(S)-2-(pyrrolidin-1-yl)-1-phenylethanol | 128821-02-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(pyrrolidin-1-yl)-1-phenylethanol
• 英文别名: 1-phenyl-2-(pyrrolidin-1-yl)ethanol；1-(S)-phenyl-2-(pyrrolidin-1-yl)ethanol；(1S)-1-phenyl-2-pyrrolidin-1-ylethanol
• CAS: 128821-02-3
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: FHBPYEQRIDZSBP-GFCCVEGCSA-N

物化性质

• 沸点：
  312.8±22.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-2-(pyrrolidin-1-yl)-1-phenylethanol 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.5h， 生成 (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine
  参考文献：
  名称：

  手性非外消旋二胺的高效合成：在不对称合成中的应用†

  摘要：

  已经从旋光的扁桃酸中有效地合成了各种手性二胺。衍生自一种二胺的手性非外消旋锂酰胺碱已用于天然产物如（-）-泛酮A和（-）-carbovir的形式不对称合成。©1997 Elsevier ScienceLtd。保留所有权利。

  DOI：

  10.1016/s0040-4039(97)10578-0
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 (S)-2-(pyrrolidin-1-yl)-1-phenylethanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为试剂：
  描述：

  1-苯基-2-吡咯烷-1-基乙酮 在 lithium aluminium tetrahydride 、 (S)-2-(pyrrolidin-1-yl)-1-phenylethanol 、 N-乙基苯胺 作用下， 以 乙醚 为溶剂， 生成 (S)-2-(pyrrolidin-1-yl)-1-phenylethanol 、 (R)-(-)-1-phenyl-2-(pyrrolidin-1-yl)ethanol
  参考文献：
  名称：

  Asymmetric Self-Replication of Chiral 1,2-Amino Alcohols by Highly Enantioselective Autoinductive Reduction

  摘要：

  DOI：

  10.1002/anie.199724581

文献信息

• Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
  作者：Maria Rosaria Acocella、Luciana D'Urso、Mario Maggio、Gaetano Guerra

  DOI：10.1002/cctc.201600241

  日期：2016.6.7

  The ring‐opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high‐surface‐area graphite and graphene oxide under metal‐free and solvent‐free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide

  在无金属和无溶剂条件下，高表面积的石墨和氧化石墨烯可有效地和区域选择性地催化环氧化物与胺的开环反应。对于不具有芳基的环氧化物，仅对氧化石墨烯观察到催化活性，因此，该活性必须归因于其酸性基团。相反，对于氧化苯乙烯，石墨和氧化石墨烯表现出相当相似的催化活性，因此，活性主要是由于与石墨π系统的π堆积相互作用而使亲电子环氧化物活化。所描述的氨解过程是绿色且廉价的，因为催化剂可以被回收和再循环而不损失效率。而且，
• Ruthenium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols from 1,2-Diols by “Borrowing Hydrogen”
  作者：Anggi Eka Putra、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/ejoc.201300692

  日期：2013.9

  Enantioselective synthesis of β-amino alcohols from 1,2-diols by the use of [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS catalysis was developed. Several 1,2-diols were treated with secondary amines to afford the corresponding optically active β-amino alcohols in up to 99 % yield with 77 % ee.

  开发了使用 [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS 催化从 1,2-二醇对映选择性合成 β-氨基醇。几种 1,2-二醇用仲胺处理，得到相应的光学活性 β-氨基醇，产率高达 99%，ee 为 77%。
• Boranes in synthesis. 2. Asymmetric synthesis of β-amino alcohols. A facile conversion of 2-amino acetophenones to the corresponding β-amino alcohols in high enantiomeric purity
  作者：David A. Beardsley、Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)76745-1

  日期：1994.3

  The asymmetric reduction of 2-amino acetophenones with Ipc2BH or Ipc2BCl at −78°C, yields the corresponding β-amino alcohols in good to excellent yields. Although only modest (12–45% ee) enantiomeric excesses were obtained with Ipc2BH, 75–99% enantiomeric excesses were obtained when Ipc2BCl was used as the asymmetric reducing agent.

  在-78°C下用Ipc 2 BH或Ipc 2 BCl不对称还原2-氨基苯乙酮，可生成相应的β-氨基醇，收率为好至极好。尽管使用Ipc 2 BH仅获得了适度的对映体过量（12-45％ee），但是当使用Ipc 2 BCl作为不对称还原剂时，却获得了75-99％的对映体过量。
• Pyrrolidinyl and pyrrolinyl ethylamine compounds as kappa agonists
  申请人：——

  公开号：US20010009921A1

  公开（公告）日：2001-07-26

  A compound of the following formula: 1 and the salts thereof, wherein A is hydrogen, halo, hydroxy, or the like; the broken line represents an optional double bond with proviso that if the broken line is a double bond, then A is absent; Ar 1 is optionally substituted phenyl or the like; Ar 2 is aryl or heteroaryl selected from phenyl, napththyl, pyridyl, and the like, the aryl or heteroaryl being optionally substituted; R 1 is hydrogen, hydroxy, C 1 -C 4 alkyl, or the like; and R 2 and R 3 are independently selected from optionally substituted C 1 -C 7 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyl, and the like or R 2 and R 3 , together with the nitrogen atom to which they are attached, form an optionally substituted pyrrolidine, piperidine or morpholine ring. These compounds are useful as kappa agonists.

  以下化合物的公式1及其盐，其中A为氢、卤素、羟基或类似物；断线代表可选的双键，但如果断线是双键，则A不存在；Ar1为可选的取代苯基或类似物；Ar2为苯基、萘基、吡啶基或类似的芳基或杂环芳基，该芳基或杂环芳基可选地被取代；R1为氢、羟基、C1-C4烷基或类似物；R2和R3分别选自可选的取代C1-C7烷基、C3-C6环烷基、C2-C6烯基、C2-C6炔基或类似物，或R2和R3与它们所连接的氮原子一起形成可选的取代吡咯烷、哌嗪或吗啉环。这些化合物可用作kappa受体激动剂。
• A new class of chiral modifiers for the enantioselective hydrogenation of α-ketoesters with
  作者：Keith E Simons、Guozhi Wang、Thomas Heinz、Thomas Giger、Tamas Mallat、Andreas Pfaltz、Alfons Baiker

  DOI：10.1016/0957-4166(95)00034-m

  日期：1995.2

  A series of enantiomerically pure chiral amino alcohols have been synthesized and applied as modifiers in the enantioselective hydrogenation of ethyl pyruvate over supported Pt catalysts. Their use enabled an enantiomeric excess of up to 75 %. A molecular modelling study of the modifiers and reactant on a Pt (111) surface provides a possible explanation for the observed enantiodifferentiation.