cis-1,2-diaminocyclopropane | 45347-36-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis-1,2-diaminocyclopropane
• 英文别名: cis-Cyclopropane-1,2-diamine；(1S,2R)-cyclopropane-1,2-diamine
• CAS: 45347-36-2
• 化学式: C₃H₈N₂
• 分子量: 72.1099
• InChiKey: DQSBSLFFVASXRY-WSOKHJQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1,2-diaminocyclopropane 、 苯甲醛 在 sodium acetate 作用下， 以 四氯乙烯 为溶剂， 反应 3.0h， 以64%的产率得到cis-2,3-Dihydro-2,3-diphenyl-1H-1,4-diazepin
  参考文献：
  名称：

  Quast, Helmut; Seidenspinner, Hubert-Matthias; Stawitz, Josef, Liebigs Annalen der Chemie, 1983, # 7, p. 1207 - 1229

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-1,2-cyclopropanediammonium dibromide 在 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 生成 cis-1,2-diaminocyclopropane
  参考文献：
  名称：

  2,3-Homo-6H-1,4-diazepinium Dications 的 2,2'-Bis-azonia-Cope 重排

  摘要：

  顺式-1,2-环丙二胺与 1,3-二羰基化合物和 1,5-二氮杂戊二烯盐的缩合得到 2,3-homo-1H-1,4-二氮杂鎓盐，其被非常强的酸质子化得到 2 ,3-homo-6H-1,4-diazepinium 药物。作为碱度的量度，对于 2,3-均-和 2,3-二氢-1H-1,4-二氮杂鎓盐，测定半质子化时水在三氟甲磺酸中的摩尔分数。2,3-Homo-6H-1,4-diazepinium dications 经历了 2,2'-bis-azonia-Cope 重排，这可以从产物结构或涉及环丙烷环亚甲基的 H/D 交换推断出来。显然，在 Cope 重排中，该基团与七元环 (C-6) 中的亚甲基互换，后者在强氘酸中容易发生 H/D 交换。快速、退化、以及以这种方式发现了非常缓慢、强烈偏向的 Cope 重排。在升高的温度下记录母体二阳离子在三氟甲磺酸中的溶液的 1H NMR 光谱揭示了交换 2-H、3-H

  DOI：

  10.1002/ejoc.201300386

文献信息

• Pyrroles from 1,2-Cyclopropanediamines and Aldehydes
  作者：Wolfgang von der Saal、Robert Reinhardt、Josef Stawitz、Helmut Quast

  DOI：10.1002/(sici)1099-0690(199808)1998:8<1645::aid-ejoc1645>3.0.co;2-h

  日期：1998.8

  proton spectroscopy detected intermediates and uncovered the course of reactions in acetate-buffered [D4]methanol of primary cyclopropanediamines cis- and trans-2a with benzaldehyde (3a) or 2,2-dimethylpropanal (3b), of secondary cyclopropanediamines cis- and trans-2b with 3b, and of the ring-methylated cyclopropanediamine trans-14a and the aromatic aldehydes 3a and c. This study provided the basis

  通过质子光谱的机理研究检测到中间体，并揭示了一级环丙二胺顺式和反式 2a 在乙酸盐缓冲的 [D4] 甲醇中与苯甲醛 (3a) 或 2,2-二甲基丙醛 (3b) 二级环丙二胺的反应过程顺式和反式 2b 与 3b，以及环甲基化环丙二胺 trans-14a 和芳香醛 3a 和 c。该研究为在异常温和的条件下方便地合成吡咯奠定了基础。无论构型如何，没有环取代基的伯 (2a·2HBr) 和仲环丙二溴化二铵 2b 和 c·2HBr 与芳香醛 3a、e-h、肉桂醛 (3i) 和 3b 反应得到 2-取代的 ( 8a, b) 和 1,2-二取代的吡咯 (8c-i)，分别。
• 7-(substituted)cycloalkylamino-1
  申请人：American Cyanamid Company

  公开号：US04992449A1

  公开（公告）日：1991-02-12

  Novel antibacterial compounds of the formula: ##STR1## in which R.sub.1 is alkyl (C.sub.1 -C.sub.4), cycloalkyl (C.sub.3 -C.sub.6), alkoxy (C.sub.1 -C.sub.4), alkylamino (C.sub.1 -C.sub.3), vinyl, phenyl, benzyl, --CH.sub.2 CH.sub.2 F or mono or polysubstituted phenyl (wherein the substituent is halogen, CF.sub.3 or OCH.sub.2 F); n is an integer of from 1 to 4; and R.sub.2 is cis or trans hydroxy, amino, mono or disubstituted alkyl (C.sub.1 -C.sub.3) amino and the pharmacologically accepted salts thereof are described.

