1,3-bis(benzyloxymethyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one | 896141-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(benzyloxymethyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one
• 英文别名: 1,3-Bis[(benzyloxy)methyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carbaldehyde；2-oxo-1,3-bis(phenylmethoxymethyl)imidazole-4-carbaldehyde
• CAS: 896141-21-2
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: RSZJXJSELROYTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(benzyloxymethyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one 在 盐酸 、 calcium borohydrate (bistetrahydrofuran) 、 水 、 potassium hydrogen phthalate 、 manganese(III) triacetate dihydrate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三氟乙酸 、 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.25h， 生成 benzyl N-[[(5S,6R,7R)-6-(azidomethyl)-2-oxo-7-(2-oxo-1,3-dihydroimidazol-4-yl)-1,3-bis(phenylmethoxymethyl)-4,5,6,7-tetrahydrobenzimidazol-5-yl]methyl]carbamate
  参考文献：
  名称：

  Revisiting the Kinnel–Scheuer hypothesis for the biosynthesis of palau'amine

  摘要：

  在此，我们提出了帕劳胺的另一种生物合成途径，以解决最初的 KinnelâScheuer 假设中的立体化学问题。此外，我们还将这一修正后的假说作为实验室合成帕劳胺的指南。

  DOI：

  10.1039/c0cc02214d
• 作为产物：
  描述：

  1,3-bis(benzyloxymethyl)-4-(hydroxymethylene)-1,3-dihydro-imidazol-2-one 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到1,3-bis(benzyloxymethyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068

文献信息

• A Biomimetic Route for Construction of the [4+2] and [3+2] Core Skeletons of Dimeric Pyrrole–Imidazole Alkaloids and Asymmetric Synthesis of Ageliferins
  作者：Xiao Wang、Xiaolei Wang、Xianghui Tan、Jianming Lu、Kevin W. Cormier、Zhiqiang Ma、Chuo Chen

  DOI：10.1021/ja309172t

  日期：2012.11.14

  The pyrrole-imidazole alkaloids have fascinated chemists for decades because of their unique structures. The high nitrogen and halogen contents and the densely functionalized skeletons make their laboratory synthesis challenging. We describe herein an oxidative method for accessing the core skeletons of two classes of pyrrole-imidazole dimers. This synthetic strategy was inspired by the putative biosynthesis

  几十年来，吡咯-咪唑生物碱因其独特的结构而令化学家着迷。高氮和卤素含量以及密集功能化的骨架使其实验室合成具有挑战性。我们在此描述了一种用于访问两类吡咯-咪唑二聚体的核心骨架的氧化方法。这种合成策略受到假定的生物合成途径的启发，其发展得到了计算研究的促进。使用这种方法，我们已成功制备了天然对映体形式的ageliferin、bromoageliferin 和dibromoageliferin。
• A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
  作者：Paul J. Dransfield、Anja S. Dilley、Shaohui Wang、Daniel Romo

  DOI：10.1016/j.tet.2005.12.068

  日期：2006.5

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.
• Revisiting the Kinnel–Scheuer hypothesis for the biosynthesis of palau'amine
  作者：Zhiqiang Ma、Jianming Lu、Xiao Wang、Chuo Chen

  DOI：10.1039/c0cc02214d

  日期：——

  We propose herein an alternative biosynthetic pathway for palau'amine in order to resolve the stereochemical issue from the original Kinnel–Scheuer hypothesis. Furthermore, we use this revised hypothesis as a guide toward the laboratory synthesis of palau'amine.

  在此，我们提出了帕劳胺的另一种生物合成途径，以解决最初的 KinnelâScheuer 假设中的立体化学问题。此外，我们还将这一修正后的假说作为实验室合成帕劳胺的指南。