(1R,2R)/(1S,2S)-2-(4-morpholinyl)cyclopentan-1-ol | 109433-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,2R)/(1S,2S)-2-(4-morpholinyl)cyclopentan-1-ol
• 英文别名: trans-2-(morpholin-4-yl)cyclopentanol；trans-2-(4-Morpholino)cyclopentanol；trans-2-morpholinocyclopentanol；2-morpholinocyclopentanol；1-(Morpholin-4-yl)-2-hydroxy-cyclopentane；(1R,2R)-2-morpholin-4-ylcyclopentan-1-ol
• CAS: 109433-72-9
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: BDLQQULXCVFFIX-RKDXNWHRSA-N

物化性质

• 沸点：
  110-114 °C(Press: 0.6 Torr)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 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：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)/(1S,2S)-2-(4-morpholinyl)cyclopentan-1-ol 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (1R,2R)/(1S,2S)-1-(2-naphthalenethoxy)-2-(4-morpholinyl)cyclopentane
  参考文献：
  名称：

  新型2-氨基烷基醚作为潜在的抗心律不齐药物用于房颤转化的合成和生物学研究。

  摘要：

  描述了制备为潜在抗心律不齐药的一系列2-氨基烷基醚。本发明的化合物是混合的钠和钾离子通道阻滞剂，并且在缺血引起的心律不齐的大鼠模型中表现出抗心律不齐的活性。结构活性研究导致鉴定了三种化合物5、18和26，这是根据它们的特定体内电生理特性选择的，用于两种犬心房颤动（AF）模型的研究。在这两种模型中，这三种化合物均可转化为AF，但仅化合物26被证明具有口服生物利用度。将外消旋物26拆分为其相应的对映体40和41，然后对这些对映体进行生物学测试，结果导致选择（1S，

  DOI：

  10.1021/jm0604528
• 作为产物：
  描述：

  dimethyl trans-(2-morpholinocyclopentyl)boronate 生成 (1R,2R)/(1S,2S)-2-(4-morpholinyl)cyclopentan-1-ol
  参考文献：
  名称：

  Hydroboration. 81. Synthesis of 2-(dialkylamino)boronic esters and acids via hydroboration of enamines. A convenient preparation of .beta.-dialkylamino alcohols

  摘要：

  DOI：

  10.1021/jo00227a014

文献信息

• 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。
• 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
• 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
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Dennis L. Hasha、Donald Zakett、Bakthan Singaram

  DOI：10.1021/jo00112a026

  日期：1995.4

  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.
• GORALSKI, CH. T.;SINGARAM, B.;BROWN, H. C., J. ORG. CHEM., 52,(1987) N 18, 4014-4019
  作者：GORALSKI, CH. T.、SINGARAM, B.、BROWN, H. C.

  DOI：——

  日期：——