(1S,2S)-1,2-Bis(chloromethyl)cyclopropane | 10523-99-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: (1S,2S)-1,2-Bis(chloromethyl)cyclopropane
• 英文别名: cis-1,2-Bis-chlormethyl-cyclopropan
• CAS: 10523-99-6；10524-00-2；89416-28-4；147527-72-8
• 化学式: C₅H₈Cl₂
• 分子量: 139.025
• InChiKey: WKZXYVDQUNSAMB-WHFBIAKZSA-N

物化性质

• 沸点：
  63-70 °C(Press: 14 Torr)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1,2-Bis(chloromethyl)cyclopropane 在 盐酸 、 氨 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 trans-1,2-bis(4-amidinophenoxymethylene)cyclopropane
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q
• 作为产物：
  描述：

  反-1,2-环丙烷二羧酸二乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 (1S,2S)-1,2-Bis(chloromethyl)cyclopropane
  参考文献：
  名称：

  Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine

  摘要：

  A series of conformationally restricted analogues of pentamidine in which the flexible central bridge has been replaced by trans-cyclopropyl, phenyl, pyridinyl, piperazinyl or homopiperazinyl groups as conformationally restricted linkers have been synthesized. The anti-Pneumocystis carinii activity of these compounds was evaluated in a cell culture model and the DNA binding affinity was determined by thermal denaturation measurements. At 1 mu M, compounds 2, 3, 5, 7, 9 and pentamidine were highly effective and caused total inhibition of P. carinii growth in culture. At 0.1 mu M, compounds 2, 5, 7 and 10 were more active than pentamidine with N, N'-bis(4-amidinophenyl)piperazine 7 being approximately 15-fold more effective than pentamidine. The most active compounds, 7 and 10, showed strong binding affinities for calf thymus DNA and poly(dA-dT); however, a clear correlation between DNA binding affinity and the in vitro anti-P. carinii activity of these compounds was not observed. The results suggest that the nature of the central Linker influences the biological actions of these compounds. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80102-0

文献信息

• Reactions of hydroxyl groups with tosylchloride-dimethylaminopyridine system. Direct synthesis of chlorides from hydroxycompounds
  作者：C.K. Hwang、W.S. Li、K.C. Nicolaou

  DOI：10.1016/s0040-4039(01)80237-9

  日期：1984.1

  The reactions of various hydroxyl groups with tosylchloride-dimethylaminopyridine system were investigated and direct syntheses of allyl, alkyl and glycosyl chlorides are described.

  研究了各种羟基与甲苯磺酰氯-二甲基氨基吡啶体系的反应，并描述了烯丙基，烷基和糖基氯化物的直接合成。