(S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide | 936337-63-2

• 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: (S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide
• 英文别名: tert-butyl-[4-[(2S)-2,5-dimethyl-1-oxido-3,4-dihydropyrrol-1-ium-2-yl]phenoxy]-dimethylsilane
• CAS: 936337-63-2
• 化学式: C₁₈H₂₉NO₂Si
• 分子量: 319.519
• InChiKey: DBCBOJHXNHIDBN-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 在 四丁基氟化铵 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 trans-(2S,5S)-2,5-bis(4-hydroxyphenyl)-2,5-dimethylpyrrolidin-1-oxyl
  参考文献：
  名称：

  Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides

  摘要：

  Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.

  DOI：

  10.1021/ol050401p
• 作为产物：
  描述：

  (4-((tert-butyldimethylsilyl)oxy)phenyl)magnesium bromide 、 (R)-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 在 水 、 氯化铵 、 copper(II) acetate monohydrate 、 氨 、 氧气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide
  参考文献：
  名称：

  新型手性液晶有机自由基化合物的制备及铁电性能

  摘要：

  我们合成了新的手性液晶（LC）有机自由基化合物 2 和 3，它们是先前报道的化合物 1 的衍生物，它们在介晶核中含有一个手性环状硝基氧单元和一个酯基，并对其铁电性能进行了研究。对映体富集的 (2S,5S)-2 和 (2S,5S)-3 显示出 SmC * 相，将它们的铁电特性如自发极化 (Ps) 和倾斜角 (θ) 与 (2S,5S) 进行了比较)-1。

  DOI：

  10.3987/com-09-s(s)64

文献信息

• Magnetic Properties of All-Organic Liquid Crystals Containing a Chiral Five-Membered Cyclic Nitroxide Unit within the Rigid Core
  作者：Naohiko Ikuma、Rui Tamura、Satoshi Shimono、Naoyuki Kawame、Osamu Tamada、Naoko Sakai、Jun Yamauchi、Yukio Yamamoto

  DOI：10.1002/anie.200460007

  日期：2004.7.12
• Preparation and Properties of<i>C</i>₂-Symmetric Organic Radical Compounds Showing Ferroelectric Liquid Crystal Properties
  作者：Naohiko Ikuma、Yoshiaki Uchida、Rui Tamura、Katsuaki Suzuki、Jun Yamauchi、Yoshio Aoki、Hiroyuki Nohira

  DOI：10.1080/15421400903065325

  日期：2009.9.3

  We have synthesized a new class of liquid crystalline (LC) organic radical compounds 2, which are the C-2-symmetric derivatives of the previously reported compounds 1 containing a chiral nitroxide unit and an ester group in the mesogen core, and their LC properties have been fully characterized. The enantiomerically enriched 2 showed N* and SmC* phases. Their LC phase transition behavior is similar to that of 1, whereas the ferroelectric properties of the SmC* phase of (2S,5S)-2 differed from those of (2S,5S)-1. We discuss the origin of this difference in terms of their molecular structures optimized by molecular orbital calculations.
• Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides
  作者：Naohiko Ikuma、Hirohito Tsue、Naoko Tsue、Satoshi Shimono、Yoshiaki Uchida、Kazuyoshi Masaki、Nagahisa Matsuoka、Rui Tamura

  DOI：10.1021/ol050401p

  日期：2005.4.1

  Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.
• Preparation and Ferroelectric Properties of New Chiral Liquid Crystalline Organic Radical Compounds
  作者：Rui Tamura、Naohiko Ikuma、Katsuaki Suzuki、Yoshiaki Uchida、Yoshio Aoki、Hiroyuki Nohira

  DOI：10.3987/com-09-s(s)64

  日期：——

  synthesized new chiral liquid crystalline (LC) organic radical compounds 2 and 3, which are the derivatives of the previously reported compounds 1 containing a chiral cyclic nitroxide unit and an ester group in the mesogen core, and their ferroelectric properties have been studied. The enantiomerically enriched (2S,5S)-2 and (2S,5S)-3 showed an SmC * phase for which their ferroelectric properties such as spontaneous

  我们合成了新的手性液晶（LC）有机自由基化合物 2 和 3，它们是先前报道的化合物 1 的衍生物，它们在介晶核中含有一个手性环状硝基氧单元和一个酯基，并对其铁电性能进行了研究。对映体富集的 (2S,5S)-2 和 (2S,5S)-3 显示出 SmC * 相，将它们的铁电特性如自发极化 (Ps) 和倾斜角 (θ) 与 (2S,5S) 进行了比较)-1。