1-氯-2-羟基-3-(1-哌啶基)-丙烷 | 15285-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-氯-2-羟基-3-(1-哌啶基)-丙烷
• 中文别名: 1-哌啶乙醇,a-(氯甲基)-
• 英文名称: (+/-)-1-chloro-3-(piperidino-1)-2-propanol
• 英文别名: 1-chloro-3-piperidin-1-ylpropan-2-ol；(RS)-1-chloro-3-(piperidin-1-yl)propan-2-ol；N-(3-Chlor-2-hydroxypropyl)-piperidin；1-chloro-2-hydroxy-3-(1-piperidinyl)-propane；3-piperidino-2-hydroxy-1-chloro-propane；1-chloro-3-(1-piperidinyl)-2-propanol；1-Chlor-3-piperidino-propan-2-ol
• CAS: 15285-63-9
• 化学式: C₈H₁₆ClNO
• 分子量: 177.674
• InChiKey: IGMZDGBNMCELOE-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  278.6±25.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氯-2-羟基-3-(1-哌啶基)-丙烷 在 吡啶 、 Pseudomonas aeruginosa MTCC 5113 lipase 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (R)-1-chloro-3-(piperidin-1-yl)propan-2-yl acetate
  参考文献：
  名称：

  New chemo-enzymatic synthesis of (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol

  摘要：

  The present study deals with the efficient chemo-enzymatic synthesis of enantiopure (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol 3, as an intermediate for (R)-arimoclomol. This intermediate was synthesized from racemic alcohol (RS)-3 using lipases with vinylacetate as the acyl donor in three different ionic liquids (1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4], 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6],and 1-ethyl-3-methyl imidazolium tetrafluoroborate [EMIM][BF4]) in combination with an organic solvent (toluene). Various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium (organic solvent and ionic liquid) were optimized using Pseudomonas aeruginosa MTCC 5113 lipases (PAL). It was observed that 30 mM of (RS)-3 and 30 mg/mL of PAL in 4 mL of solvent (toluene:[BMIM][BF4]::70:30) using vinyl acetate as the acyl donor at 30 degrees C gave good conversion (C = 50.02%) and enantiomeric excess (ee(P) = 98.91% and ee(S) = 99%) in 18 h. The (S)-1-chloro-3-(piperidin-1-yl) propan-2-yl acetate 4 and (R)-3 were separated by flash chromatography. Compound (R)-3 is a key intermediate for the synthesis of enantiopure arimoclomol and bimoclomol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.008
• 作为产物：
  描述：

  哌啶 、 环氧氯丙烷 在 bismuth (III) nitrate pentahydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.02h， 以80%的产率得到1-氯-2-羟基-3-(1-哌啶基)-丙烷
  参考文献：
  名称：

  使用Bi（NO 3）3 ·5H 2 O作为催化剂的微波辐射下胺在环氧化物上的区域选择性开环的有效方法†

  摘要：

  硝酸铋（III）五水合物，一种高效的环境友好型催化剂，用于在无溶剂微波条件下与芳香族，脂肪族和杂芳香族胺一起对环氧氯丙烷和氧化苯乙烯进行亲核开环，从而大大缩短了反应时间，从而提供了相应的β-氨基醇具有良好的收率和优异的选择性，并具有较高的区域选择性。获得的产物通过柱色谱法直接纯化，并通过1 H和13 C NMR，FTIR和质谱进行表征。

  DOI：

  10.1039/c6nj03701a

文献信息

• Synthesis and pharmacological evaluation of 5-dialkylaminomethyl-2-amino-2-oxazolines as H1-antagonists
  作者：J J Bosc、C Jarry、B Martinez、M Molimard

  DOI：10.1211/0022357011776315

  日期：2010.2.18

  New 5-dialkylaminomethyl-2-amino-2-oxazolines have been synthezised in two steps from the corresponding dialkylamines. They were evaluated in-vitro as H1-antagonists. Compounds 1c, 1d and 1j significantly antagonized histamine-induced contraction of guinea-pig trachea with a rightward shift of the concentration-response curve to histamine. Compound 1f, 5-[(4-benzyl-1-piperidinyl)methyl]-2-amino-2-oxazoline, induced an increase in acetylcholine Emax (the maximal response to acetylcholine 10−3 M) and a shift to the left of the concentration-response curve. The lack of effect of this compound on histamine-induced contraction rules out a non-selective potentiation of the contraction mechanisms. Preliminary structure-activity results were reported partly based on physicochemical results.

