克/株）施用到幼嫩白菜叶片后，4周内在植物和土壤中回收了44%的施用放射性，10周后回收了37%。10周后，只有异狄林的转化产物作为残留物被检测到。在土壤中施用14C异狄林（0.19 ppm）后，胡萝卜在4周后仅含有3.1%的施用放射性，12周后含有4.0%。在这两个实验中，恩德林和 delta-酮恩德林被识别为异狄林的转化产物。

After application of (14)C labeled isodrin (1 mg/plant) to leaves of young white cabbage, 44% of the applied radioactivity was recovered in the plants & soil after 4 wk, & 37% after 10 wk. After 10 wk only conversion products of isodrin were detectable as residues. After application of (14)C isodrin to soil (0.19 ppm), carrots contained only 3.1% of the applied radioactivity after 4 wk & 4.0% after 12 wk. In both experiments, endrin and delta ketoendrin were identified as conversion products of isodrin.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒物 - 有机氯

Other Poison - Organochlorine

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

家蝇将异菌毒代谢成完菌毒。芝麻酚起到了增效作用。

Houseflies metabolized isodrin to endrin. Sesamex acted as a synergist.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。密切观察呼吸不足的迹象，并在必要时协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。预期可能出现癫痫，减少所有外部刺激，并在必要时进行治疗...。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛...。不要使用催吐剂。对于摄入，如果患者能够吞咽，有强烈的干呕反射，并且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭...。/艾氏剂、狄氏剂、恩氏剂及相关化合物/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures, reduce all external stimuli, and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aldrin, dieldrin, endrin, and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于昏迷或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。监测心率和必要时治疗心律失常。开始静脉输注D5W/SRP：“保持通路开放”，最低流速。如果出现低血容量的迹象，使用0.9%盐水（NS）或乳酸林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象。用地西泮或劳拉西泮治疗癫痫。使用丙美卡因，盐酸以协助眼部冲洗。/艾氏剂、狄氏剂、恩氏剂及相关化合物/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... Treat seizures with diazepam or lorazepam ... . Use proparacaine, hydrochloride to assist eye irrigation ... . /Aldrin, dieldrin, endrin, and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

观察。任何途径接触高浓度有机氯杀虫剂的人员应被监测是否有感觉异常、动作不协调、言语含糊、精神异常和不自主的肌肉活动，这些症状可能预示即将发生癫痫。/固体有机氯杀虫剂/

Observation. Persons exposed to high levels of organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. /Solid organochlorine insecticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

从哺乳动物研究中发现，与阿德灵和狄尔德林相比，异德灵和恩德灵中未氯化降冰片烯核的倒置使这个环在体内暴露于酶促羟基化，大大增加了这些化合物从哺乳动物组织中消除的速率，这与它们在昆虫组织中的行为形成对比。

... From mammalian studies that the inversion of the unchlorinated norbornene nucleus in isodrin and endrin (as compared with aldrin and dieldrin) exposes this ring to enzymatic hydroxylation in vivo and greatly incr the rate of elimination of these cmpd from mammalian tissues, in contrast to their behavior in insect tissues.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

合成制备方法

暂无相关信息。

用途

暂无相关信息。

反应信息

• 作为反应物：
  描述：

  isodrin 在 palladium on activated charcoal 、 硫酸 、 sodium 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丁酮 、 xylene 、 叔丁醇 为溶剂， 反应 117.5h， 生成 (1α,2β,3α,6α,7β,8α,9α,14α)-4,5-Benzopentacyclo<6.6.1.1.^3,6.0^2,7.0^9,14>hexadec-4-ene
  参考文献：
  名称：

  "Pagodane": the efficient synthesis of a novel, versatile molecular framework

  摘要：

  DOI：

  10.1021/ja00249a029
• 作为产物：
  描述：

  2,5-降冰片二烯 、 六氯环戊二烯 生成 aldrin 、 isodrin
  参考文献：
  名称：

  六氯环戊二烯与7-取代的降冰片二烯的环加成：远程取代基对反应性和立体选择性的影响

  摘要：

  已经测量了六氯环戊二烯与在7位被-丁基，三甲基甲硅烷基，甲氧基，乙酰氧基，羟基，甲氧基甲基和甲氧基羰基取代的降冰片二烯的环加成率和立体选择性。速率与取代基电负性相关。

  DOI：

  10.1016/s0040-4039(00)88545-7

文献信息

• Rigid face-to-face [3.3]-oo′-cyclophanes arene/alkene and arene/arene photocycloaddition reactions
  作者：Regina Thiergardt、Manfred Keller、Markus Wollenweber、Horst Prinzbach

