Tert-butyl 2-[(4-chlorophenyl)methylideneamino]-4-methylpentanoate | 287184-51-4

• 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: Tert-butyl 2-[(4-chlorophenyl)methylideneamino]-4-methylpentanoate
• CAS: 287184-51-4
• 化学式: C₁₇H₂₄ClNO₂
• 分子量: 309.836
• InChiKey: NXKDDJPFWNYJNY-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±27.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[(4-chlorophenyl)methylideneamino]-4-methylpentanoate 、 1-氯-3-碘丙烷 在 (11bR)-(–)-4,4-二丁基-4,5-二氢-2,6-双(3,4,5-三氟苯基)-3H-二萘[2,1-c:1′,2′-e]氮杂卓溴化物 、 cesiumhydroxide monohydrate 、 盐酸 、 水 、 sodium carbonate 作用下， 以 甲苯 、 乙酸乙酯 、 水 为溶剂， 反应 15.0h， 以94%的产率得到tert-butyl (S)-2-isobutylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Catalytic asymmetric synthesis of cyclic α-alkyl-amino acid derivatives by C,N-double alkylation

  摘要：

  Catalytic asymmetric synthesis of various cyclic alpha-alkyl-amino acid derivatives having a tetrasubstituted alpha-carbon, such as alpha-alkylprolines has been accomplished by asymmetric phase-transfer C-alkylation of alpha-alkyl-amino acid derivatives and subsequent intramolecular N-alkylation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.105
• 作为产物：
  描述：

  亮氨酸叔丁酯 、 4-氯苯甲醛 生成 Tert-butyl 2-[(4-chlorophenyl)methylideneamino]-4-methylpentanoate
  参考文献：
  名称：

  Optically active quarternary ammonium salt with axial chirality, method for producing thereof, and application thereof for asymmetric synthesis of &agr;-amino acid

  摘要：

  提供一种具有轴向手性的新型光学活性季铵盐。该季铵盐可以作为相转移催化剂，通过立体选择性地烷基化甘氨酸衍生物，将其转化为光学活性的α-氨基酸衍生物。此外，根据本发明，可以生产用于制备新型季铵盐的有用中间体。

  公开号：

  US06340753B1

文献信息

• Phase-Transfer-Catalyzed Asymmetric S_NAr Reaction of α-Amino Acid Derivatives with Arene Chromium Complexes
  作者：Seiji Shirakawa、Kenichiro Yamamoto、Keiji Maruoka

  DOI：10.1002/anie.201409065

  日期：2015.1.12

  zed asymmetric SNAr reactions provide unique contribution to the catalytic asymmetric α‐arylations of carbonyl compounds to produce biologically active α‐aryl carbonyl compounds, the electrophiles were limited to arenes bearing strong electron‐withdrawing groups, such as a nitro group. To overcome this limitation, we examined the asymmetric SNAr reactions of α‐amino acid derivatives with arene chromium

  尽管相转移催化的不对称S N Ar反应为羰基化合物的催化不对称α-芳基化反应产生了生物活性的α-芳基羰基化合物做出了独特贡献，但亲电试剂仅限于带有强吸电子基团的芳烃，例如硝基。为了克服这一局限性，我们研究了α-氨基酸衍生物与衍生自氟代芳烃的芳烃铬配合物（包括含给电子取代基的芳烃铬配合物）的不对称S N Ar反应。联萘改性的手性相转移催化剂可有效地促进芳基化反应，从而生成相应的α，α-二取代的α-氨基酸，其中包含具有高对映选择性的各种芳族取代基。
• Catalytic asymmetric synthesis of cyclic α-alkyl-amino acid derivatives having a tetrasubstituted α-carbon
  作者：Yong-Gang Wang、Haruka Mii、Taichi Kano、Keiji Maruoka

  DOI：10.1016/j.bmcl.2009.04.025

  日期：2009.7

  Catalytic asymmetric synthesis of various cyclic alpha-alkyl-amino acid derivatives having a tetrasubstituted alpha-carbon has been accomplished by the utilization of phase-transfer alkylation of alpha-alkyl-amino acid derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Optically active quarternary ammonium salt with axial chirality, method for producing thereof, and application thereof for asymmetric synthesis of &agr;-amino acid
  申请人：Nagase & Co., Ltd.

  公开号：US06340753B1

  公开（公告）日：2002-01-22

  A novel optically active quarternary ammonium salt with an axial chirality is provided. The quarternary ammonium salt can act as a phase-transfer catalyst to convert glycine derivatives into optically active &agr;-amino acid derivatives by stereoselectively alkylating the glycine derivatives. Furthermore, according to the present invention, intermediates useful for producing the novel quarternary ammonium can be produced.

  提供一种具有轴向手性的新型光学活性季铵盐。该季铵盐可以作为相转移催化剂，通过立体选择性地烷基化甘氨酸衍生物，将其转化为光学活性的α-氨基酸衍生物。此外，根据本发明，可以生产用于制备新型季铵盐的有用中间体。
• Catalytic asymmetric synthesis of cyclic α-alkyl-amino acid derivatives by C,N-double alkylation
  作者：Taichi Kano、Ryu Sakamoto、Haruka Mii、Yong-Gang Wang、Keiji Maruoka

  DOI：10.1016/j.tet.2010.01.105

  日期：2010.6

  Catalytic asymmetric synthesis of various cyclic alpha-alkyl-amino acid derivatives having a tetrasubstituted alpha-carbon, such as alpha-alkylprolines has been accomplished by asymmetric phase-transfer C-alkylation of alpha-alkyl-amino acid derivatives and subsequent intramolecular N-alkylation. (C) 2010 Elsevier Ltd. All rights reserved.