(1R,2r)-2-吡咯烷-1-环戊醇 | 32635-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2r)-2-吡咯烷-1-环戊醇
• 英文名称: trans-2-(1-Pyrrolidino)cyclopentanol
• 英文别名: trans-2-pyrrolidinocyclopentanol；(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol；2-(pyrrolidin-1-yl)cyclopentanol；trans-2-(pyrrolidin-1-yl)cyclopentanol；(1R,2R)-2-pyrrolidin-1-ylcyclopentan-1-ol
• CAS: 32635-39-5
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: YUKHVOQROHUFMM-RKDXNWHRSA-N

物化性质

• 熔点：
  34.5-35.5 °C
• 沸点：
  100-104 °C(Press: 1.2 Torr)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1R,2r)-2-吡咯烷-1-环戊醇 在 sodium hydroxide 、 sodium hydride 作用下， 反应 19.0h， 生成 (3,4-Dichloro-phenyl)-((1S,2S)-2-pyrrolidin-1-yl-cyclopentyl)-amine
  参考文献：
  名称：

  一种新型的非三环抗抑郁药。N- [反式-2-（二甲基氨基）环戊基] -N-（3,4-二氯苯基）丙酰胺及相关化合物的合成及活性。

  摘要：

  合成了一系列新的非三环抗抑郁化合物。这类化合物的代表是化合物6。研究了五个结构参数：环大小，顺/反立体化学，酰胺取代，芳族取代和胺取代。指示抗抑郁活性的药理学试验是育亨宾增强试验，氧代吗啡拮抗试验和阿扑吗啡增强试验。讨论了结构-活动关系。

  DOI：

  10.1021/jm00142a020
• 作为产物：
  描述：

  1-(1-吡咯烷)环戊烯 生成 (1R,2r)-2-吡咯烷-1-环戊醇
  参考文献：
  名称：

  Boranes in Synthesis. 5. The Hydroboration of Enamines with Mono- and Dialkylboranes. Asymmetric Synthesis of .beta.-Amino Alcohols of Moderate Enantiomeric Purity from Aldehyde Enamines

  摘要：

  The hydroboration of both acyclic and cyclic aldehyde and ketone enamines with such representative mono- and dialkylboranes as thexylborane and dicyclohexylborane, followed by an oxidative workup, yields the corresponding beta-amino alcohols in good to excellent isolated yields. The hydroboration of ketone and aldehyde enamines with the asymmetric hydroboration reagents monoisopinocampheylborane ((d)IpcBH(2)) and diisopinocampheylborane ((d)Ipc(2)BH) was also investigated, (d)Ipc(2)BH is highly effective for the asymmetric hydroboration of acyclic aldehyde enamines, such as 1-(4-morpholino)-3-phenyl-1-propene and 1-(1-pyrrolidino)-1-octene. Oxidation of the intermediate trialkylborane furnishes the corresponding beta-amino alcohols in 50-86% ee. The stereogenic center of the carbinol carbon is consistently enriched in the R-enantiomer when (d)Ipc(2)BH prepared from (+)-alpha-pinene is used as the hydroboration reagent. The enantiomeric excesses of the beta-amino alcohols synthesized in this study were determined by HPLC using a chiral stationary phase. The absolute configurations of some of the beta-amino alcohols synthesized in this study were determined by chiral HPLC comparison with authentic beta-amino alcohols prepared from chiral epoxides of known absolute configuration.

