1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯 | 3424-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯
• 中文别名: 1,2,3,3,5,5-六氯-4-(二氯亚甲基)环戊烯
• 英文名称: 1,2,3,3,5,5-Hexachloro-4-dichloromethylene-cyclopentene
• 英文别名: 4-dichloromethylene-1,2,3,3,5,5-hexachlorocyclo-1-pentene；1,2,3,3,5,5-hexachloro-4-(dichloromethylene)cyclopentene；2,5-dichlorohexachlorofulvene；hexachloro-4-dichloromethylene-cyclopentene；Hexachlor-4-dichlormethylen-cyclopenten；octachloro-1-methyliden-cyclopent-3-ene；Cyclopentene, 4-(dichloromethylene)-1,2,3,3,5,5-hexachloro-；1,2,3,3,5,5-hexachloro-4-(dichloromethylidene)cyclopentene
• CAS: 3424-05-3
• 化学式: C₆Cl₈
• 分子量: 355.69
• InChiKey: HSNOZNMQZFGXDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  14
• 可旋转键数：
  0
• 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

安全信息

• 海关编码：
  2903890090

反应信息

• 作为反应物：
  描述：

  1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯 在 aluminum tri-bromide 、 硝酸 作用下， 生成 4-bromo-5-chloro-2-dibromomethylene-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Bromination of 1,2,3,3,5,5-Hexachloro-4-(dichloromethylene)-cyclopentene

  摘要：

  DOI：

  10.1021/ja01583a067
• 作为产物：
  描述：

  异辛烷 在 aluminum oxide 、 nickel dichloride 氯 作用下， 生成 1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯
  参考文献：
  名称：

  Hoever,H., Chemische Berichte, 1967, vol. 100, p. 456 - 463

  摘要：

  DOI：
• 作为试剂：
  描述：

  octachlorohexa-1,3,5-triene 在 1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯 、 氯 作用下， 反应 5.25h， 生成 1,2,3,3,5,5-六氯-4-(二氯甲基亚基)环戊烯
  参考文献：
  名称：

  在三个连续的重排中将全氯己三烯异构化为全氯-2-乙烯基丁二烯

  摘要：

  全氯己三烯在三个随后的重排中异构化为全氯-2-乙烯基丁二烯。自由基诱导的线性全氯己三烯Z - E平衡，然后环化为亚甲基环戊烯。在闪蒸热解条件下， 一种发生环收缩为1，2-二亚甲基环丁烷。在浓缩阶段， 一种自由基诱导的开环产生支链的全氯乙烯基丁二烯。所有化合物都只能在非常高的温度下转化为六氯苯。

  DOI：

  10.1016/j.tetlet.2017.01.040

文献信息

• Is Obsessive-Compulsive Disorder Caused by a Second-Messenger Imbalance?
  作者：Donatella Marazziti、Jorge Perez、Giovanni B. Cassano

  DOI：10.1017/s1092852900008579

  日期：2001.3

  Although the precise etiologic nature of obsessive-compulsive disorder (OCD), one of the most common psychiatric conditions, is unknown, several findings indicate involvement of the serotonin (5-HT) transporter. Apart from the specific effects of selective 5-HT reuptake inhibitors, other studies show decreased functionality of the platelet 5-HT transporter in OCD. In this report, the authors combine data from two independent studies of patients with OCD, showing both an increased activity of protein kinase type C (PKC) and a decreased activity of protein kinase type A (PKA). The authors propose a unifying hypothesis that OCD might be determined by an imbalance between PKC and PKA, with a prevalence of the former and, more generally, of the phosphoinositide over the cyclic adenosine monophosphate (cAMP) pathway. Should this hypothesis prove correct, the path would be open for new therapeutic interventions in the treatment of OCD.