  本发明提供了一种新的抗菌化合物，其化学式为： ##STR1## 其中R.sub.1是烷基（C.sub.1-C.sub.4），环烷基（C.sub.3-C.sub.6），烷氧基（C.sub.1-C.sub.4），烷基胺（C.sub.1-C.sub.3），乙烯基，苯基，苄基，--CH.sub.2 CH.sub.2 F或单或多取代苯基（其中取代基为卤素，CF.sub.3或OCH.sub.2 F）; n是1至4的整数; R.sub.2是顺式或反式羟基，氨基，单或双取代烷基（C.sub.1-C.sub.3）氨基及其药学上可接受的盐。
• FGF-RECEPTOR AGONIST DIMERIC COMPOUNDS
  申请人：BONO Francoise

  公开号：US20090069368A1

  公开（公告）日：2009-03-12

  FGF receptor agonist compounds corresponding to the general formula: M1-L-M2 are disclosed in which M1 and M2, which may be identical or different, each represent, independently of one another, a monomer unit M, and L represents a linker group, wherein the monomer unit is of the general formula I.

  本发明揭示了一种对应于一般式M1-L-M2的FGF受体激动剂化合物，其中M1和M2可以相同也可以不同，每个代表单体单元M，L代表连接基团，其中单体单元的一般式为I。
• FGF-receptor agonist dimeric compounds
  申请人：Bono Francoise

  公开号：US09120819B2

  公开（公告）日：2015-09-01

  FGF receptor agonist compounds corresponding to the general formula: M1-L-M2 are disclosed in which M1 and M2, which may be identical or different, each represent, independently of one another, a monomer unit M, and L represents a linker group, wherein the monomer unit is of the general formula I.

  本发明公开了与一般式M1-L-M2相对应的FGF受体激动剂化合物，其中M1和M2（可以相同也可以不同）各自独立地表示单体单元M，L表示连接基团，其中单体单元具有一般式I。
• Conformationally Restricted Analogues of ¹<i>N</i>,¹²<i>N</i>-Bisethylspermine:  Synthesis and Growth Inhibitory Effects on Human Tumor Cell Lines
  作者：Venodhar K. Reddy、Aldonia Valasinas、Aparajita Sarkar、Hirak S. Basu、Laurence J. Marton、Benjamin Frydman

  DOI：10.1021/jm980172v

  日期：1998.11.1

  Eight analogues of N-1,N-12-bisethylspermine (BES) with restricted conformations were synthesized in the search for new spermine mimetics with cytotoxic activities. By replacing the central butane segment of BES with a 1,2-disubstituted cyclopropane ring, a pair of cis/trans-isomers was obtained that introduced a spatial constraint in the otherwise freely mobile butane chain. An analogous pair of isomers was obtained when the butane segment was replaced with a 1,2-disubstituted cyclobutane ring or with a 2-butene residue. The six new BES analogues thus obtained.(three pairs of cis/trans-isomers) were growth inhibitory at low-micromolar concentrations against four human tumor cell lines (A549, HT-29, U251MG, and DU145) but were less growth inhibitory against two other human tumor cell lines (PC-3 and MCF7). N-1,N-12-Bisethylspermyne, where the central butane segment of BES was replaced by the rigid 2-butyne segment, was devoid of growth inhibitory activity against five of the six human cell lines studied (DU145 being the only exception), a clear indication of the importance of conformational mobility at the N-4,N-9-butane segment of BES for its biological activity. When the butane segment was replaced by a benzene-1,2-dimethyl residue, the resulting BES analogue was devoid of growth inhibitory activity despite its cisoid conformation. The cytotoxicity of the analogues does not seem to be directly related to their uptake by the cells or to their effects on cellular polyamine levels. BES analogues with restricted conformations but which contained the equivalent of a two-carbon unit, rather than the natural four-carbon unit, at the central segment, such as 1,2-diaminocyclopropyl or 1,2-diaminocyclobutyl derivatives, were devoid of growth inhibitory effects at the concentrations studied. The development of conformationally restricted polyamine analogues appears to show promise in the further quest for polyamine-related therapeutic agents with specificity of action.