O-Hex-2-ynyl-hydroxylamine; hydrochloride | 137270-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-Hex-2-ynyl-hydroxylamine; hydrochloride
• 英文别名: Hydroxylamine, O-2-hexynyl-, hydrochloride；O-hex-2-ynylhydroxylamine;hydrochloride
• CAS: 137270-30-5
• 化学式: C₆H₁₁NO*ClH
• 分子量: 149.62
• InChiKey: SDSPEUIFZXMOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-Hex-2-ynyl-hydroxylamine; hydrochloride 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 7.5h， 以60%的产率得到3-propyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  O-炔丙基羟胺通过串联重排-环化反应制备2-异恶唑啉

  摘要：

  描述了一种以 60-84% 的产率将 O-炔丙基羟胺转化为 2-异恶唑啉的方法。对于3-烷基炔丙基或3-芳基炔丙基羟胺，这是通过在K 2 CO 3 存在下加热盐酸盐的甲醇溶液来实现的。在 3-未取代化合物的情况下，盐酸盐首先转化为游离碱，在甲醇中加热后重新排列。在一个案例中，通过在室温下用甲基肼处理超过 19 小时，该方法被扩展为能够以 65% 的产率将邻炔丙基邻苯二甲酰亚胺直接转化为 2-异恶唑啉。

  DOI：

  10.1055/s-2006-926232

文献信息

• Synthesis and in vitro muscarinic activities of a Series of 1,3-diazacycloalkyl carboxaldehyde oxime derivatives
  作者：Ralf Plate、Christan G.J.M Jans、Marc J.M Plaum、Thijs de Boer

  DOI：10.1016/s0968-0896(01)00379-0

  日期：2002.4

  tested for muscarinic activity in receptor binding assays using [3H]-oxotremorine-M (OXO-M) and [3H]-pirenzepine (PZ) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies measuring their potencies to inhibit the binding of OXO-M and PZ. Preferential inhibition of OXO-M binding was used as an indicator for potential muscarinic agonistic

  合成了一系列的1,3-二氮杂环烷基羧醛肟衍生物，并以[3H]-氧代脱氢吗啡-M（OXO-M）和[3H]-哌仑西平（PZ）作为配体，在受体结合测定中测试了毒蕈碱活性。使用结合研究确定化合物的潜在毒蕈碱激动或拮抗特性，该研究测量了其抑制OXO-M和PZ结合的能力。OXO-M结合的优先抑制被用作潜在的毒蕈碱激动特性的指标；在隔离器官的功能研究中证实了这种潜力。
• Synthesis, and In vitro and In vivo muscarinic pharmacological properties of a series of 1,6-Dihydro-5-(4 H )-pyrimidinone oximes
  作者：Ralf Plate、Marc J.M. Plaum、Peter Pintar、Christan G. Jans、Thijs de Boer、Fred A. Dijcks、Ge Ruigt、John S. Andrews

  DOI：10.1016/s0968-0896(98)00074-1

  日期：1998.9

  A series of 1,6-dihydro-5-(4H)-pyrimidinone oxime derivatives I was synthesized (Scheme 1, Tables 1 and 2) and tested for muscarinic activity (Table 3) in receptor binding assays using [H-3]-oxotremorine-M (Oxo-M) and [H-3]-pirenzepine pirenzepine (Pz) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies that measured their potencies to inhibit the binding of Oxo-M and Pz. Preferential inhibition of Oxo-M binding was used as an indicator for potential muscarinic agonistic properties; this potential was confirmed in functional studies on isolated organs. The series produced a wide range of active compounds with differing degrees of selectivity in M-1, M-2, and M-3 functional models. Several compounds that have mixed agonist/antagonist profiles were able to reduce cholinergic-related cognitive impairments in models of mnemonic function. Substitutions (I, e.g. R-2 or R-3 = Me) at the 1,6-dihydro-5-(4H)pyrimidine ring disrupted binding and efficacy, whereas systematic variation of the oximes substituent R1 resulted in various degrees of potency and selectivity dependent on the nature of the substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.