  摘要 虽然强迫症（最常见的精神疾病之一）的确切病因尚不清楚，但一些研究结果表明它与血清素（5-HT）转运体有关。除了选择性 5-HT 再摄取抑制剂的特殊作用外，其他研究显示强迫症患者血小板 5-HT 转运体的功能降低。在这份报告中，作者综合了两项针对强迫症患者的独立研究数据，结果显示 C 型蛋白激酶（PKC）的活性增加，而 A 型蛋白激酶（PKA）的活性降低。作者提出了一个统一的假设，即强迫症可能是由 PKC 和 PKA 之间的失衡决定的，前者占主导地位，更广泛地说，磷脂酰肌醇比环磷酸腺苷（cAMP）途径占主导地位。如果这一假说被证明是正确的，那么治疗强迫症的新疗法干预措施就会出现。
• Dentin Matrix Protein 1, a Target Molecule for Cbfa1 in Bone, Is a Unique Bone Marker Gene
  作者：Jian Q. Feng、Jianghong Zhang、Sarah L. Dallas、Yongbo Lu、Shuo Chen、Xiaoyu Tan、Michael Owen、Stephen E. Harris、Mary Macdougall

  DOI：10.1359/jbmr.2002.17.10.1822

  日期：——

  Dentin matrix protein 1 (Dmp1), a phosphoprotein highly linked to dentin formation, has also been reported to be expressed in the skeleton. However, the role of Dmp1 in skeletal tissues remains unclear. To clarify the role of Dmp1 in bone formation, we characterized the expression profile of Dmp1 in bone and cartilage and examined whether Dmp1 expression was regulated by core‐binding factor a1 (Cbfa1). Studies of fetal rat calvarial (FRC) cell cultures showed that the expression of Dmp1 was associated closely with “bone nodule” formation and mineralization in vitro. In situ hybridization studies were performed to examine the spatial and temporal expression patterns of Dmp1 during development in mouse embryos from 12.5 day postcoitus (dpc) to 8 weeks postnatal; these studies showed that Dmp1 first appeared in hypertrophic cartilage cells, followed by osteoblasts, and later was expressed strongly in osteocytes. The expression profiles of Cbfa1 and Dmp1 overlapped in both cartilage and bone during development, with Cbfa1 preceding Dmp1. Examination of Dmp1 expression in Cbfa1−/− mice revealed that Dmp1 was absent in the developing bones of Cbfa1‐null mice, whereas there was essentially no change in Dmp1 expression in the arrested tooth bud. Transient transfection studies showed forced expression of Dmp1 under the control of Cbfa1 and gel shift data indicated the presence of a functional osteocalcin‐specific element (OSE)‐2 response element in the Dmp1 proximal promoter region. However, in vitro promoter studies suggested that regulation of Dmp1 by Cbfa1 was not mediated by direct binding of Cbfa1 to this site and may be through indirect mechanisms. These studies highlight Dmp1 as a unique marker gene for osteoblastic differentiation. The close association of Dmp1 and Cbfa1 in the developing skeleton suggests that Dmp1 may play an important role in bone formation.

  牙本质基质蛋白1（Dmp1）是一种与牙本质形成高度相关的磷蛋白，据报道，它也存在于骨骼中。然而，Dmp1在骨骼组织中的作用尚不清楚。为了阐明Dmp1在骨形成中的作用，我们分析了Dmp1在骨骼和软骨中的表达特征，并研究了Dmp1的表达是否受核心结合因子a1（Cbfa1）的调控。对胎鼠颅骨（FRC）细胞培养的研究表明，Dmp1的表达与“骨结节”的形成和体外矿化密切相关。为了研究小鼠胚胎从交配后12.5天（dpc）到出生后8周发育过程中的时空表达模式，我们进行了原位杂交研究；这些研究表明，Dmp1首先出现在肥厚软骨细胞中，随后出现在成骨细胞中，最后在骨细胞中强烈表达。在发育过程中，Cbfa1和Dmp1在软骨和骨骼中的表达特征重叠，Cbfa1先于Dmp1。对Cbfa1 −/−小鼠中Dmp1表达的研究表明，在Cbfa1 −/−小鼠发育中的骨骼中不存在Dmp1，而在停滞的牙芽中Dmp1的表达几乎没有变化。瞬时转染研究表明，在Cbfa1的调控下，Dmp1被强制表达，凝胶迁移数据显示，在Dmp1近端启动子区域
• Synthesis of Decachloro-4-allylidenecyclopentene and Its Chemistry
  作者：Kousuke Kusuda、Alfred Roedig

