tert-butyl N-(isopropyl)-L-alaninate | 150884-82-5

• 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: tert-butyl N-(isopropyl)-L-alaninate
• 英文别名: tert-butyl (2S)-2-(propan-2-ylamino)propanoate
• CAS: 150884-82-5
• 化学式: C₁₀H₂₁NO₂
• 分子量: 187.282
• InChiKey: QJDINOZQEIJTII-QMMMGPOBSA-N

物化性质

• 沸点：
  221.7±23.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(isopropyl)-L-alaninate 在 sodium tetrahydroborate 、 TEA 、 硫酸 、 sodium methylate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4S,5S)-1-isopropyl-5-methyl-4-hydroxy-2-oxopyrrolidine
  参考文献：
  名称：

  Diastereofacial selectivity in reduction of chiral tetramic acids

  摘要：

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.

  DOI：

  10.1021/jo00072a018
• 作为产物：
  描述：

  L-丙氨酸叔丁酯盐酸盐 、 丙酮 在 palladium on activated charcoal TEA 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以49%的产率得到tert-butyl N-(isopropyl)-L-alaninate
  参考文献：
  名称：

  Diastereofacial selectivity in reduction of chiral tetramic acids

  摘要：

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.

  DOI：

  10.1021/jo00072a018

文献信息

• [EN] CONJUGATES COMPRISING CELL-BINDING AGENTS AND CYTOTOXIC AGENTS<br/>[FR] CONJUGUÉS COMPRENANT DES AGENTS DE LIAISON CELLULAIRE ET DES AGENTS CYTOTOXIQUES
  申请人：IMMUNOGEN INC

  公开号：WO2016036794A1

  公开（公告）日：2016-03-10

  The invention relates to novel cell-binding agent-cytotoxic agent conjugates, wherein the cell-binding agent (CBA) is covalently linked to the cytotoxic agent through an aldehyde group obtained from oxidation of a 2-hydroxyethylamine moiety on the CBA. The invention also provides methods of preparing the conjugates of the present invention. The invention further provides composition and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the conjugates of the invention.

  该发明涉及一种新型细胞结合剂-细胞毒剂偶联物，其中细胞结合剂（CBA）通过氧化CBA上的2-羟乙胺基团得到的醛基与细胞毒剂共价连接。该发明还提供了制备本发明偶联物的方法。该发明还提供了使用该发明的偶联物抑制异常细胞生长或治疗哺乳动物增生性疾病的组合物和方法。
• US7468371B2
  申请人：——

  公开号：US7468371B2

  公开（公告）日：2008-12-23
• [EN] CYTOTOXIC BENZODIAZEPINE DERIVATIVES<br/>[FR] DÉRIVÉS DE BENZODIAZÉPINE CYTOTOXIQUE
  申请人：IMMUNOGEN INC

  公开号：WO2016036801A1

  公开（公告）日：2016-03-10

  The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepine compounds of formula (I)- (VI). The invention also provides conjugates of the benzodiazepine compounds linked to a cell-binding agent. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention.
• [EN] ANTI-CD 123 ANTIBODIES AND CONJUGATES AND DERIVATIVES THEREOF<br/>[FR] ANTICORPS ANTI-CD 123 ET CONJUGUÉS ET DÉRIVÉS CORRESPONDANTS
  申请人：IMMUNOGEN INC

  公开号：WO2017004026A1

  公开（公告）日：2017-01-05

  The present disclosure generally relates to antibodies, antigen-binding fragments thereof, polypeptides, and immunoconjugates that bind to CD 123 antigen (the a chain of the interleukine 3 receptor, or IL-3Ra). The present disclosure also relates to methods of using such CD123-binding molecules for diagnosing and treating diseases, such as B-cell malignancies.
• Diastereofacial selectivity in reduction of chiral tetramic acids
  作者：Nathalie Galeotti、Joel Poncet、Laurent Chiche、Patrick Jouin

  DOI：10.1021/jo00072a018

  日期：1993.9

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.