(Z)-2,3-methano-5-bromopentan-1-ol | 129920-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-2,3-methano-5-bromopentan-1-ol
• 英文别名: [(1S,2S)-2-(2-bromoethyl)cyclopropyl]methanol
• CAS: 129920-67-8
• 化学式: C₆H₁₁BrO
• 分子量: 179.057
• InChiKey: YWIUPHUHDBXHME-PHDIDXHHSA-N

物化性质

• 沸点：
  223.8±13.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-methano-5-bromopentan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (Z)-2,3-methano-5-(diethylphosphono)pentanal
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid

  摘要：

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).

  DOI：

  10.1021/jm00105a024
• 作为产物：
  描述：

  (Z)-ethyl 2,3-methano-5-bromopentanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.67h， 以75%的产率得到(Z)-2,3-methano-5-bromopentan-1-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid

  摘要：

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).

  DOI：

  10.1021/jm00105a024

文献信息

• Highly Enantioselective Oxidation of <i>cis</i>-Cyclopropylmethanols to Corresponding Aldehydes Catalyzed by Chloroperoxidase
  作者：Shanghui Hu、Jonathan S. Dordick

  DOI：10.1021/jo016161i

  日期：2002.1.1

  catalyzes the enantioselective oxidation of cyclopropylmethanols. This finding enables a novel route to the synthesis of optically active cyclopropane derivatives, which occur widely in natural products and compounds of pharmaceutical interest. In addition, chiral cyclopropane molecules may be useful model substrates to investigate reaction mechanisms of CPO and the related cytochromes P450.

  氯过氧化物酶（CPO）使用叔丁基氢过氧化物作为末端氧化剂，催化环丙基甲醇（例如2-甲基环丙基甲醇）的对映选择性氧化为环丙基醛。在所有情况下，尽管CPO对两种异构体都具有相似的催化活性，但顺式环丙烷的CPO氧化显示出比反式异构体高得多的对映选择性。这是血红素酶催化环丙基甲醇对映选择性氧化的第一个例子。该发现为光学活性环丙烷衍生物的合成提供了一条新途径，该化合物广泛存在于天然产物和具有药物意义的化合物中。此外，手性环丙烷分子可能是研究CPO与相关细胞色素P450反应机理的有用模型底物。