  DOI：10.1246/bcsj.52.811

  日期：1979.3

  of anhydrous aluminium chloride. Hexachloro-2-allylidene-4-cyclopentene-1,3-dione (11), prepared from 6 by treatment with coned nitric acid, cyclized to hexachloro-2,5-dihydrocyclopenta[b]pyran-5-one (14) on heating. In a solvent such as acetone and acetonitrile, 4 rearranged to hexachloro-2,5-dihydrocyclopenta[b]pyran-2-one (18) at room temperature. The mechanism of this rearrangement is discussed

  在无水氯化铝存在下，五氯环戊二烯与六氯丙烯反应合成十氯-4-烯丙基环戊烯 (6)。Hexachloro-2-allylidene-4-cyclopentene-1,3-dione (11)，由 6 通过用浓硝酸处理制备，在反应器上环化为六氯-2,5-dihydrocyclopenta[b]pyran-5-one (14)加热。在丙酮和乙腈等溶剂中，4在室温下重排为六氯-2,5-二氢环戊二烯并[b]吡喃-2-酮(18)。讨论了这种重排的机制。14 用 90% 硫酸水解得到四氯-2,5-二氢环戊二酮 [b] 吡喃-2,5-二酮 (15)，它是通过用硫酸处理直接从 6 获得的。研究了 11 与无水甲醇和 15 与重氮甲烷的反应。
• Comments on reactions of oxide derivatives of uranium with hexachloropropene to give UCl₄
  作者：Dipti Patel、Ashley J. Wooles、Emtithal Hashem、Harrison Omorodion、Robert J. Baker、Stephen T. Liddle

  DOI：10.1039/c5nj00476d

  日期：——

  The reactions of U₃O₈, UO₂(NO₃)₂·6H₂O, and UO₂Cl₂ with hexachloropropene to make UCl₄ are described.

  描述了U3O8、UO2(NO3)2·6H2O和UO2Cl2与六氯丙烯反应以制备UCl4。
• Thermal Rearrangements of Perchlorohexatrienes-Structures and Experimental and Theoretical Evaluation of Pathways to Isomerization and Cyclization
  作者：Heiner Detert、Dieter Lenoir、Hendrik Zipse

  DOI：10.1002/ejoc.200801076

  日期：2009.3

  2 kJ mol–1. Unimolecular cis/trans isomerization is predicted to occur through an unusual vinylcyclobutene intermediate 7, whose formation faces a barrier of more than 150 kJ mol–1, but whose stability is comparable to that of 1 and 2. The isomerization rate is strongly enhanced by the addition of small amounts of Br2 or Cl2 or by 3 and can be explained by a radical-induced isomerization mechanism.

  我们已经通过已知途径制备了反式 (1) 和顺式八氯 1,3,5-己三烯 (2)，并通过从头计算从实验和理论上研究了它们的热行为。1 和 2 中的三个双键由于八个 Cl 的空间位阻而完全解耦，如计算以及 1 的单晶 X 射线结构所示。顺式异构体 2 可以异构化为反式异构体 1通过将其加热至 220–250 °C，无论是纯净的还是溶解在高沸点溶剂中，产生大约 2:1 的反式和顺式异构体混合物。几个不同理论水平的计算预测 1 和 2 在 2 kJ mol-1 内是等能的。单分子顺式/反式异构化预计通过一种不寻常的乙烯基环丁烯中间体 7 发生，其形成面临超过 150 kJ mol-1 的障碍，但其稳定性与 1 和 2 相当。加入少量 Br2 或 Cl2 或加入 3 可大大提高异构化速率，可以用自由基诱导异构化机制来解释。三烯 1 和 2 加热到 250 °C 导致环化，产生 71% 的环戊烯异构体

表征谱图