(3R,4R)-1-benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate | 136137-85-4

• 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: (3R,4R)-1-benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate
• 英文别名: 1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate；[(3R,4R)-4-acetyloxy-1-benzyl-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 136137-85-4
• 化学式: C₁₅H₁₅NO₆
• 分子量: 305.287
• InChiKey: MGGABTRPYQRCJY-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (3S,4S)-1-苄基吡咯烷-3,4-二醇
  参考文献：
  名称：

  Serra, M. Elisa Silva; Murtinho, Dina; Goth, Albertino, ARKIVOC, 2010, vol. 2010, # 5, p. 64 - 69

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R)-4-(N-benzylcarbamoyl)-2,3-diacetoxybutyric acid 在 盐酸 、 氢溴酸 作用下， 反应 41.0h， 生成 (3R,4R)-1-benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate
  参考文献：
  名称：

  Practical Synthesis of (R)-1-Benzyl-3-hydroxy-2,5-pyrrolidinedione and Its Acetate from L-Tartaric Acid

  摘要：

  DOI：

  10.3987/com-95-7301

文献信息

• Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant
  作者：Dnyaneshwar N Garad、Subhash D Tanpure、Santosh B Mhaske

  DOI：10.3762/bjoc.11.113

  日期：——

  efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.

  过硫酸铵-二甲基亚砜（APS-DMSO）已开发为一种高效的新型脱水剂，可用于方便的一锅法合成杂环状酰亚胺的便捷方法，从容易获得的伯胺和环状酸酐开始就可以高收率地合成。已经提出了涉及DMSO的可能的自由基机制。已经证明了这种简便的一锅式酰亚胺形成方法在实际合成vernakalant中的应用。
• Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles
  作者：Adriano S. Vieira、Fernando P. Ferreira、Pedro F. Fiorante、Rafael C. Guadagnin、Hélio A. Stefani

  DOI：10.1016/j.tet.2008.02.006

  日期：2008.4

  The stereoselective nucleophilic addition of potassium aryl- and alkynyltrifluoroborates to cyclic N-acyliminium ion derivatives from N-benzyl-3,4,5-triacetoxy-2-pyrrolidinone, affording the respective 5-substituted 2-pyrrolidinone is described. The products were obtained in moderate to good yields and with preference for the syn diastereomer.

  描述了将芳基-和炔基三氟硼酸钾立体选择性亲核加成到来自N-苄基-3,4,5-三乙酰氧基-2-吡咯烷酮的环状N-酰基亚胺离子衍生物上，得到各自的5-取代的2-吡咯烷酮。以中等至良好的产率获得产物，并且优选顺式非对映异构体。
• Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated <i>N</i>,<i>O</i>-Acetals Derived from <scp>l</scp>-Tartaric Acid
  作者：Abdelkhalek Ben Jamaa、Fabienne Grellepois

  DOI：10.1021/acs.joc.7b01814

  日期：2017.10.6

  substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal l-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product

  尽管存在高度吸电子的氟化取代基，但还是从氟化的O-乙酰基N，O-乙缩醛1-酒石酸衍生物成功生成了环状α-三氟甲基化的N-酰基亚胺离子。在这些中间体上以高至极高的合成力添加腈非对映选择性，并在大多数情况下导致恶唑啉和酰胺为单一非对映异构体。添加的非对映选择性和反应产物的性质取决于酒石酸支架的羟基上的取代基。该方法获得了对映纯的，高度官能化的5-（三氟甲基）吡咯烷-2-酮衍生物，其在四取代的碳上带有氟化取代基。
• Towards Simplifying the Chemistry of<i>N</i>-Acyliminium Ions: A One-Pot Protocol for the Preparation of 5-Acetoxy Pyrrolidin-2-ones and 2-Acetoxy<i>N</i>-Alkoxycarbonyl Pyrrolidines from Imides
  作者：Vincent Dalla、Fridrich Szemes Jr.、Anthony Fousse、Raja Ben Othman、Till Bousquet、Mohamed Othman

  DOI：10.1055/s-2006-926318

  日期：——

  A new one-step protocol for the synthesis of acetoxy lactams starting from imides has been developed. This method involves regiospecific reduction of the imide with LiEt 3 BH, then capture of the transient lithium alkoxide by acetic anhydride.

  已经开发了一种从酰亚胺开始合成乙酰氧基内酰胺的新一步法。该方法包括用 LiEt 3 BH 对酰亚胺进行区域特异性还原，然后用乙酸酐捕获瞬时的醇锂。
• Chiral cyclic imides with c2-symmetry. Novel reagents for the synthesis of optically pure lactones containing three contiguous tertiary centers
  作者：Hidemi Yoda、Koji Shirakawa、Kunihiko Takabe

  DOI：10.1016/s0040-4039(00)92719-9

  日期：1991.7

  Asymmetric reactions employing C2-symmetrical imides readily prepared from L-tartaric acid with Grignard reagents and sodium borohydride afforded a separable mixture of two hydroxyamides with high diastereoselectivity. Products were lactonized respectively to provide optically pure γ- alkylated lactones with contiguous tertiary carbon centers. The reaction mechanisms in asymmetric induction were also

  使用由L-酒石酸与Grignard试剂和氢硼化钠轻松制备的C 2-对称酰亚胺进行的不对称反应提供了具有高非对映选择性的两种羟酰胺的可分离混合物。将产物分别内酯化以提供具有连续的叔碳中心的光学纯的γ-烷基化内酯。还讨论了不对称诱导中的反应机理。