2,10-dichloro-10,11-dihydrodibenzothiepin | 4925-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 英文名称: 2,10-dichloro-10,11-dihydrodibenzothiepin
• 英文别名: 2,10-dichloro-10,11-dihydro-dibenzo[b,f]thiepin；2,10-Dichloro-10,11dihydro-dibenzo[b,f]thiepin；3,6-dichloro-5,6-dihydrobenzo[b][1]benzothiepine
• CAS: 4925-65-9
• 化学式: C₁₄H₁₀Cl₂S
• 分子量: 281.205
• InChiKey: LWUPCNLCDZFHBP-UHFFFAOYSA-N

物化性质

• 熔点：
  124.0-124.5 °C
• 沸点：
  374.2±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,10-dichloro-10,11-dihydrodibenzothiepin 在 sodium hydroxide 、 sodium ethanolate 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 ethyl N-(2-(2-chloro-10,11-dihydrodibenzothiepin-10-ylthio)ethyl)carbamate
  参考文献：
  名称：

  Valenta, Vladimir; Vlkova, Marie; Protiva, Miroslav, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 5, p. 1403 - 1421

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(2-氯-10,11-二氢二苯并[b,f]硫杂卓-10-基)-1-哌嗪乙醇 在 氯甲酸乙酯 作用下， 以 苯 为溶剂， 反应 1.0h， 以83%的产率得到2,10-dichloro-10,11-dihydrodibenzothiepin
  参考文献：
  名称：

  Valenta, Vladimir; Vlkova, Marie; Protiva, Miroslav, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 5, p. 1403 - 1421

  摘要：

  DOI：

文献信息

• 10,11-Dihydro-dibenzo(b,f)thiepin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04006144A1

  公开（公告）日：1977-02-01

  Dibenzothiepin derivatives of the general formula ##STR1## wherein m, n, R.sub.1, R.sub.2, R.sub.3 and X are as hereinafter set forth, And salts thereof as well as processes for their manufacture are disclosed. The end products are useful as central-depressant and neuroleptic agents.

  通式为##STR1##的二苯并噻吩衍生物，其中m、n、R.sub.1、R.sub.2、R.sub.3和X如下所述，以及其盐，以及其制备方法被揭示。最终产品可用作中枢抑制剂和神经阻滞剂。
• Cataleptic and noncataleptic neuroleptic agents: Synthesis and pharmacology of 4-(2-chloro and 8-chloro substituted 10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine-1-ylalkyl ethers and sulfides
  作者：Vladimír Valenta、Zdeněk Prošek、Jiřina Metyšová、Martin Valchář、Antonín Dlabač、Miroslav Protiva

  DOI：10.1135/cccc19851070

  日期：——

  The title compounds Iab-Viab were prepared by substitution reactions of 2,11-dichloro- and 2,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin with 1-(2-methoxyethyl)piperazine, 1-(3-methoxypropyl)piperazine, 1-(2-ethoxyethyl)piperazine, 1-(2-phenoxyethyl)piperazine, 1-(2-methylthioethyl)piperazine and 1-(2-phenylthioethyl)piperazine; they were transformed to hydrochlorides, maleates or methanesulfonates. Compounds of series a (8-chloro derivatives) are neuroleptics, with relatively strong cataleptic, antiapomorphine and central depressant activities (Ia, IIa, IIIa,Va) unless the volume and lipophilicity of the N-substituent exceeds certain limits (IVa and VIa are almost nontoxic and little active). Compounds of series b (2-chloro derivatives) are noncataleptic and devoid of the antiapomorphine potency; only two of them (IIb, Vb), however, showed a more pronounced effect in the test of influencing the turnover and metabolism of dopamine in the rat brain striatum.

