3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester | 252053-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: N-tert-butoxycarbonyl-3-phthalimidopiperidin-2-one；3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-piperidin-1-carboxylic acid tert-butyl ester；Tert-butyl 3-(1,3-dioxoisoindol-2-yl)-2-oxopiperidine-1-carboxylate
• CAS: 252053-41-1
• 化学式: C₁₈H₂₀N₂O₅
• 分子量: 344.367
• InChiKey: MBBLOKHODDKAFW-UHFFFAOYSA-N

物化性质

• 沸点：
  522.2±43.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 在 ruthenium(IV) oxide sodium periodate 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 3.33h， 生成 3'-fluorothalidomide
  参考文献：
  名称：

  (R)- and (S)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide

  摘要：

  3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation, In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-a production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.

  DOI：

  10.1021/ol9902172
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 3-phthalimidyl-piperidin-2-one 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 以92%的产率得到3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  (R)- and (S)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide

  摘要：

  3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation, In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-a production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.

  DOI：

  10.1021/ol9902172

文献信息

• Synthesis and Configurational Stability of (S)- and (R)-Deuteriothalidomides
  作者：Takeshi Yamamoto、Etsuko Tokunaga、Shuichi Nakamura、Norio Shibata、Takeshi Toru

  DOI：10.1248/cpb.58.110

  日期：——

  3'-Deuteriothalidomide was synthesized and found to be configurationally five times more stable than thalidomide toward racemization at physiological pH.

  合成了3'-氘代沙利度胺，在生理pH值条件下，其稳定度比沙利度胺稳定五倍。
• Asymmetric Synthesis of Both Mirror Images of 3′-Fluorothalidomide by Enantiodivergent Fluorination Using a Single, Cinchona Alkaloid
  作者：Takeshi Yamamoto、Yuka Suzuki、Emi Ito、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/ol102818g

  日期：2011.2.4

  Enantiomerically pure 3'-fluorothalidomide (2) was successfully synthesized by enantiodivergent electrophilic fluorination using a combination of cinchona alkaloids and N-fluorobenzenesulfonimide (NFSI) as the key reaction. Importantly, a single chiral molecule, dihydroquinine (DHQ), allowed access to the mirror image form of 3'-fluorothalidimide by the choice of additives. While the use of TMEDA gave fluorinated (S)-4, the precursor of 2, with 78% ee, Cu(acac)(2)/bipy, afforded the antipode, (R)-4, In 77% ee.
• (<i>R</i>)- and (<i>S</i>)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide
  作者：Yoshio Takeuchi、Tomoki Shiragami、Kenichi Kimura、Emiko Suzuki、Norio Shibata

  DOI：10.1021/ol9902172

  日期：1999.11.1

  3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation, In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-a production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.