1,1,3-trichloro-3-phenylprop-1-ene | 62098-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1,3-trichloro-3-phenylprop-1-ene
• 英文别名: 2,3,3-trichloro-2-propenylbenzene；(1, 3, 3-trichloroallyl)benzene；Benzene, (1,3,3-trichloro-2-propenyl)-；1,3,3-trichloroprop-2-enylbenzene
• CAS: 62098-05-9
• 化学式: C₉H₇Cl₃
• 分子量: 221.514
• InChiKey: GPQWWQDXHOURGX-UHFFFAOYSA-N

物化性质

• 沸点：
  279.9±35.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,3-二甲基-2-丁烯 、 1,1,3-trichloro-3-phenylprop-1-ene 在 十二烷 、 potassium tert-butylate 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以46%的产率得到(1-Chloro-2,2,3,3-tetramethyl-cyclopropylethynyl)-benzene
  参考文献：
  名称：

  摘要：

  When treated with KOH under phase-transfer catalysis or with (BuOK)-O-t, 3-substituted (alkyl or phenyl) 1, 1, 3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1, 1, 1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1, 1, 1, 3-tetrachloro-3-phenylpropane (3a) upon its treatment with (BuOK)-O-t. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1, 1, 1, 3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1, 1, 1, 3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl)-1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions; both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with (BuOK)-O-t were determined and the mechanisms for carbene generation in these reactions were proposed.

  DOI：

  10.1023/a:1020952513679
• 作为产物：
  描述：

  (1-溴-3,3,3-三氯丙基)苯 在 三乙胺 作用下， 反应 8.0h， 以28%的产率得到1,1,3-trichloro-3-phenylprop-1-ene
  参考文献：
  名称：

  摘要：

  When treated with KOH under phase-transfer catalysis or with (BuOK)-O-t, 3-substituted (alkyl or phenyl) 1, 1, 3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1, 1, 1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1, 1, 1, 3-tetrachloro-3-phenylpropane (3a) upon its treatment with (BuOK)-O-t. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1, 1, 1, 3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1, 1, 1, 3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl)-1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions; both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with (BuOK)-O-t were determined and the mechanisms for carbene generation in these reactions were proposed.

  DOI：

  10.1023/a:1020952513679

文献信息

• 1-Phenyl-3,3-dichlor-2-propenyl-(di)(thio)-phosphorsäure-ester, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
  申请人：BASF Aktiengesellschaft

  公开号：EP0008098A1

  公开（公告）日：1980-02-20

  Die vorliegende Erfindung betrifft neue 1-Phenyl-2,2-dichlor-propen-2-yl-(di)(thio)-phosphorsäureester der Formel in der R' für Methyl oder Äthyl, R2 für unverzweigtes oder verzweigtes Alkyl mit bis zu 5 Kohlenstoffatomen, X für Sauerstoff oder Schwefel, Y für Sauerstoff, Schwefel oder -N(CH3)-, Z für Halogen oder unverzweigtes oder verzweigtes Alkyl oder Alkoxy mit bis zu 4 Kohlenstoffatomen, und n für 0, 1 oder 2 stehen, die sich zur Bekämpfung von Schädlingen und lästigen Gliedertieren aus den Klassen der Insekten und Arachnoidea eignen, ein Verfahren zu ihrer Herstellung sowie Schädlingsbekämpfungsmittel, die diese Phosphorsäurederivate als Wirkstoffe enthalten.

  本发明涉及新型 1-苯基-2,2-二氯丙烯-2-基-(二)(硫)-磷酸酯，其式中 R' 为甲基或乙基，R2 为具有最多 5 个碳原子的直链或支链烷基，X 为氧或硫，Y 为氧、硫或-N(CH3)-，Z 为卤素或具有最多 4 个碳原子的直链或支链烷基或烷氧基，n 为 0、1 或 2，适用于防治害虫和恼人的昆虫和蛛形纲节肢动物，还涉及其制备方法和含有这些磷酸衍生物作为活性成分的农药。
• Martynov, A. V.; Mirskova, A. N.; Kalikhman, I. D., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 3, p. 454 - 462
  作者：Martynov, A. V.、Mirskova, A. N.、Kalikhman, I. D.、Voronkov, M. G.

  DOI：——

  日期：——
• US3998895A
  申请人：——

  公开号：US3998895A

  公开（公告）日：1976-12-21
• ——
  作者：K. N. Shavrin、V. D. Gvozdev、O. M. Nefedov

  DOI：10.1023/a:1020952513679

  日期：——

  When treated with KOH under phase-transfer catalysis or with (BuOK)-O-t, 3-substituted (alkyl or phenyl) 1, 1, 3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1, 1, 1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1, 1, 1, 3-tetrachloro-3-phenylpropane (3a) upon its treatment with (BuOK)-O-t. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1, 1, 1, 3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1, 1, 1, 3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl)-1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions; both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with (BuOK)-O-t were determined and the mechanisms for carbene generation in these reactions were proposed.