(Z)-3-bromo-1-chloropropene | 67546-49-0

• 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: (Z)-3-bromo-1-chloropropene
• 英文别名: Z-3-bromo-1-chloropropene；3-bromo-1c-chloro-propene；cis-1-chlor-3-brompropen；1-Propene, 3-bromo-1-chloro-, (1Z)-；(Z)-3-bromo-1-chloroprop-1-ene
• CAS: 67546-49-0
• 化学式: C₃H₄BrCl
• 分子量: 155.422
• InChiKey: AHUWMUAVZFJTOC-IWQZZHSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  5
• 可旋转键数：
  1
• 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

反应信息

• 作为反应物：
  描述：

  8-(1,2-二甲基庚基)-1,3,4,5-四氢-5,5-二甲基-2H-[1]苯并吡喃并[4,3-c]吡啶-10-醇 、 (Z)-3-bromo-1-chloropropene 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-(3c-chloro-allyl)-8-(1,2-dimethyl-heptyl)-5,5-dimethyl-1,3,4,5-tetrahydro-2H-chromeno[4,3-c]pyridin-10-ol
  参考文献：
  名称：

  Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles

  摘要：

  Various nitrogen analogs of delta6a,10a-tetrahydrocannabinol were synthesized by a general procedure described in an earlier communication. Minimum effective doses (MED50's) and lethal doses (LD50's) were determined by a modified Irwin mouse screen after iv administration of compounds in PEG 200. The most potent compounds were the propargyl (5t), allyl (5m), and chloroallyl (5o-q) derivatives. Overt behavioral effects (CNS depression, static ataxia, and hypersensitivity) of 5t and Roger Adams' carbocyclic analog (III) were found to be similar in the mouse, cat, dog, and monkey. Dichloroisoproterenol prevented and reversed many of the depressant effects of both III and 5t but had no effect on the ataxia produced by these compounds. In antinociceptive tests, 5t was active in the phenylquinone and Eddy hot-plate tests but was inactive in the tail-flick test.

  DOI：

  10.1021/jm00226a001
• 作为产物：
  描述：

  1-氯丙烯(顺反混合物) 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 生成 (Z)-3-bromo-1-chloropropene
  参考文献：
  名称：

  PEARSON, PAUL G.;OMISNINSKI, JAMES G.;MUERS, TIMOTNU G.;SZHUSTODERLUND, E+, CHEM. RES. TOXICOL., 3,(1990) N, C. 458-466

  摘要：

  DOI：

文献信息

• Total Synthesis of Quinolizidine Alkaloid (−)-217A. Application of Iminoacetonitrile Cycloadditions in Organic Synthesis
  作者：Kevin M. Maloney、Rick L. Danheiser

  DOI：10.1021/ol051185n

  日期：2005.7.1

  [reaction: see text] An intramolecular iminoacetonitrile [4 + 2] cycloaddition functions as the key step in an efficient total synthesis of the quinolizidine alkaloid (-)-217A.

  [反应：见正文]分子内亚氨基乙腈[4 + 2]环加成是喹唑烷生物碱（-）-217A高效全合成的关键步骤。
• Hetero-atom substituted chromium allyls: Synthetic studies on neocarzinostatin chromophore analogues
  作者：Paul A. Wender、Janet Wisniewski Grissom、Ursula Hoffmann、Robert Mah

  DOI：10.1016/s0040-4039(00)97126-0

  日期：——
• PEARSON, PAUL G.;OMISNINSKI, JAMES G.;MUERS, TIMOTNU G.;SZHUSTODERLUND, E+, CHEM. RES. TOXICOL., 3,(1990) N, C. 458-466
  作者：PEARSON, PAUL G.、OMISNINSKI, JAMES G.、MUERS, TIMOTNU G.、SZHUSTODERLUND, E+

  DOI：——

  日期：——
• Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles
  作者：Harry G. Pars、Felix E. Granchelli、Raj K. Razdan、Jacqueline K. Keller、David G. Teiger、Franklin J. Rosenberg、Louis S. Harris

  DOI：10.1021/jm00226a001

  日期：1976.4

  Various nitrogen analogs of delta6a,10a-tetrahydrocannabinol were synthesized by a general procedure described in an earlier communication. Minimum effective doses (MED50's) and lethal doses (LD50's) were determined by a modified Irwin mouse screen after iv administration of compounds in PEG 200. The most potent compounds were the propargyl (5t), allyl (5m), and chloroallyl (5o-q) derivatives. Overt behavioral effects (CNS depression, static ataxia, and hypersensitivity) of 5t and Roger Adams' carbocyclic analog (III) were found to be similar in the mouse, cat, dog, and monkey. Dichloroisoproterenol prevented and reversed many of the depressant effects of both III and 5t but had no effect on the ataxia produced by these compounds. In antinociceptive tests, 5t was active in the phenylquinone and Eddy hot-plate tests but was inactive in the tail-flick test.