trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride | 1173184-14-9

• 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: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride
• 英文别名: (3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-ol hydrochloride；(3R,5S)-5-[hydroxy(diphenyl)methyl]pyrrolidin-3-ol;hydrochloride
• CAS: 1173184-14-9
• 化学式: C₁₇H₁₉NO₂*ClH
• 分子量: 305.804
• InChiKey: OTNNAKLSHPDKQS-RCPFAERMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.49
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 3-(5-(((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yl)oxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide
  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
• 作为产物：
  描述：

  (3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-ol 在 盐酸 作用下， 以 水 为溶剂， 以32.1 g的产率得到trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride
  参考文献：
  名称：

  A General Approach for Preparation of Polymer-Supported Chiral Organocatalysts via Acrylic Copolymerization

  摘要：

  Polymer-supported chiral organocatalysts, as well as most other forms of immobilized catalysts! arc traditionally prepared by a postmodification approach where modified catalyst precursors are anchored onto prefabricated polymer beads. Herein, we report an alternative and more scalable approach where polymer-supported chiral enamine and iminium organocatalysts are prepared in a bottom-up fashion where methacrylic functional monomers are prepared in an entirely nonchromatographic manner and subsequently copolymerized with suitable comonomers to give cross-linked polymer beads. All syntheses have been conducted on multigram scale for all intermediates and finished polymer products, and the catalysts have proven successful in reactions taking place in solvents spanning a wide range of solvent polarity. While polymer-supported proline and proline-amides generally demonstrated excellent results and recycling robustness in asymmetric aldol reactions or ketones and benzaldehydes, the simplest type of Jorgensen/Hayashi diarylprolinol TMS-ether showed excellent selectivity, but rather sluggish reactivity in the Enders-type asymmetric cascade. The polymer-supported version of the first-generation MacMillan imidazolidinone had a pattern of reactivity very similar to that of the monomeric catalyst, but is too unstable to allow recycling.

  DOI：

  10.1021/jo902585j

文献信息

• A heterogeneous layered bifunctional catalyst for the integration of aerobic oxidation and asymmetric C–C bond formation
  作者：Hiroyuki Miyamura、Gerald C. Y. Choo、Tomohiro Yasukawa、Woo-Jin Yoo、Shu Kobayashi

  DOI：10.1039/c3cc46204h

  日期：——

  The design and synthesis of a heterogeneous bifunctional chiral catalyst for the sequential aerobic oxidation–asymmetric Michael reactions between primary allylic alcohols and dibenzyl malonate are described. Interestingly, we found that layering bimetallic nanoparticles over the organocatalyst, within the chiral composite material, is crucial for catalytic activity.

  报道了用于一级烯丙醇与二苄基丙二酸酯顺序氧气氧化-不对称迈克尔反应的非均相双功能手性催化剂的设计与合成。有趣的是，我们发现将双金属纳米粒子层叠在手性复合材料中的有机催化剂上，对催化活性至关重要。