(3S,4S)-3,4-Bis(methoxymethoxy)-1-pyrroline N-Oxide | 137945-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (3S,4S)-3,4-Bis(methoxymethoxy)-1-pyrroline N-Oxide
• 英文别名: (3S,4S)-3,4-bis(methoxymethoxy)-1-oxido-3,4-dihydro-2H-pyrrol-1-ium
• CAS: 137945-73-4
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: OIZSAHGETAKAMI-YUMQZZPRSA-N

物化性质

• 沸点：
  357.1±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-Bis(methoxymethoxy)-1-pyrroline N-Oxide 在 硫酸 、 二氧化硫 作用下， 反应 96.0h， 以52%的产率得到(2S,3R)-4-amino-1,4-dideoxy-L-threose-1-sulfonic acid
  参考文献：
  名称：

  D系列和L系列氨基苏糖的合成和评估：五元环氨基糖比六元环糖更有效的糖苷酶抑制剂吗？

  摘要：

  环状D-和L-4-氨基苏糖分别由D-酒石酸乙酯和L-酒石酸乙酯合成。D-氨基苏糖是α-葡萄糖苷酶和α-甘露糖苷酶的有效抑制剂。从四个4-氨基-4-脱氧-四糖苷的糖苷酶抑制潜能，讨论了5元和6元环氨基糖的每个官能团对各种糖苷酶的结合贡献。

  DOI：

  10.1016/j.bmc.2007.03.073
• 作为产物：
  描述：

  (3S,4S)-3,4-Bis(methoxymethoxy)pyrrolidine 在 sodium tungstate 、 urea-hydrogen peroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以70%的产率得到(3S,4S)-3,4-Bis(methoxymethoxy)-1-pyrroline N-Oxide
  参考文献：
  名称：

  使用尿素-过氧化氢络合物（UHP）和金属催化剂将仲胺氧化为硝酮

  摘要：

  使用脲-过氧化氢络合物（UHP）和金属催化剂，在室温下，仲胺很容易被氧化为相应的硝酮。钨酸钠是数次运行中最有效的催化剂，在这些条件下可以耐受常见的保护基团。

  DOI：

  10.1016/0040-4039(95)00558-t

文献信息

• Oxidation of secondary amines to nitrones using urea-hydrogen peroxide complex (UHP) and metal catalysts
  作者：Enrico Marcantoni、Marino Petrini、Olga Polimanti

  DOI：10.1016/0040-4039(95)00558-t

  日期：1995.5

  Secondary amines can be readily oxidized to the corresponding nitrones using urea-hydrogen peroxide complex (UHP) and metal catalysts in methanol at room temperature. Sodium tungstate is the most effective catalyst in several runs and common protecting groups are tolerated in these conditions.

  使用脲-过氧化氢络合物（UHP）和金属催化剂，在室温下，仲胺很容易被氧化为相应的硝酮。钨酸钠是数次运行中最有效的催化剂，在这些条件下可以耐受常见的保护基团。
• Kinetic Resolution in 1,3-Dipolar Cycloaddition of Tartaric Acid-Derived Nitrones to 2,3-Dihydro-1-phenyl-1H-phospholes. An Enantioselective Approach to the 2,2'-Coupled Pyrrolidine-Phospholane Ring System
  作者：Alberto Brandi、Stefano Cicchi、Andrea Goti、Marek Koprowski、K. Michal Pietrusiewicz

  DOI：10.1021/jo00085a019

  日期：1994.3

  Enantiomerically pure five-membered ring nitrones derived from L-tartaric acid via C2-symmetric O,O'-protected 3,4-dihydroxy pyrrolidines undergo highly regio- and stereoselective cycloaddition reactions with racemic 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide and 1-sulfide. In all cases formation of only two diastereomeric cycloadducts is observed and their ratio (up to 10:1) is dependent on the size of the protecting groups in the nitrone and on the extent of conversion. The tricyclic cycloadducts feature 2,2'-connection of pyrrolidine and phospholane rings and six contiguous stereogenic centers of which three are created and the one at phosphorus is kinetically resolved during the cycloaddition process. It is established that in the studied kinetic resolutions the stereoselectivity factor 8 = k(S)/k(R) exceeds the value of 10 (up to 14) in the most favorable cases. In a properly tuned reaction both the diastereomeric cycloadducts and the enantiomerically enriched dihydrophosphole derivative can be simultaneously obtained in satisfactory chemical and optical yields.
• A nitrone-based approach to the enantioselective total synthesis of (-)-anisomycin
  作者：Roberto Ballini、Enrico Marcantoni、Marino Petrini

  DOI：10.1021/jo00030a051

  日期：1992.2
• Synthesis of Nitrones Using the Methyltrioxorhenium/Hydrogen Peroxide System
  作者：Robert W. Murray、Kaliappan Iyanar、Jianxin Chen、James T. Wearing

  DOI：10.1021/jo961252e

  日期：1996.11.15

  Secondary amines are oxidized by the methyltrioxorhenium/hydrogen peroxide system to the corresponding nitrones in excellent yield. The results provide a further example of the parallel between the chemistry of this metal system and that of the dioxiranes.
• Hydroxylated pyrrolizidines and indolizidines; synthesis using cycloaddition reactions of functionalized cyclic nitrones
  作者：Avril E. McCaig、Richard H. Wightman

  DOI：10.1016/s0040-4039(00)79269-0

  日期：1993.6

  Cycloaddition reactions of functionalised DELTA1-pyrroline-N-oxides have been used to prepare the hydroxylated pyrrolizidines 11 and 22, the indolizidine 16, and the iminoheptitol 12.