(E)-1,3-二氯丙-1-烯 | 6923-20-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: (E)-1,3-二氯丙-1-烯
• 英文名称: cis-1,3-dichloropropylene
• 英文别名: 1,2-Dichloropropene；2,2-dichloropropene；(Z)-1,2-dichloro-propene；1t,2-dichloro-propene；(Z)-1,2-Dichlor-propen；1t,2-Dichlor-propen；(Z)-1,2-dichloroprop-1-ene
• CAS: 6923-20-2
• 化学式: C₃H₄Cl₂
• 分子量: 110.971
• InChiKey: PPKPKFIWDXDAGC-IHWYPQMZSA-N

物化性质

• 沸点：
  88.32°C (rough estimate)
• 密度：
  1.1748 (estimate)
• 颜色/状态：
  Liquid
• 溶解度：
  In water, 2,700 mg/l @ 25 °C.
• 蒸汽密度：
  3.83 (air= 1)
• 蒸汽压力：
  90.8 mm Hg @ 20 °C
• 分解：
  When heated to decomposition it emits toxic fumes of /hydrogen chloride/.
• 保留指数：
  720

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• 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

ADMET

代谢

1,2-D在大鼠体内的代谢会导致形成一种巯基尿酸结合物，主要通过尿液排出。提出的反应中间体包括1,2-环氧丙烷；这个中间体被怀疑是1,2-D致突变效应的原因。谷胱甘肽途径被视为解毒机制，而在高浓度下可能由于这些途径的饱和导致肝脏和肾脏毒性。

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways.

来源:Hazardous Substances Data Bank (HSDB)

代谢

1,2-D在大鼠体内的代谢会导致形成一种巯基尿酸结合物，主要通过尿液排出。提出的反应中间体包括1,2-环氧丙烷；这个中间体被怀疑是1,2-D致突变效应的原因。谷胱甘肽途径被视为解毒机制，而在高浓度下可能由于这些途径的饱和导致肝脏和肾脏毒性。

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

1,2-D在大鼠体内的代谢会导致形成一种巯基尿酸结合物，主要通过尿液排出。提出的反应中间体包括1,2-环氧丙烷；这个中间体被怀疑是1,2-D致突变效应的原因。谷胱甘肽途径被视为解毒机制，而在高浓度下可能由于这些途径的饱和导致肝脏和肾脏毒性（A568）。

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways (A568).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

摄入1,2-D可能导致严重的胃肠道不适、成人呼吸窘迫综合征、血液和肝肾功能障碍、急性胃肠道不适伴有肺充血和水肿、中枢神经系统抑制，甚至在没有受损的氧气摄取情况下也可能发生。此外，这可能导致死亡。吸入后可能会迅速出现昏迷。皮肤接触后可能会出现严重的皮肤刺激和明显的表皮炎症反应，并可能影响深层组织。无论通过哪种途径，都可能对肝脏、肾脏和心脏造成晚期伤害（T48）。

Ingestion of 1,2-D can lead to developed gastrointestinal distress, adult respiratory distress syndrome, hematological and hepatorenal functional impairment, acute gastrointestinal distress with pulmonary congestion and edema, central nervous depression, perhaps even in the absence of impaired oxygen uptake. Moreover, this can lead to death. Coma may occur rapidly after inhalation. Severe skin irritation with marked inflammatory response of epidermis can underlying tissues can follow dermal exposure. By any route, possible late injuries to liver, kidneys and heart (T48).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L893）；口服（L893）；皮肤接触（L893）；眼睛接触（L893）。

Inhalation (L893) ; oral (L893) ; dermal (L893) ; eye contact (L893).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

吸入后出现的症状包括喘息、拒绝呼吸、咳嗽、胸骨下疼痛；流泪和头痛是突出的症状。吸入暴露后，不适、头痛、胸腹部不适和易怒可能会持续数周或数年。此外，眼睛和上呼吸道粘膜对浓缩蒸气的刺激反应会立即出现。摄入可能导致咳嗽、喉咙痛、头痛、头晕、恶心、呕吐、失去意识以及呼吸困难（T48，L893）。

Symptoms occuring after inhalation include gasping, refusal to breathe, coughing, substernal pain; lacrimation and headache are prominant. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability can persist during weeks or years. Moreover, Irritation of eyes and upper respiratory mucosa appears promptly after exposure to concentrated vapors. Ingestion can cause cough, sore throat, headache, dizziness, nausea, vomiting, unconsciousness, and laboured breathing (T48, L893).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2903299090

反应信息

• 作为反应物：
  描述：

  (E)-1,3-二氯丙-1-烯 在 氯 作用下， 生成 1,1,2,2-四氯丙烷
  参考文献：
  名称：

  Gerding; Haring, Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 841,847

  摘要：

  DOI：
• 作为产物：
  描述：

  (1Z)-1,2,3-trichloroprop-1-ene 在 lithium aluminium tetrahydride 作用下， 生成 (E)-1,3-二氯丙-1-烯
  参考文献：
  名称：

