(R)-N-phenylpantolactam | 169221-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-N-phenylpantolactam
• 英文别名: (R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one；(R)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone；2-Pyrrolidinone, 3-hydroxy-4,4-dimethyl-1-phenyl-, (3R)-；(3R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one
• CAS: 169221-13-0
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: JJZWNUSNHASPHA-JTQLQIEISA-N

物化性质

• 沸点：
  405.5±38.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-phenylpantolactam 在 4-二甲氨基吡啶 、 苄基三乙基氯化铵 、 N,N'-二环己基碳二亚胺 、 cesium fluoride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 76.0h， 生成 (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate
  参考文献：
  名称：

  Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

  摘要：

  Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3'R)- or (3S,3'S)-nitro esters with > 98:2 dr after column chromatography. Hydrolysis of the resulting diastereopure nitro esters gave the corresponding enantiopure nitro acids, which were readily converted in high yields into either (R)- or (S)-baclofen hydrochloride. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.021
• 作为产物：
  描述：

  (R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate 在 lithium hydroxide 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 29.0h， 生成 (R)-N-phenylpantolactam
  参考文献：
  名称：

  Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

  摘要：

  Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3'R)- or (3S,3'S)-nitro esters with > 98:2 dr after column chromatography. Hydrolysis of the resulting diastereopure nitro esters gave the corresponding enantiopure nitro acids, which were readily converted in high yields into either (R)- or (S)-baclofen hydrochloride. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.021

文献信息

• (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of α-hydroxy acids
  作者：Pelayo Camps、Francesc Pérez、Núria Soldevilla

  DOI：10.1016/s0957-4166(97)00176-6

  日期：1997.6

  Rac-α-bromo acids, rac-4, have been converted into (R)- or (S)-α-hydroxy acid, (R)- or (S)-9, by DCC-induced esterification with the chiral auxiliaries (R)- or (S)-1, followed by reaction with sodium p-methoxyphenoxide in the presence of tetra-n-hexylammonium iodide, conditions of dynamic kinetic resolution, to give quite diastereoselectively the (αR,3S)- or esters, 7, which were then oxidized with

  Rac - α-溴酸rac-4已通过DCC诱导与手性助剂的酯化反应转化为（R）-或（S）-α-羟基酸（R）-或（S）-9 （ R）-或（S）-1 ，然后在动态动力学拆分条件下，在碘化四-正己基铵盐存在下与对甲氧基苯甲酸钠反应，以非对映选择性生成（αR，3S）-或酯7然后将其用硝酸铈铵氧化，并在控制的酸性条件下水解。
• Cholesterol–diaryl ketone stereoisomeric dyads as models for “clean” type I and type II photooxygenation mechanisms
  作者：Inmaculada Andreu、Isabel M. Morera、Francisco Boscá、Laura Sanchez、Pelayo Camps、Miguel A. Miranda

  DOI：10.1039/b718068c

  日期：——

  Cholesterol (Ch) is a major target for oxidative degradation in cell membranes, a process which can occur by two mechanisms: Type I (via free radicals) and Type II (mediated by 1O2). In the present work, several dyads have been synthesized from β- and α-Ch and ketoprofen (KP) or tiaprofenic acid (TPA). Upon irradiation under anaerobic conditions, KP–α-Ch dyads were efficiently photolyzed, via intramolecular hydrogen abstraction from C-7. By contrast, KP–β-Ch, TPA–α-Ch, and TPA–β-Ch remained unchanged after prolonged irradiation. The transient absorption spectra of KP–α-Ch were assigned to the short-lived biradicals resulting from intramolecular hydrogen abstraction. Interestingly, the spectra and lifetimes obtained for the TPA-derived dyads were very similar to those of the TPA triplet excited state. For the KP–α-Ch dyads, generation of singlet oxygen was expectedly negligible. Conversely, for TPA–α-Ch a ΦΔ value as high as 0.5 was determined. Thus, KP-based dyads are appropriate models for clean type I Ch oxidation, whereas the TPA derivatives are suitable systems for investigation of the purely type II process.