  标题化合物是通过2,11-二氯和2,10-二氯-10,11-二氢二苯并[bf]噻吩与1-(2-甲氧基乙基)哌嗪、1-(3-甲氧基丙基)哌嗪、1-(2-乙氧基乙基)哌嗪、1-(2-苯氧基乙基)哌嗪、1-(2-甲硫氧乙基)哌嗪和1-(2-苯硫氧乙基)哌嗪的取代反应制备的；它们转化为盐酸盐、马来酸盐或甲磺酸盐。系列a的化合物(8-氯衍生物)是神经阻滞药，具有相对较强的猫状症、抗阿波莫啡和中枢抑制活性(Ia、IIa、IIIa、Va)，除非N-取代基的体积和亲脂性超过一定限制，否则IVa和VIa几乎无毒且活性较低。系列b的化合物(2-氯衍生物)不具猫状症，也没有抗阿波莫啡的作用；然而，其中只有两种(IIb、Vb)在影响大鼠脑纹状体多巴胺的转化和代谢测试中显示出更显著的效果。
• 10,11-Dihydro dibenzo(b,f)thiepin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04006145A1

  公开（公告）日：1977-02-01

  Dibenzothiepin derivatives of the general formula ##STR1## wherein m, n, R.sub.1, R.sub.2, R.sub.3 and X are as hereinafter set forth, and salts thereof as well as processes for their manufacture are disclosed. The end products are useful as central-depressant and neuroleptic agents.

  本发明揭示了通式##STR1##中m，n，R.sub.1，R.sub.2，R.sub.3和X的二苯并噻吩衍生物，以及其盐和制备过程。该终产品可用作中枢抑制剂和神经乐静剂。
• Piperazine derivatives, their acid addition salts and a process for the preparation of same
  申请人：SPOFA spojené podniky pro zdravotnickou vyrobu

  公开号：EP0321100A2

  公开（公告）日：1989-06-21

  Pharmaceutically active piperazine derivatives, particularly piperazines substituted in position 1 with a 2-­(2-chloro-10,11-dihydrodibenzo(b,f)thiepin-10-yloxy)ethyl residue and in position 4 a hydrogen atom or a methyl, 2-­hydroxyethyl, 3-hydroxypropyl, 2-(aminocarbonyl)ethyl, 2-­(acetoxy)ethyl or 2 (decanoyloxy)ethyl group, their acid addition salts and processes for the preparation thereof. The compounds are noncataleptic neuroleptics with high affinity to dopamine D-2 receptors and with in vivo antidopaminergic activity but only slight sedative, adrenolytic and anticholinergic properties; but use as antipsychotic drugs free of undesirable side effects. Said compounds are available by several routes, such as (a) reaction of 10-(2-bromo-ethoxy)-2-chloro-10,11-dihydro­dibenzo(b,f)thiepin with piperazine, 1-methylpiperazine, 2-­(1-piperazinyl)ethanol, or 3-(1 piperazinyl)propanol and (b) acylation of aminoalcohols obtained by the preceding method with chlorides of the corresponding aliphatic carboxylic acids. Preferred addition salts are succinates, maleates, hydrochlorides and methanesulphonates prepared by the respective neutralization reactions.

  具有医药活性的哌嗪衍生物，特别是在第 1 位被 2-(2-氯-10,11-二氢二苯并(b,f)硫杂卓-10-基氧基)乙基残基取代，在第 4 位被氢原子或甲基、2-羟乙基、3-羟丙基、2-(氨基羰基)乙基、2-(乙酰氧基)乙基或 2(癸酰氧基)乙基取代的哌嗪，它们的酸加成盐及其制备工艺。这些化合物属于非催眠性神经抑制剂，对多巴胺 D-2 受体具有高亲和力，在体内具有抗多巴胺能活性，但只有轻微的镇静、肾上腺素分解和抗胆碱能特性；但用作抗精神病药物没有不良副作用。上述化合物可通过以下几种途径获得：(a)10-(2-溴-乙氧基)-2-氯-10,11-二氢二苯并(b,f)硫杂卓与哌嗪、1-甲基哌嗪、2-(1-哌嗪基)乙醇或 3-(1-哌嗪基)丙醇反应；(b)通过上述方法获得的氨基醇与相应脂肪族羧酸的氯化物酰化。首选的加成盐是通过相应的中和反应制备的琥珀酸盐、马来酸盐、盐酸盐和甲磺酸盐。
• Valenta, Vladimir; Vlkova, Marie; Holubek, Jiri, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 1979 - 1994
  作者：Valenta, Vladimir、Vlkova, Marie、Holubek, Jiri、Metysova, Jirina、Protiva, Miroslav

  DOI：——

  日期：——