(S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione | 254730-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione
• 英文别名: (S)-3-hydroxy-N-(4-methoxybenzyl)pyrrolidine-2,5-dione；(S)-N-p-methoxybenzylmalimide；(s)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione；(3S)-3-hydroxy-1-[(4-methoxyphenyl)methyl]pyrrolidine-2,5-dione
• CAS: 254730-06-8
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: MMPZOAJGGCUAFV-JTQLQIEISA-N

物化性质

• 熔点：
  114.5-115.5 °C
• 沸点：
  492.1±45.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione 在 palladium on activated charcoal 三乙基硅烷 、 三氟化硼乙醚 、 氢气 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 134.0h， 生成 (+)-(4S,5R)-4-hydroxy-5-(3'-hydroxypropyl)-1-(4-methoxybenzyl)-2-pyrrolidinone
  参考文献：
  名称：

  从（S）-苹果酸开始不对称合成（-）-（R）-吡咯烷A

  摘要：

  描述了从天然（S）-苹果酸开始的天然（-）-吡咯烷醇A的不对称合成。通过高度反式-非对映选择性还原烷基化方法建立了立体异构中心。串联碱基诱导的分子内酰胺N-取代和甲苯磺酸消除导致目标分子。

  DOI：

  10.1016/s0957-4166(99)00395-x
• 作为产物：
  描述：

  4-甲氧基苄胺 在 乙醇 、 乙酰氯 作用下， 生成 (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione
  参考文献：
  名称：

  A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides

  摘要：

  Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from alpha-hydroxyacids, via chiral cyclic alpha-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from alpha-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide la with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.012

文献信息

• 2-对氟苄基-3-羟基吡咯烷氨基酸及其制备方 法和抗癌活性研究
  申请人：天津药明康德新药开发有限公司

  公开号：CN103073473B

  公开（公告）日：2017-06-23

  本发明涉及2‑对氟苄基‑3‑羟基吡咯烷氨基酸及其制备方法和抗癌活性研究，主要解决目前该类化合物较少的技术问题。该类化合物具有的结构通式如图所示:其中，R=各种氨基酸，其中优选含芳环的氨基酸。其合成路线如下：本发明主要考察于吡咯烷2位引入吸电性的基团对该类化合物活性的影响。
• Facile Synthesis of 3‐Hydroxyglutamic Acids via Cyanation of Chiral <i>N</i>‐Acyliminium Cation Derived From (<i>S</i>)‐Malic Acid
  作者：Makoto Oba、Atsushi Mita、Yoshinori Kondo、Kozaburo Nishiyama

  DOI：10.1080/00397910500278446

  日期：2005.12

  (S)‐malic acid is described. The chiral cyclic imide derived from (S)‐malic acid was converted to an acetoxylactam by reduction with sodium borohydride followed by acetylation. The obtained acetoxylactam was treated with trimethylsilyl cyanide in the presence of boron trifluoride etherate to give the corresponding cyanolactam in high yield, even though the diastereoselectivity of the cyanation reaction was

  摘要描述了通过氰化衍生自 (S)-苹果酸的 N-acyliminium 中间体轻松合成 3-羟基谷氨酸。衍生自（S）-苹果酸的手性环状酰亚胺通过用硼氢化钠还原然后乙酰化转化为乙酰氧基内酰胺。所得乙酰氧基内酰胺在三氟化硼醚合物存在下用三甲基甲硅烷基氰化物处理以高产率得到相应的氰内酰胺，即使氰化反应的非对映选择性适中。氰内酰胺的非对映异构体可通过色谱分离并独立转化为 (2R,3S)- 和 (2S,3S)-3-羟基谷氨酸。
• Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups
  作者：Maëva M. Pichon、Fabien Stauffert、Luis G. Addante-Moya、Anne Bodlenner、Philippe Compain

  DOI：10.1002/ejoc.201800051

  日期：2018.4.9

  The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron‐withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

  在 PPh3 和吡啶的存在下，使用亚化学计量的分子碘可将 α 位的伯醇和仲醇直接脱氧为各种活化的吸电子基团，包括酮、酯、酰胺、酰亚胺和腈基。
• Spiroaminal model systems of the marineosins with final step pyrrole incorporation
  作者：Joseph D. Panarese、Leah C. Konkol、Cynthia B. Berry、Brittney S. Bates、Leslie N. Aldrich、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2013.02.059

  日期：2013.5

  In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in similar to 9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt. (C) 2013 Elsevier Ltd. All rights reserved.
• A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides
  作者：Jin-Li Zheng、Hui Liu、Yu-Feng Zhang、Wei Zhao、Jin-Shuan Tong、Yuan-Ping Ruan、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2011.01.012

  日期：2011.2

  Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from alpha-hydroxyacids, via chiral cyclic alpha-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from alpha-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide la with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step. (C) 2011 Elsevier Ltd. All rights reserved.