  胆固醇（Ch）是细胞膜中氧化降解的主要目标，这一过程可以通过两种机制发生：I型（通过自由基）和II型（通过1O2介导）。在本工作中，已从β-和α-Ch以及酮洛芬（KP）或噻洛芬酸（TPA）合成了几种二元组。在厌氧条件下照射下，KP-α-Ch二元组通过C-7的分子内氢提取高效光裂解。相比之下，KP-β-Ch、TPA-α-Ch和TPA-β-Ch在长时间照射后保持不变。KP-α-Ch的瞬态吸收光谱归因于由分子内氢提取产生的短寿命双自由基。有趣的是，从TPA衍生的二元组获得的光谱和寿命与TPA三重激发态非常相似。对于KP-α-Ch二元组，预计单线态氧的生成可以忽略不计。相反，对于TPA-α-Ch，测得的ΦΔ值高达0.5。因此，基于KP的二元组是清洁型I Ch氧化的适当模型，而TPA衍生物是研究纯型II过程的合适系统。
• Synthesis of enantiomeric bridgehead substituted bisnoradamantane derivatives
  作者：Carles Ayats、Pelayo Camps、Mercè Font-Bardia、Xavier Solans、Santiago Vázquez

  DOI：10.1016/j.tet.2007.05.061

  日期：2007.8

  The preparation of (+)- and (−)-12 by resolution of (±)-12 with (R)-N-phenylpantolactam, (R)-13, is described. From (+)- and (−)-12 a series of chiral bisnoradamantane derivatives, whose chirality stems from substitution at the bridgehead positions, have been obtained in both enantiomeric forms.

  的制备（+） -和（ - ） - 12由（±）的分辨率- 12用（- [R ）- ñ -phenylpantolactam，（- [R ） - 13，进行说明。从（+）-和（-）- 12中，以两种对映体形式获得了一系列手性双降金刚烷衍生物，其手性来自桥头位置的取代。
• (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, new chiral auxiliaries for the asymmetric synthesis of α-arylpropanoic acids
  作者：Pelayo Camps、Sílvia Giménez

  DOI：10.1016/0957-4166(95)00110-b

  日期：1995.4

  rac-α-arylpropanoyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone(R)- and (S)-1, in the presence of triethylamine, under standard esterification conditions, gave (R,R)- and (S,S)-3, respectively, with high diastereoselectivity. Controlled acidic hydrolysis afforded the corresponding (R)- or (S)-α-arylpropanoic acids with high enantioselectivity, the chiral auxiliary being recovered

  rac-α-芳基丙酰氯与（R）-和（S）-3-羟基-4,4-二甲基-1-苯基-2-吡咯烷酮（R）-和（S）-1的反应在在标准酯化条件下，三乙胺分别得到（R，R）-和（S，S）-3 ，具有高非对映选择性。受控的酸性水解得到具有高对映选择性的相应的（R）-或（S）-α-芳基丙酸，手性助剂被有效地回收。
• (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in Diels–Alder reactions
  作者：Pelayo Camps、Mercè Font-Bardia、Sı́lvia Giménez、Francesc Pérez、Xavier Solans、Núria Soldevilla

  DOI：10.1016/s0957-4166(99)00267-0

  日期：1999.8

  the chiral auxiliaries (R)- and/or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (4, 17, 25 and 26, respectively) with different dienes [cyclopentadiene 5, isoprene 8, 11,12-dimethylene-9,10-dihydro-9,10-ethanoanthracene 9 and anthracene 10], catalyzed by titanium tetrachloride, is described. Cyclopentadiene gave adducts with esters (R)- or (S)-4 and (R)-25 with high endo- and facial-diastereoselectivities

  丙烯酸，甲基丙烯酸，反丁烯酸和反肉桂酸酯与手性助剂（R）和/或（S）-3-羟基-4,4-二甲基-的酯的Diels-Alder反应研究1-苯基-2-吡咯烷酮（4，17，25和26，分别地）具有不同的二烯[环戊二烯5，异戊二烯8，11,12-二亚甲基-9,10-二氢-9,10- ethanoanthracene 9和蒽10 ]描述了用四氯化钛催化。环戊二烯与酯（R）-或（S）-形成加合物4和（R）-25具有高的内-和面-非对映选择性。二烯5与（±）-17反应而没有内-非对映选择性，并且未能得到具有（±）-26的环加合物。异戊二烯仅与具有高面部非对映选择性的酯（S）-4反应。9与（R）-4的反应失败，因为二烯在酸性反应条件下不稳定。10和酯（S）-4的加成物（R）-17可以以高的面部非对映选择性获得。由酯（R）-或（S）-4和（R）-25衍生的加合物的LiOH水解得到相应的对映体纯酸，手性助剂被