  摘要：从相应的二烷基胺中，通过两步合成了新的5-二烷基氨甲基-2-氨基-2-噁唑啉。它们在体外被评估为H1-拮抗剂。化合物1c、1d和1j显著拮抗了组织胺诱导的豚鼠气管收缩，使组织胺的浓度-反应曲线向右移。化合物1f，5-[(4-苄基-1-哌啶基)甲基]-2-氨基-2-噁唑啉，导致乙酰胆碱Emax（对乙酰胆碱10^-3 M的最大反应）增加，并使浓度-反应曲线向左移。该化合物对组织胺诱导的收缩无影响，排除了非选择性增强收缩机制的可能性。初步的结构活性结果部分基于理化结果报告。
• Hydroxylamine derivatives useful for enhancing the molecular chaperon production and the preparation thereof
  申请人：Biorex Research & Development Co.

  公开号：US06653326B1

  公开（公告）日：2003-11-25

  A method of increasing expression of a molecular chaperon by a cell and/or enhancing the activity of a molecular chaperon in cells is provided. The method comprises treating a cell that is exposed to a physiological stress which induces expression of a molecular chaperon by the cell with an effective amount of a certain hydroxylamine derivative to increase the stress. Alternatively; an hydroxylamine derivative can be administrated to a cell before it is exposed to a physiological stress which induces expression of a molecular chaperon by the cell. Preferably, the cell to which an hydroxylamine derivative is administered is an eukaryotic cell. The hydroxylamine derivative corresponds to the formulae (I) or (II). The invention also provides novel hydroxyl amine derivatives falling within the scope of the formulae (I) and (II) as well as pharmaceutical and/or cosmetical compositions comprising the said compounds.

  提供了一种通过细胞增加分子伴侣的表达和/或增强细胞中分子伴侣活性的方法。该方法包括将暴露于诱导细胞表达分子伴侣的生理应激的细胞用有效量的某种羟胺衍生物进行处理，以增加应激。或者；可以在细胞暴露于诱导细胞表达分子伴侣的生理应激之前向细胞施加羟胺衍生物。最好，施加羟胺衍生物的细胞是真核细胞。羟胺衍生物对应于式（I）或（II）。本发明还提供了新颖的羟胺衍生物，属于式（I）和（II）范围内，以及包含所述化合物的药用和/或化妆品组合物。
• 0-(3-amino-2-hydroxypropyl)-hydroximic acid halides and process for
  申请人：Biorex Kutato-Fejleszto KFT

  公开号：US05328906A1

  公开（公告）日：1994-07-12

  Hydroximic acid derivatives of the formula ##STR1## These compounds are useful for treating diabetes angiopathy.

  公式为##STR1##的羟肟酸衍生物，可用于治疗糖尿病血管病变。
• New O-(3-amino-2-hydroxy-propyl)-amidoxime derivatives, process for the
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.

  公开号：US04187220A1

  公开（公告）日：1980-02-05

  A compound effective in the treatment of diabetic angiopathy, i.e. a selective .beta.-receptor blocker has the formula ##STR1## wherein: R.sup.2 is a hydrogen or alkyl having one to five carbon atoms, R.sup.3 is alkyl having one to five carbon atoms, cycloalkyl or phenyl optionally substituted with hydroxyl or phenyl, or R.sup.2 and R.sup.3 together form a five- to eight-membered ring optionally containing also other heteroatoms and/or fused with an other ring, preferably phenyl, naphthyl, quinolyl, isoquinolyl, pyridyl, pyrazolyl, R.sup.5 is hydrogen or alkyl having one to four carbon atoms, cycloalkyl or phenyl optionally substituted with halogen, alkoxy having one to four carbon atoms or alkyl having one to four carbon atoms, R.sup.6 is hydrogen, alkyl having one to four carbon atoms or phenyl, m=0, 1 or 2, and n=0, 1 or 2.

  一种用于治疗糖尿病血管病的复合物，即一种选择性β受体阻滞剂，其化学式为##STR1##其中：R.sup.2是氢或具有一到五个碳原子的烷基，R.sup.3是具有一到五个碳原子的烷基，环烷基或苯基，可选择性地用羟基或苯基取代，或者R.sup.2和R.sup.3共同形成一个五到八元环，也可以含有其他杂原子和/或与其他环融合，优选苯基，萘基，喹啉基，异喹啉基，吡啶基，吡唑基，R.sup.5是氢或具有一到四个碳原子的烷基，环烷基或苯基，可选择性地用卤素，具有一到四个碳原子的烷氧基或烷基取代，R.sup.6是氢，具有一到四个碳原子的烷基或苯基，m=0，1或2，n=0，1或2。
• O-(3-amino-2-hydroxypropyl)-hydroximic acid halides and process for
  申请人：Biorex Kutato-Fejleszto Kft

  公开号：US05147879A1

  公开（公告）日：1992-09-15

  Hydroximic acid derivatives of the formula ##STR1## These compounds are useful for treating diabetes angiopathy.

  式为##STR1##的羟肟酸衍生物。这些化合物对治疗糖尿病血管病变有用。