3-chloro-1--2-propane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 3-chloro-1--2-propane
• 英文别名: 2-[bis(trifluoromethyl)amino]oxy-3-chloro-N,N-bis(trifluoromethyl)propan-1-amine
• 化学式: C₇H₅ClF₁₂N₂O
• 分子量: 396.563
• InChiKey: VCXXASKSVVJVTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane) 、 3-氯丙烯 反应 48.0h， 以82%的产率得到3-chloro-1--2-propane
  参考文献：
  名称：

  Reaction of perfluoro-(2,4-dimethyl-3-oxa-2,4-diazapentane) with propene, but-2-ene and halogeno derivatives

  摘要：

  Reaction of the oxadiazapentane (CF3)2NON(CF3)2 (1) with an excess of the propenes CH2 = CXR (X = H or Cl, R = Me or CH2Cl) at room temperature gives high yields (92%-97%) of mixtures of the 1:1 adducts (CF3)2NCH2CXRON(CF3)2 (3) and (CF3)2NCXRCH2ON(CF3)2 (4) in the ratio 87:13 to 90:10 via initial (CF3)2N. radical attack. In contrast, the corresponding reactions of the alkenes CH2 = CClR (R = Me, CH2Cl) with the N-bromoamine (CF3)2NBr (2) under free-radical conditions results in monodirectional (CF3)2N. radical attack to give the 1:1 adducts (CF3)2NCH2CBrClR (14) (95%-98%). With the alkenes CH2 = CHCF3 and CCl2 = CHMe, reaction with 1 affords the adducts (CF3)2NCH2CH(CF3)ON(CF3)2 (3e) (96%) and (CF3)2NCHMeCCl2ON(CF3)2 (10) (86%), respectively, but 3-bromopropene gives a complex mixture of products including the alkene (CF3)2NCH2CH = CH2 (7) (4%), the compound [(CF3)2NCH212CHON(CF3)2 (8) (24%) and the dibromide (BrCH2)2CHON(CF3)2 (9) (48%). Treatment of (E)- or (Z)-but-2-ene with 1 gives in each case a mixture (c. 80%) of the erythro and threo 1:1 adducts (CF3)2NCHMeCHMeON(CF3)2 (11) in the ratio 75:25, while from (E)-1-chlorobut-2-ene the adducts (CF3)2NCH(CH2Cl)CHMeON(CF3)2 (12) (54%) and (CF3)2NCHMeCH(CH2Cl)ON(CF3)2 (13) (42%) are formed each as a mixture of the erythro and threo isomers.

  DOI：

  10.1016/0022-1139(93)02983-l

文献信息

• Reaction of perfluoro-(2,4-dimethyl-3-oxa-2,4-diazapentane) with propene, but-2-ene and halogeno derivatives
  作者：Gordon Newsholme、Anthony E. Tipping

  DOI：10.1016/0022-1139(93)02983-l

  日期：1994.7

  Reaction of the oxadiazapentane (CF3)2NON(CF3)2 (1) with an excess of the propenes CH2 = CXR (X = H or Cl, R = Me or CH2Cl) at room temperature gives high yields (92%-97%) of mixtures of the 1:1 adducts (CF3)2NCH2CXRON(CF3)2 (3) and (CF3)2NCXRCH2ON(CF3)2 (4) in the ratio 87:13 to 90:10 via initial (CF3)2N. radical attack. In contrast, the corresponding reactions of the alkenes CH2 = CClR (R = Me, CH2Cl) with the N-bromoamine (CF3)2NBr (2) under free-radical conditions results in monodirectional (CF3)2N. radical attack to give the 1:1 adducts (CF3)2NCH2CBrClR (14) (95%-98%). With the alkenes CH2 = CHCF3 and CCl2 = CHMe, reaction with 1 affords the adducts (CF3)2NCH2CH(CF3)ON(CF3)2 (3e) (96%) and (CF3)2NCHMeCCl2ON(CF3)2 (10) (86%), respectively, but 3-bromopropene gives a complex mixture of products including the alkene (CF3)2NCH2CH = CH2 (7) (4%), the compound [(CF3)2NCH212CHON(CF3)2 (8) (24%) and the dibromide (BrCH2)2CHON(CF3)2 (9) (48%). Treatment of (E)- or (Z)-but-2-ene with 1 gives in each case a mixture (c. 80%) of the erythro and threo 1:1 adducts (CF3)2NCHMeCHMeON(CF3)2 (11) in the ratio 75:25, while from (E)-1-chlorobut-2-ene the adducts (CF3)2NCH(CH2Cl)CHMeON(CF3)2 (12) (54%) and (CF3)2NCHMeCH(CH2Cl)ON(CF3)2 (13) (42%) are formed each as a mixture of the erythro and threo isomers.