tert-butyl (S)-2-((1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate | 281197-55-5

• 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: tert-butyl (S)-2-((1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]pyrrolidine-1-carboxylate；(S)-2-[(1,3-dioxoisoindolin-2-yl)methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester；tert-butyl (2S)-2-[(1,3-dioxoisoindol-2-yl)methyl]pyrrolidine-1-carboxylate
• CAS: 281197-55-5
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: SCEDFTNTOAUUSL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-((1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate 在 甲胺 作用下， 以 乙醇 为溶剂， 以95%的产率得到S-叔丁氧羰基-2-(氨基乙基)吡咯烷
  参考文献：
  名称：

  Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

  摘要：

  A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.038
• 作为产物：
  描述：

  L-脯氨醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 tert-butyl (S)-2-((1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

  摘要：

  A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.038

文献信息

• Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts
  作者：Feng An、Biplab Maji、Elizabeth Min、Armin R. Ofial、Herbert Mayr

  DOI：10.1021/jacs.9b11877

  日期：2020.1.22

  the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale

  有机催化反应中常用的 32 种吡咯烷和咪唑烷酮的 Brønsted 碱度 pKaH（即共轭酸的 pKa）已在乙腈溶液中使用 CH 酸作为指示剂通过光度法测定。大多数研究的吡咯烷的碱性范围为 16 < pKaH < 20，而咪唑烷酮的碱性明显较低 (10 < pKaH < 12)。2-(三氟甲基)吡咯烷 (A14, pKaH 12.6) 和 2-咪唑鎓甲基取代的吡咯烷 A21 (pKaH 11.1) 超出了吡咯烷的典型范围，其碱度与咪唑烷酮的碱度相当。这 32 种有机催化剂与二苯甲基离子 (Ar2CH+) 和结构相关的醌甲基化物（用于量化亲核反应性的常见参考亲电试剂）的反应动力学已通过光度计测量。大多数反应遵循二级动力学，胺一级反应，亲电试剂一级反应。由于胺在亲电子试剂上的初始攻击的可逆性，随后中间体铵离子的速率决定性去质子化，观察到咪唑烷酮和几种携带大量 2-取代基的吡咯烷的反应更复杂的动力学。在
• Fluorescence polarization assays for binding of caspase inhibitors and probes therefor
  申请人：Dollings Paul

  公开号：US20070065898A1

  公开（公告）日：2007-03-22

  This invention provides a fluorescence polarization assay useful in the detection and evaluation of caspases inhibitors. This invention also provides novel fluorescent probes used in the fluorescence polarization assay, and methods for making the fluorescent probes, which have the Formula I: wherein the constituent variables are as defined herein.

  这项发明提供了一种用于检测和评估半胱氨酸蛋白酶抑制剂的荧光极化测定方法。该发明还提供了用于荧光极化测定的新型荧光探针，以及制备荧光探针的方法，其具有以下化学式：其中组成变量如本文所定义。
• Highly Enantioselective Michael Addition of Ketones to Nitroolefins with a Pyrrolidine-Based Phthalimide as an Enamine-Type Organocatalyst
  作者：Shu-rong Ban、Hong-yu Xie、Xi-xia Zhu、Qing-shan Li

  DOI：10.1002/ejoc.201101093

  日期：2011.11

  new type of pyrrolidine-based phthalimide and otheranalogous imide catalysts 5a–c were found to be efficient organocatalysts for the asymmetric Michael reaction of ketones to nitroalkenes. After fine optimization of solvents, temperature, and the additive, good to excellent enantioselectivities and diastereoselectivities (up to 99 % ee, up to >99:1 dr) can be achieved.

  发现一种新型的基于吡咯烷的邻苯二甲酰亚胺和其他类似的酰亚胺催化剂 5a-c 是酮不对称迈克尔反应生成硝基烯烃的有效有机催化剂。在对溶剂、温度和添加剂进行精细优化后，可以获得良好到出色的对映选择性和非对映选择性（高达 99% ee，高达 >99:1 dr）。
• Pyrimidodiazepinone derivative
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US07998954B2

  公开（公告）日：2011-08-16

  The invention provides a pyrimidodiazepinone derivative represented by the general formula (I) [wherein n represents 1 or 2, Z represents a hydrogen atom or the like, R1 and R2 may be the same or different, and each represents a hydrogen atom or the like, A represents a bond, (CH2)m (wherein m represents an integer of 1 to 4), optionally substituted phenylene, optionally substituted pyridinediyl, or C═O, R3 represents a hydrogen atom, optionally substituted lower alkyl, or the like, and R4 represents a hydrogen atom or the like], or a pharmaceutically acceptable salt thereof or the like.

  本发明提供了一种通式（I）所表示的嘧啶二氮杂环酮衍生物[其中n代表1或2，Z代表氢原子或类似物，R1和R2可以相同或不同，且每个代表氢原子或类似物，A代表键，(CH2)m（其中m表示1至4的整数），可选取代的苯基，可选取代的吡啶二基，或C═O，R3代表氢原子，可选取代的低碳基或类似物，且R4代表氢原子或类似物]，或其药学上可接受的盐或类似物。
• [EN] BENZIMIDAZOLE-LINKED INDOLE COMPOUND ACTING AS NOVEL DIVALENT IAP ANTAGONIST<br/>[FR] COMPOSÉ INDOLE LIÉ AU BENZIMIDAZOLE AGISSANT COMME NOUVEL ANTAGONISTE D'IAP DIVALENT<br/>[ZH] 作为新型二价IAP拮抗剂的苯并咪唑联吲哚化合物
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2017186147A1

  公开（公告）日：2017-11-02

  本发明公开了一类作为IAP拮抗剂的新型二价苯并咪唑联吲哚化合物，具体公开了式(I)所示化合物或其药学上可接受的盐。