3-ethoxyl-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione | 335646-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ethoxyl-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione
• 英文别名: 3-ethoxy-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione；3-ethoxy-4-[(2S)-2-[hydroxy(diphenyl)methyl]pyrrolidin-1-yl]cyclobut-3-ene-1,2-dione
• CAS: 335646-02-1
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: ZBORSFJREWQZMA-SFHVURJKSA-N

物化性质

• 沸点：
  561.2±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-ethoxyl-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione 在 sodium hydrogensulfide 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 3-methylthio-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  手性方型四氢萘酚：硼烷不对称还原前手性酮的新型配体

  摘要：

  合成了一系列在手性环的C（3）上具有N，S取代基的手性双官能方型脯氨醇配体，并将其应用于通过原位形成的手性硼杂环的不对称硼烷还原手性酮的硼烷，从而提供了高收率的仲醇和出色的对映体过量（高达99％）。获得了5a的晶体结构，并探讨了催化不对称还原的机理。

  DOI：

  10.1016/s0957-4166(01)00333-0
• 作为产物：
  描述：

  (S)-(+)-alpha,alpha-二苯基脯氨醇 、 方酸二乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 3-ethoxyl-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  用于将单酮和二酮高度对映选择性加成到硝基烯烃的新型双功能手性方酸酰胺-胺催化剂

  摘要：

  通过吡咯烷和金鸡纳生物碱的合理组合开发了新型双功能手性方酸酰胺-胺有机催化剂。该催化剂促进了单酮和二酮对广泛范围的硝基烯烃的对映选择性迈克尔加成，以中等至高产率提供相应的产物，具有优异的对映选择性和非对映选择性（产率高达 96%，96% ee，98:2 dr）。条件温和。这些结果表明，将两个手性特权骨架、吡咯烷和辛可宁与方酸酰胺连接器组装在一起是实现更广泛底物范围、高反应效率和对映选择性的有用策略。嵌入催化剂的两个主链之间手性的匹配对于提高对映选择性也很关键。

  DOI：

  10.3998/ark.5550190.0012.927

文献信息

• Design, synthesis and structure of new chiral squaric acid monoaminoalcohols and diaminoalcohols and their use as catalysts in asymmetric reduction of ketones and diketones
  作者：Hai-Bing Zhou、Ji Zhang、Shou-Mao Lü、Ru-Gang Xie、Zhong-Yuan Zhou、Michael C.K Choi、Albert S.C Chan、Teng-Kuei Yang

  DOI：10.1016/s0040-4020(01)00936-x

  日期：2001.11

  Many chiral squaric acid aminoalcohols and C2-symmetric diaminoalcohols have been synthesized and their in situ formed chiral boron heterocycles have been used as catalysts for the enantioselective reduction of prochiral ketones and diketones by borane to give alcohols with up to 99% enantiomeric excess and 99% yield. The effects of solvent, catalyst–substrate ratio and temperature were also investigated

  已经合成了许多手性方酸氨基醇和C 2对称的二氨基醇，它们的原位形成的手性硼杂环已被用作催化剂，通过硼烷对手性酮和二酮进行对映选择性还原，制得对映体过量高达99％的醇和99 ％ 屈服。还研究了溶剂，催化剂-底物比例和温度的影响。
• Chiral monoaminoalcohols and diaminoalcohols of squaric acid: new catalysts for the asymmetric reduction of ketones by borane
  作者：Haibing Zhou、Shoumao Lü、Rugang Xie、Albert S.C Chan、Teng-Kuei Yang

  DOI：10.1016/s0040-4039(00)02162-6

  日期：2001.2

  Two series of new chiral ligands, squaric acid aminoalcohols and C2-symmetric squaric acid diaminoalcohols have been synthesized. The chiral oxazaborolidines formed in situ from these ligands have been used in the enantioselective borane reduction of prochiral ketones and diketones to afford alcohol products with up to 99% enantiomeric excesses. The structures of the ligands have an obvious effect

  合成了两个系列的新手性配体，方酸氨基醇和C 2对称的方酸二氨基醇。由这些配体原位形成的手性恶唑硼烷已用于手性酮和二酮的对映选择性硼烷还原，以提供对映体过量高达99％的醇产物。配体的结构对所得醇的ee有明显影响。
• Novel bifunctional chiral squaramide-amine catalysts for highly enantioselective addition of mono and diketones to nitroalkenes
  作者：Ze Dong、Xiaoqing Jin、Pengcheng Wang、Chang Min、Jin Zhang、Zhe Chen、Hai-Bing Zhou、Chune Dong

  DOI：10.3998/ark.5550190.0012.927

  日期：——

  Novel bifunctional chiral squaramide–amine organocatalysts have been developed by rational combination of pyrrolidine and a cinchona alkaloid. The catalysts promoted the enantioselective Michael addition of both mono- and diketones to a broad range of nitroalkenes providing the corresponding products in moderate to high yields with excellent enantioselectivities and diastereoselectivities (up to 96%

  通过吡咯烷和金鸡纳生物碱的合理组合开发了新型双功能手性方酸酰胺-胺有机催化剂。该催化剂促进了单酮和二酮对广泛范围的硝基烯烃的对映选择性迈克尔加成，以中等至高产率提供相应的产物，具有优异的对映选择性和非对映选择性（产率高达 96%，96% ee，98:2 dr）。条件温和。这些结果表明，将两个手性特权骨架、吡咯烷和辛可宁与方酸酰胺连接器组装在一起是实现更广泛底物范围、高反应效率和对映选择性的有用策略。嵌入催化剂的两个主链之间手性的匹配对于提高对映选择性也很关键。
• A novel C3-symmetric prolinol-squaramide catalyst for the asymmetric reduction of ketones by borane
  作者：Xiang-Fei Wu、Chang Min、Enkhtsetseg Nyamzundui、Hai-Bing Zhou、Chune Dong

  DOI：10.1016/j.tetasy.2011.09.020

  日期：2011.9

  A novel C-3-symmetric prolinol-squaramide has been developed for the asymmetric reduction of ketones by borane. By using only 5 mol % catalyst la for the reaction, high yields and excellent enantioselectivities (up to 95% yield, 93% ee) were obtained. Moreover, la can be easily recovered by simple precipitation and re-used for four cycles without losing the selectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• Chiral squaric prolinols: a new type of ligand for the asymmetric reduction of prochiral ketones by borane
  作者：Ji Zhang、Hai-Bing Zhou、Shou-Mao Lü、Mei-Ming Luo、Ru-Gang Xie、Michael C.K. Choi、Zhong-Yuan Zhou、Albert S.C. Chan、Teng-Kuei Yang

  DOI：10.1016/s0957-4166(01)00333-0

  日期：2001.7

  prolinol ligands, having N, S substituents at C(3) of the squaric ring were synthesized and applied to the asymmetric borane reduction of prochiral ketones via an in situ formed chiral boron heterocycle, affording secondary alcohols with high yields and excellent enantiomeric excesses (up to 99%). The crystal structure of 5a was obtained and the mechanism of the catalytic asymmetric reduction is also

  合成了一系列在手性环的C（3）上具有N，S取代基的手性双官能方型脯氨醇配体，并将其应用于通过原位形成的手性硼杂环的不对称硼烷还原手性酮的硼烷，从而提供了高收率的仲醇和出色的对映体过量（高达99％）。获得了5a的晶体结构，并探讨了催化不对称还原的机理。