(R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione | 1312764-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione
• 英文别名: (R)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione；(3R)-3-hydroxy-1-[(4-methoxyphenyl)methyl]pyrrolidine-2,5-dione
• CAS: 1312764-95-6
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: MMPZOAJGGCUAFV-SNVBAGLBSA-N

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：

  (R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione 在 magnesium 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 (4R)-5-hydroxy-4-methoxy-1-[(4-methoxyphenyl)methyl]-5-[4-(oxan-2-yloxy)butyl]pyrrolidin-2-one
  参考文献：
  名称：

  Spiroaminal model systems of the marineosins with final step pyrrole incorporation

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.02.059
• 作为产物：
  描述：

  4-甲氧基苄胺 在 乙醇 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 50.0h， 生成 (R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  带有烯醛的内酰胺衍生物对Afford双环N-杂环的分子内曼尼希和迈克尔环化反应。

  摘要：

  已经开发了酸催化的分子内乙烯基曼尼希反应和分子内迈克尔反应，其从带有烯醛的羟基内酰胺衍生物提供吡咯烷酮稠合的N-杂环。取决于羟基内酰胺上的取代基，烯醛部分充当亲核试剂（即，作为烯醇/烯醇酸酯）或亲电子试剂，以分别与由羟基内酰胺部分生成的N-酰基亚胺离子或烯酰胺反应。在具有5至8元环的稠合N-杂环的构建中证明了反应。

  DOI：

  10.1021/acs.orglett.9b03210

文献信息

• Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence
  作者：Piotr Szcześniak、Sebastian Stecko、Elżbieta Maziarz、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1021/jo502146z

  日期：2014.11.7

  A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz’s reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky’s diene. The stereochemical course of the investigated reaction has been explained in detail

  描述了一种直接合成亚氨基糖的吲哚并立定和喹喔嗪骨架的方法。提出的策略是基于先用Schwartz试剂还原一锅糖内酰胺，然后再将得到的糖亚胺与Danishefsky的二烯进行非对映选择性的Mannich / Michael串联反应。已详细解释了所研究反应的立体化学过程。所获得的双环产物是用于合成各种天然存在的多羟基化生物碱及其衍生物的有吸引力的结构单元。
• Stereoselective synthesis of spirofuranone-γ-lactam core of cephalimysin A
  作者：Wuxia Zhang、Wenhao Zhu、Dehai Xiao、Bo Wang

  DOI：10.1016/j.tetlet.2018.07.036

  日期：2018.9

  Cephalimysin A is a potent anticancer natural product and its structure remains to be fully elucidated. To solve the stereochemical issue, a stereoselective synthesis of its spirofuranone-γ-lactam core was performed in a cascade fashion. The absolute configuration of key spiro stereogenic center was introduced based on d-malic acid derived imide and confirmed by a stereospecific derivatization.

  头孢菌素A是有效的抗癌天然产物，其结构仍有待充分阐明。为了解决立体化学问题，以级联方式进行了其螺呋喃酮-γ-内酰胺核的立体选择性合成。基于d-苹果酸衍生的酰亚胺引入了关键的螺旋立体异构中心的绝对构型，并通过立体特异性衍生化得到了证实。
• 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.
• 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.
• Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals To Afford Bicyclic N-Heterocycles
  作者：Yarkali Krishna、Kola Shilpa、Fujie Tanaka

  DOI：10.1021/acs.orglett.9b03210

  日期：2019.10.18

  Acid-catalyzed intramolecular vinylogous Mannich reactions and intramolecular Michael reactions affording pyrrolizinone-fused N-heterocycles from hydroxylactam derivatives bearing enals have been developed. Depending on the substituent on the hydroxylactam, the enal moiety acted either as a nucleophile (i.e., as an enol/enolate) or as an electrophile to react with the N-acyliminium ion or enamide generated

  已经开发了酸催化的分子内乙烯基曼尼希反应和分子内迈克尔反应，其从带有烯醛的羟基内酰胺衍生物提供吡咯烷酮稠合的N-杂环。取决于羟基内酰胺上的取代基，烯醛部分充当亲核试剂（即，作为烯醇/烯醇酸酯）或亲电子试剂，以分别与由羟基内酰胺部分生成的N-酰基亚胺离子或烯酰胺反应。在具有5至8元环的稠合N-杂环的构建中证明了反应。