N-phthaloylphenylglycine | 29618-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phthaloylphenylglycine
• 英文别名: N-phthaloylphenylglycine ethyl ester；N-Phthaloyl-D,L-phenylglycinethylester；phenyl-phthalimido-acetic acid ethyl ester；Ethyl 2-(1,3-dioxoisoindolin-2-yl)-2-phenylacetate；ethyl 2-(1,3-dioxoisoindol-2-yl)-2-phenylacetate
• CAS: 29618-32-4
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: FWGHEOIWJSULEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phthaloylphenylglycine 在 正丁基锂 、 过氯酰氟 作用下， 生成 α-fluoro-N-phthaloylphenylglycine ethyl ester
  参考文献：
  名称：

  Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination

  摘要：

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.

  DOI：

  10.1021/jo00059a036
• 作为产物：
  描述：

  2-(1-phenyl-vinyl)-isoindole-1,3-dione 、 C₁₄H₁₃O₄Si^(1-)*C₁₂H₂₄O₆*K⁽¹⁺⁾ 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以67%的产率得到N-phthaloylphenylglycine
  参考文献：
  名称：

  一种光催化合成N-烷基邻苯二甲酰亚胺的方法

  摘要：

  本发明提供了一种光催化合成N‑烷基邻苯二甲酰亚胺的方法，包括以下步骤：S1：往具有搅拌子的反应管中加入N‑烯基邻苯二甲酰亚胺和光敏剂Ir[dF(CF3)ppy]2(dtbbpy)PF6，之后将自由基前体烷基硅加入至所述反应管中；S2：加入二甲基亚砜至所述反应管中，将反应管抽空并换氮后，置于9W的蓝光LED灯下照射，并搅拌后，用乙酸乙酯和水稀释反应液，然后用乙酸乙酯萃取；S3：将萃取得到的有机相合并后，用无水硫酸钠干燥，再次过滤后，得到有机相溶液，经旋转蒸发仪除去溶剂；然后再用石油醚和乙酸乙酯的混合液作为淋洗剂进行柱层析分离，最后经旋转蒸发仪蒸馏得到产物N‑烷基邻苯二甲酰亚胺。通过本发明能够高效地制备N‑烷基邻苯二甲酰亚胺，生产效率高，副产物少。

  公开号：

  CN114671796A

文献信息

• Electrophilic Fluorination Mediated by Cinchona Alkaloids: Highly Enantioselective Synthesis of α-Fluoro-α-phenylglycine Derivatives
  作者：Barbara Mohar、Jérôme Baudoux、Jean-Christophe Plaquevent、Dominique Cahard

  DOI：10.1002/1521-3773(20011119)40:22<4214::aid-anie4214>3.0.co;2-b

  日期：2001.11.19

  A decisive step forward: A one-step fluorination on modified cinchona alkaloids produced a new range of enantiopure fluorinating agents that display high enantioselectivities in electrophilic fluorination. The first enantioselective synthesis of N-protected α-fluorophenylglycine derivatives was achieved with an enantiomeric excess up to 94 % [Eq. (a); R=Et, CN; HMDS=hexamethyldisilazanide].

  向前迈出了决定性的一步：在修饰的金鸡纳生物碱上进行一步氟化，产生了一系列新的对映纯氟化剂，它们在亲电氟化中显示出高对映选择性。N-保护的α-氟苯基甘氨酸衍生物的首次对映选择性合成的对映体过量最高为94％。（一种）; R = Et，CN；HMDS ＝六甲基二硅氮杂]。
• CHIRAL FLUORINATING REAGENTS
  申请人：ISIS INNOVATION LIMITED

  公开号：US20150284401A1

  公开（公告）日：2015-10-08

  This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.

  本发明涉及氟化剂，更具体地涉及手性非外消旋氟化剂，可用于对映选择性氟化，以及它们的合成、使用和其他相关主题。该氟化剂基于取代的1,4-二氮杂双环[2.2.2]辛烷（DABCO）骨架，并提供电子亲和性氟的对映选择性。
• US9701684B2
  申请人：——

  公开号：US9701684B2

  公开（公告）日：2017-07-11
• [EN] CHIRAL FLUORINATING REAGENTS<br/>[FR] RÉACTIFS DE FLUORATION CHIRAUX
  申请人：ISIS INNOVATION

  公开号：WO2014068341A2

  公开（公告）日：2014-05-08

  This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.
• Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination
  作者：Yoshio Takeuchi、Noriaki Itoh、Toshihiro Satoh、Toru Koizumi、Kentaro Yamaguchi

  DOI：10.1021/jo00059a036

  日期：1993.3

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.