  DOI：

  10.1021/jo00112a026

文献信息

• Optimisation of the Anti-Trypanosoma brucei Activity of the Opioid Agonist U50488
  作者：Victoria C. Smith、Laura A. T. Cleghorn、Andrew Woodland、Daniel Spinks、Irene Hallyburton、Iain T. Collie、N. Yi Mok、Suzanne Norval、Ruth Brenk、Alan H. Fairlamb、Julie A. Frearson、Kevin D. Read、Ian H. Gilbert、Paul G. Wyatt

  DOI：10.1002/cmdc.201100278

  日期：2011.10.4

  Active Compounds (LOPAC) against cultured Trypanosoma brucei, the causative agent of African sleeping sickness, resulted in the identification of a number of compounds with selective antiproliferative activity over mammalian cells. These included (+)‐(1R,2R)‐U50488, a weak opioid agonist with an EC50 value of 59 nM as determined in our T. brucei in vitro assay reported previously. This paper describes

  针对培养的布氏锥虫（非洲昏睡病的病原体）筛选 Sigma-Aldrich 药理活性化合物库 (LOPAC) ，鉴定出许多对哺乳动物细胞具有选择性抗增殖活性的化合物。其中包括 (+)-(1 R ,2 R )-U50488，这是一种弱阿片类激动剂，EC 50值为 59 n M，如我们之前报道的布氏锥虫体外试验所测定。本文描述了对 U50488 关键结构元素的修饰，以研究结构-活性关系 (SAR) 并优化该化合物的抗增殖活性和药代动力学特性。
• Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1016/j.tetlet.2007.12.100

  日期：2008.2

  In the presence of a catalytic amount of Bi(OTf)3·4H2O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could

  在催化量的Bi（OTf）3 ·4H 2 O的存在下，在微波辐射下，环氧化物和胺的纯净混合物可平稳地得到相应的2-氨基醇。使多种脂族胺与环氧化烯，氧化苯乙烯和氧化二苯乙烯反应。反应进行得很快，并以高至定量的产率得到了2-氨基醇。通过简单过滤，无需水后处理即可获得所有产品。
• Facile aminolysis of epoxides with diethylaluminum amides
  作者：Larry E. Overman、Lee A. Flippin

  DOI：10.1016/0040-4039(81)80053-6

  日期：——

  Treatment of an epoxide with a diethylaluminum amide in dichloromethane at room temperature affords the corresponding β-amino alcohol in good yield.

  在室温下用二乙基铝酰胺在二氯甲烷中处理环氧化物，以良好的收率得到相应的β-氨基醇。
• Aminolysis of Epoxides Using Iridium Trichloride as an Efficient Catalyst
  作者：Rama Peddinti、Jyoti Agarwal、Anju Duley、Rashmi Rani

  DOI：10.1055/s-0029-1216899

  日期：——

  catalyzes the ring opening of epoxides by aryl, heterocyclic, or aliphatic amines under mild conditions. The reactions proceed at room temperature to afford the corresponding β-amino alcohols in excellent yields. In general, the aminolysis of cyclopentene oxide is faster than that of cyclohexene oxide in the presence of iridium trichloride as a catalyst. epoxides - iridium trichloride - amines - amino alcohols

  三氯化铱在温和的条件下通过芳基，杂环或脂肪族胺催化环氧化物的开环。反应在室温下进行，以优异的产率得到相应的β-氨基醇。通常，在三氯化铱作为催化剂的存在下，环戊烯氧化物的氨解速度比环己烯氧化物的氨解速度更快。 环氧化物-三氯化铱-胺-氨基醇-氨解
• Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 3. Enhancing activity by imposing conformational restriction in the C-4″ side chain1
  作者：Jolie A. Bastian、Nickolay Chirgadze、Michael L. Denney、Donetta S. Gifford-Moore、Daniel J. Sall、Gerald F. Smith、James H. Wikel

  DOI：10.1016/s0960-894x(98)00746-x

  日期：1999.2

  The preparation and biological evaluation of a series of benzo[b]thiophene diamine thrombin inhibitors possessing conformationally restricted C-4" linkers are reported. Compared to the parent compounds 1a/b, the unsaturated derivatives 3a/b exhibited a modest twofold increase in thrombin inhibitory activity, while the more lipophilic carbocyclic ring containing analogs 4a/b, affected an eightfold enhancement in potency. (C) 1999 Elsevier Science Ltd. All rights reserved.