(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester | 344791-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester
• 英文别名: (2S,4R)-tert-butyl-4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate；(2S,4R)-N-Boc-4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine；tert-butyl (2S,4R)-4-hydroxy-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate；tert-butyl (2S,4R)-4-hydroxy-2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carboxylate
• CAS: 344791-02-2
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: UQRLCRAFFPCNTN-MOPGFXCFSA-N

物化性质

• 沸点：
  529.7±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.0h， 生成 diphenyl((2S,4R)-4-((4-vinylbenzyl)oxy)pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  聚合物负载的手性顺式-双取代吡咯烷催化剂及其在间歇和连续流系统中的应用

  摘要：

  与从普通的反式-吡咯烷催化剂获得的那些相比，开发了聚合物负载的顺式-吡咯烷催化剂，其允许高的对映选择性和非对映选择性。不仅构型效应而且聚合效应也有助于高非对映选择性和对映选择性。聚合物催化剂也成功地应用于连续流工艺中。与间歇式系统相比，在连续流操作中观察到反应速率的加快，非对映选择性的增加和耐久性的提高。

  DOI：

  10.1021/acs.oprd.0c00268
• 作为产物：
  描述：

  L-羟基脯氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric reduction of ketones catalyzed by α,α-diphenyl-(L)-prolinol modified with imidazolium ionic liquid and BH3·SMe2 as a recoverable catalyst

  摘要：

  The synthesis of alpha,alpha-dipheny1-4-trans-hydroxy-(0-prolinol modified with imidazolium based ionic liquids was carried out with trans-alpha,alpha-dipheny1-4-hydroxy-(L)-prolinol, 5-bromovaleric acid or 1,5-dibromopentane and imidazole. alpha,alpha-Dipheny1-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquid was treated with BH3 center dot SMe2 which generate 1,3,2-oxazaborolidine, that acts as a catalyst for asymmetric reduction of prochiral ketones. a,oz-Dipheny1-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquids (PF6 anion) with BH3 center dot SMe2 found to be an efficient catalyst (10 mol%) for the reduction of the acetophenone, gave 99% yield and 87-84% ee. The catalytic method has wide applicability for a variety of substrates. 1,3,2-oxazaborolidine containing ether linkage ionic liquid was recovered and reused up to 4 cycles with 99-91% yields and 87-81% ee's. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.12.009

文献信息

• Re-visiting the diastereoselectivity of organocatalytic conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde
  作者：Liubo Li、Anton El Khoury、Brennan O. Clement、Patrick G. Harran

  DOI：10.1016/j.tetlet.2021.153056

  日期：2021.5

  We describe the re-assignment of configuration previously ascribed to product diastereomers resultant from imidazolidinone-catalyzed conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde. A modified procedure that uses a diphenylprolinol catalyst was subsequently developed to selectively provide the ‘syn’ diastereomeric product in high enantiomeric excess on decagram scales.

  我们描述了先前归因于由咪唑烷酮催化的将2-三甲基甲硅烷氧基呋喃加成反式巴豆醛的共轭加成物所产生的产物非对映异构体的构型的重新分配。随后开发了使用二苯基脯氨醇催化剂的改进方法，以十毫克级的对映体过量，选择性地提供“ syn ”非对映体产物。
• Organocatalytic Enantioselective Continuous-Flow Cyclopropanation
  作者：Patricia Llanes、Carles Rodríguez-Escrich、Sonia Sayalero、Miquel A. Pericàs

  DOI：10.1021/acs.orglett.6b03156

  日期：2016.12.16

  A set of six solid-supported diarylprolinol catalysts (varying on the anchoring strategy and the type of polymeric support) has been prepared and applied to the enantioselective cyclopropanation reaction. The selected candidate allows implementation of a long flow experiment (48 h) and generates a library of 12 cyclopropanes by sequential flow experiments. The mildness and utility of the method have

  已经制备了一组六种固体负载的二芳基脯氨醇催化剂（根据固定策略和聚合物载体的类型而异），并将其应用于对映选择性环丙烷化反应。选定的候选对象允许执行长流实验（48小时），并通过顺序流实验生成12个环丙烷的库。该方法的温和性和实用性使得能够进行伸缩过程，其中将流出物直接用于维蒂希（Wittig）流动反应中。
• The Chemzyme Membrane Reactor in the Fine Chemicals Industry
  作者：Jens Wöltinger、Andreas S. Bommarius、Karlheinz Drauz、Christian Wandrey

  DOI：10.1021/op000111i

  日期：2001.5.1

  Recovery of catalysts from homogeneous reaction mixtures is a major problem in the fine chemicals industry if the amount or the price of catalyst are not negligible. Product purification costs and ...

  如果催化剂的数量或价格不可忽略，从均相反应混合物中回收催化剂是精细化工行业的一个主要问题。产品纯化成本和...
• Immobilization of Oligostyrene-Prolinol Conjugates into Polystyrene via Electrospinning and Applications of these Fibers in Catalysis
  作者：Joachim Wendorff、Armido Studer、Caren Röben、Michael Stasiak、Birgit Janza、Andreas Greiner

  DOI：10.1055/s-2008-1067146

  日期：2008.7

  This paper reports the synthesis of prolinol-oligostytrene conjugates and their immobilization into a polystyrene matrix by using the electrospinning process. Via this approach fibers with a large surface area (fiber diameter of 1.2 µm) containing the prolinol conjugate are readily obtained. The fibers are shown to be catalytically active in a test Michael reaction. The fibrous catalyst system can readily be removed from the reaction mixture and be reused. However, a decrease of the catalyst activity was noticed upon recycling the fibrous catalyst systems.

  本文报道了以电纺法合成的脯氨醇-低聚苯乙烯共轭物，并将其固定于聚苯乙烯基质中的研究。通过这种方法可以轻松地获得具有较大表面积（纤维直径为1.2微米）且含有脯氨醇共轭物的纤维。这些纤维在迈克尔反应测试中表现出催化活性。该纤维催化剂系统可以轻松地从反应混合物中去除并重复使用。然而，在循环使用纤维催化剂系统时注意到催化活性的下降。
• Recyclable and reusable chiral α, α-L-diaryl prolinol heterogeneous catalyst grafting to UiO-67 for enantioselective hydration/aldol/oxa-Diels Alder domino reaction
  作者：Hao Ren、Lin Cheng、Jinghua Yang、Kaiyuan Zhao、Qingchao Zhai、Yiming Li

  DOI：10.1016/j.catcom.2020.106249

  日期：2021.1

  α-L-Diaryl prolinol was first introduced into a highly stable porous MOF, UiO-67, via the immobilization of a chiral prolinol side chain into 4,4′-biphenyldicarboxylic acid through a five-step process, to construct a chiral heterogeneous catalyst. The catalyst exhibited high yield (up to 88%) and excellent stereoselectivities (up to >4:1 dr, > 80% ee) for the enantioselective hydration/aldol/oxa-Diels

  α，α-L-二芳基脯氨醇首次引入到一个高度稳定的多孔MOF，UIO-67，通过手性脯氨醇侧链的固定化到4,4'-联苯二羧酸通过五个步骤，以构建手性多相催化剂。该催化剂表现出高收率（高达88％）和出色的立体选择性（高达> 4：1 dr，> 80％ee），用于对映选择性水合/羟醛/氧杂-Diels Alder多米诺骨牌反应，并具有良好的可重复使用性和可循环利用性进行三次，而不会明显丧失活动能力。据我们所知，这是手性MOF作为不​​对称多米诺骨牌反应的多相催化剂的首次报道。