  DOI：10.1016/s0040-4039(00)79165-9

  日期：1993.5

  Proximity as origin of unusual photoreactivity is being explored: In the naphtho/ene 5 (X-ray analysis), direct or sensitized photoexcitation induce an efficient meta-addition to the naphthalene nucleus; ortho-(2,3)-addition is not enforced. Naphtho/benzo cyclophane 10, however, is photochemically “inert”. Structurally related benzo/enes 4 and 17 undergo photoequilibration (2:1) with the respective

  人们正在探索将近邻作为异常光反应性的起源：在萘/烯5（X射线分析）中，直接或敏化的光激发会引起萘核的有效间加。邻域-（2,3）-加法未强制执行。然而，萘酚/苯并环烷10是光化学上“惰性的”。与结构相关的苯并/烯4和17与各自的[6 + 2]-环加合物进行光平衡（2：1）。
• Intramolecular 2H Group-Transfer (Dyotropic Rearrangements) in Alicyclic and Heterocyclic Bridged-Ring Systems11Preliminary comnunication: K. Mackenzie, G.J. Proctor and D.J. Woodnutt, Tetrahedron Letters 1984, 977.
  作者：K. Mackenzie、G. Proctor、D.J. Woodnutt

  DOI：10.1016/s0040-4020(01)87804-2

  日期：——

  Examples of alicyclic frameworks containing a cyclohexa-1,3-diene ring as 2H donor held proximate to a variously-substituted acceptor Π-bond are compared for their reactivity in thermal 2H group-transfer reactions. Kinetic analysis reveals marked effects on rearrangement-rate as the acceptor Π-bond substieuents are varied. Attempted synthesis of exact structural analogues of these compounds but with

  比较了在2H基团热转移反应中它们的反应性，比较了脂环骨架的实例，该脂环骨架的例子是将环己-1,3-二烯环作为2H供体，其紧邻各种取代的受体Π键。动力学分析表明，随着受体-键取代基的变化，对重排率有显着影响。尝试合成这些化合物的确切结构类似物，但用2,3-二氮杂环己二烯组分代替环己二烯元素[通过3,6-二芳基-1,2：4,5-四嗪的（4 + 2）Π环加成反应生成二烯亲二烯体]通常使用[异狄氏剂型]来产生伴随2H基团转移的产物。将这些结果与具有相关的关键立体化学特征的五环2-吡唑啉衍生物的相似但通常较慢的2H基团转移重排进行了比较，这些衍生自1，异狄氏剂类型的偶极亲和性的3-二芳基硝化胺（4 + 2）Π加合物。在所研究的脂环族和杂环代表性体系中，受体-键的烷氧基和氯取代均会延迟2H基团的转移，这表明了其真正的周环行为。
• Dechlorination Reactions of Hexachlorinated Polycyclic Compounds Using Ultra-Sound Radiation
  作者：Valentim Emilio Uberti Costa、Maria E. S. Möllmann、Valéria Belli Riatto

  DOI：10.1080/00397919508015890

  日期：1995.7

  Abstract Dechlorination reactions of exo-endo and endo-endo perhalogenated tetracyclic compounds with Li/t-BuOH/THF system, when subjected to simultaneous ultra-sound irradiation, led to exceptionally high yields (77-95%) of the corresponding hydrocarbons.

  摘要 外-内和内-内全卤代四环化合物与 Li/t-BuOH/THF 体系的脱氯反应，在同时进行超声辐照时，相应的碳氢化合物的产率非常高（77-95%）。
• Dehalogenation of isodrin and aldrin with alkoxide bases
  作者：C. H. M. Adams、K. Mackenzie

  DOI：10.1039/j39690000480

  日期：——

  Earlier reports suggest that isodrin and aldrin and their derivatives are unreactive towards, e.g., sodium methoxide. The present work describes the largely stereospecific dechlorination of isodrin and aldrin and related fused polychloro-norbornenes with sodium methoxide in methanol–dimethyl sulphoxide. The stereochemistry of the products is established and a unique long-range 1H n.m.r. coupling over

  此前有报道表明，异艾和艾氏剂及其衍生物是对，反应性例如，甲醇钠。目前的工作描述了在甲醇-二甲亚砜中用甲醇钠对异狄氏剂和艾氏剂以及相关的稠合多氯降冰片烯进行立体定向的大部分脱氯。建立了产物的立体化学，并在相关系统中报道了在六个键上的独特的长距离1 H nmr偶联。
• The reaction of aldrin, photoaldrin and isodrin with phthaloyl peroxide
  作者：C.W. Bird

  DOI：10.1016/0040-4020(80)80031-7

  日期：1980.1

  The reactions of aldrin and photoaldrin with phthaloyl peroxide in carbon tetrachloride provided the respective carbon tetrachloride adducts, epoxides and cyclic phthalates of the corresponding cis-diols.

  艾氏剂和光艾氏剂与邻苯二甲酰在四氯化碳中的反应提供了相应的顺式二醇的各自的四氯化碳加合物，环氧化物和环状邻苯二甲酸酯。