  Allylic Chlorides. XV. Preparation and Properties of the 1,2,3-Trichloropropenes¹

  摘要：

  DOI：

  10.1021/ja01121a029

文献信息

• ORGANIC DEUTERIUM COMPOUNDS: XI. SYNTHESIS OF 1-CHLORO-1-ALKYNES AND 1-CHLORO-1-PROPYNE-<i>d</i>₃
  作者：A. T. Morse、L. C. Leitch

  DOI：10.1139/v54-063

  日期：1954.5.1

  hydroxide in butanol has been used to prepare a number of new 1-chloro-1-alkynes, viz. 1-chloro-1-propyne-d3, 1-chloro-1-propyne, 1-chloro-1-butyne, and 1-chloro-1-pentyne in good yields. The last three compounds were also prepared by chlorination of 1-propyne, 1-butyne, and 1-pentyne with sodium hypochlorite.

  顺式1,2-二氯-1-烯烃，RCCl = CHCl，在丁醇中用氢氧化钾脱卤化氢已被用于制备许多新的1-氯-1-炔烃，即。1-氯-1-丙炔-d3、1-氯-1-丙炔、1-氯-1-丁炔和1-氯-1-戊炔收率良好。最后三种化合物也是通过用次氯酸钠氯化 1-丙炔、1-丁炔和 1-戊炔制备的。
• ORGANIC DEUTERIUM COMPOUNDS: V. THE CHLORINATION OF PROPYNE AND PROPYNE-<i>d</i>₄
  作者：L. C. Leitch

  DOI：10.1139/v53-053

  日期：1953.4.1

  Chlorination of propyne at 70 °C. gave 60 to 65% yields of 1,1,2,2-tetrachloropropane and 15 to 20% yields of trans-1,2-dichloro-1-propene. 1,1,2,2-Tetrachloropropane-d₄ was similarly prepared from propyne-d₄. Nearly theoretical yields of cis- and trans-1,2-dichloro-1-propene were obtained by partial dechlorination of tetrachloropropane. Deuterated cis- and trans-1,2-dichloro-1-propene were obtained in the same manner from 1,1,2,2-tetrachloropropane-d₄.

  在70°C下对丙炔进行氯化反应，产率为60%至65%的1,1,2,2-四氯丙烷和15%至20%的反-1,2-二氯-1-丙烯。同样地，从丙炔-d4制备了1,1,2,2-四氯丙烷-d4。通过对四氯丙烷进行部分脱氯反应，得到了接近理论产率的顺式和反式-1,2-二氯-1-丙烯。同样地，从1,1,2,2-四氯丙烷-d4中以相同方式获得了氘代的顺式和反式-1,2-二氯-1-丙烯。
• The MCPBA-oxidation of 8<i>H</i>-Cyclohepta[<i>b</i>]thiophen-8-ones to Their 1,1-Dioxides and Further Ring-contracted Benzo[<i>b</i>]thiophene Derivatives
  作者：Hitoshi Takeshita、Hideshi Motomura、Hiroaki Mametsuka

  DOI：10.1246/bcsj.57.3156

  日期：1984.11

  Upon MCPBA-oxidation, several 8H-cyclohepta[b]thiophen-8-ones yielded the 8H-cyclohepta[b]thiophen-8-one 1,1-dioxides and their epoxides. The latters were shown to be convertible to several ring-contracted derivatives, the benzo[b]thiophene 1,1-dioxides and/or their corresponding phenol and salicylaldehyde derivatives.

  MCPBA 氧化后，几个 8H-cyclohepta[b]thiophen-8-ones 产生 8H-cyclohepta[b]thiophen-8-one 1,1-dioxides 和它们的环氧化物。后者显示可转化为几种环缩衍生物，苯并 [b] 噻吩 1,1-二氧化物和/或其相应的苯酚和水杨醛衍生物。
• Free-Radical Reactions of Diazomethane with Reactive Bromopolychloroalkanes
  作者：W. H. Urry、Norman. Bilow

  DOI：10.1021/ja01063a032

  日期：1964.5.5
• Studies Directed to the Total Synthesis of ET 743 and Analogues Thereof:  An Expeditious Route to the ABFGH Subunit
  作者：Bishan Zhou、Jinsong Guo、Samuel J. Danishefsky

  DOI：10.1021/ol016844k

  日期：2002.1.1

  [GRAPHICS]In model studies directed to the total synthesis of Et743, a strategic S-C bond formation in systems 26 and 27 was demonstrated. It was further shown that Pictet-Spengler cyclization leading to spiro product 33 exhibits very high stereoselection.

表征谱图