(3S,4S)-3,4-Dimethoxy-3,4-dihydro-2H-pyrrole 1-oxide | 150638-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3S,4S)-3,4-Dimethoxy-3,4-dihydro-2H-pyrrole 1-oxide
• 英文别名: (3S,4S)-3,4-dimethoxy-1-oxido-3,4-dihydro-2H-pyrrol-1-ium
• CAS: 150638-40-7
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: SGCYKIZSMPYTHV-WDSKDSINSA-N

物化性质

• 沸点：
  320.9±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-Dimethoxy-3,4-dihydro-2H-pyrrole 1-oxide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-1-((2S,3S,4S)-3,4-dimethoxy-1-oxy-3,4-dihydro-2H-pyrrol-2-yl)-5-phenyl-heptan-2-ol
  参考文献：
  名称：

  Acceleration of hetero-Michael reaction by symmetrical pentacyclic guanidines

  摘要：

  Symmetrical pentacyclic guanidines 1a-c and 2 which contain the core skeleton of 13,14,15-isocrmbescidine 800, have been synthesized. In the presence of catalytic amounts of these guanidines 1, the reaction rate of the conjugate addition of pyrrolidine (9) to gamma -crotonolactone (10) could be enhanced depending upon the size of the cavities and substituents on tetrahydropyran rings of 1 and 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00907-3
• 作为产物：
  描述：

  (+)-(2S,3S)-1,4-Bis(tosyloxy)-2,3-dimethoxybutane 在 盐酸羟胺 、 三乙胺 、 mercury(II) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (3S,4S)-3,4-Dimethoxy-3,4-dihydro-2H-pyrrole 1-oxide
  参考文献：
  名称：

  New synthesis of five-membered cyclic nitrones from tartaric acid

  摘要：

  DOI：

  10.1021/jo00071a045

文献信息

• 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.