sodium salt of di-tert-butyl iminodicarboxylate

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: sodium salt of di-tert-butyl iminodicarboxylate
• 英文别名: NaNBoc2；NaN(Boc)2；sodium;1-[(2-methylpropan-2-yl)oxy]-N-[(2-methylpropan-2-yl)oxycarbonyl]methanimidate
• 化学式: C₁₀H₁₈NO₄*Na
• 分子量: 239.247
• InChiKey: LEHHSNPQAVFFIL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sodium salt of di-tert-butyl iminodicarboxylate 在 bis(η3-allyl-μ-chloropalladium(II)) sodium hydroxide 、 臭氧 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N,N-Di-tert-butoxycarbonylglycine methyl ester
  参考文献：
  名称：

  通过钯催化的烯丙基取代合成N-保护的氨基酯

  摘要：

  N-保护的烯丙胺是通过钯催化的相应的乙酸烯丙酯的烯丙基取代为一系列的氮亲核试剂而制备的。将如此形成的N-保护的烯丙基胺进行烯烃的氧化裂解，得到N-保护的氨基酸或酯。

  DOI：

  10.1016/0040-4039(93)88120-8

文献信息

• [EN] SUBSTITUTED GLYCINE DERIVATIVES FOR USE AS MEDICAMENTS<br/>[FR] DERIVES DE GLYCINE SUBSTITUES SERVANT DE MEDICAMENTS
  申请人：PFIZER LTD

  公开号：WO2004016583A1

  公开（公告）日：2004-02-26

  The compounds of formula (I) are substituted glycine derivatives useful in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, arthritis, neuropathological disorders, sleep disorders, visceral pain disorders and gastrointestinal disorders. Processes for the preparation of the final products and intermediates useful in the process are included. Pharmaceutical compositions containing one or more of the compounds are also included. Formula (I) wherein R' is hydroxycarbonyl, a carboxylic acid biostere or prodrug thereof; R3, R3a, R2 and R2a are independently selected from H, C1-C6 alkyl, and Cl-C6 alkoxy Cl-C6 alkyl.

  公式(I)的化合物是取代甘氨酸衍生物，可用于治疗癫痫、晕厥发作、运动减少、颅脑疾病、神经退行性疾病、抑郁症、焦虑症、恐慌症、疼痛、关节炎、神经病理学疾病、睡眠障碍、内脏疼痛疾病和胃肠疾病。包括用于制备最终产品和在过程中有用的中间体的方法。还包含含有一种或多种化合物的药物组合物。公式(I)中，R'是羟碳酰基，羧酸的生物立体异构体或前药；R3、R3a、R2和R2a独立地选自H、C1-C6烷基和Cl-C6烷氧基Cl-C6烷基。
• Enantioselective Iridium-Catalyzed Allylic Aminations of Allylic Carbonates with Functionalized Side Chains. Asymmetric Total Synthesis of (<i>S</i>)-Vigabatrin
  作者：Günter Helmchen、Christian Gnamm、Géraldine Franck、Nicole Miller、Timon Stork、Kerstin Brödner

  DOI：10.1055/s-0028-1083158

  日期：——

  Iridium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (S)-vigabatrin to be prepared via a very short route.

  已经探索了含有多种O-官能团的烯丙基碳酸酯的铱催化胺化。在无盐条件下使用二酰胺和芳胺可实现高度的区域选择性和对映选择性。结果使抗癫痫药（S）-氨己烯酸可以通过非常短的路线制备。
• Enantioselective Syntheses of 2,5-Disubstituted Pyrrolidines Based on Iridium-Catalyzed Allylic Aminations-Total Syntheses of Alkaloids from Amphibian Skins
  作者：Martin Gärtner、Robert Weihofen、Günter Helmchen

  DOI：10.1002/chem.201100649

  日期：2011.6.27

  A broadly applicable route to trans‐2,5‐disubstituted pyrrolidines has been developed. Key steps are an asymmetric iridium‐catalyzed allylic amination, a Suzuki–Miyaura coupling, and an intramolecular aza‐Michael addition. Enantiomeric excesses in the range of 93–99 % ee have been achieved. Total syntheses of the alkaloids (−)‐225 C, (+)‐ and (−)‐223 H (xenovenine), (+)‐223 AB, (+)‐195 B, and (+)‐223 R

  已经开发出广泛适用的反式-2,5-二取代吡咯烷酮的方法。关键步骤是不对称铱催化的烯丙基胺化，Suzuki-Miyaura偶联和分子内氮杂-Michael加成。对映体过量已达到93–99％ee的范围 。生物碱的全合成（ - ） - 225℃，（+） -和（ - ） - 223ħ（xenovenine），（+） - 223 AB，（+） - 195乙，和（+） - 223 - [R已作为应用程序进行。
• Ir-Catalyzed Asymmetric Allylic Substitutions with (Phosphoramidite)Ir Complexes-Resting States, Synthesis, and Characterization of Catalytically Active (π-Allyl)Ir Complexes
  作者：Stephanie Spiess、Jevgenij A. Raskatov、Christian Gnamm、Kerstin Brödner、Günter Helmchen

  DOI：10.1002/chem.200902065

  日期：2009.10.26

  (π‐Allyl)Ir complexes: A new and very simple one‐pot synthesis of (π‐allyl)Ir complexes derived from phosphoramidites L is presented (see scheme). Ready availability of the allyl complexes allowed resting states and other parameters of the Ir‐catalyzed allylic substitution to be determined.

  （π-烯丙基）Ir络合物：提出了一种新的非常简单的一锅合成亚磷酰胺L衍生的（π-烯丙基）Ir络合物的方法（参见方案）。烯丙基配合物的现成性使得可以确定Ir催化的烯丙基取代基的静止状态和其他参数。
• Ir-Catalysed Asymmetric Allylic Substitutions with Cyclometalated (Phosphoramidite)Ir Complexes-Resting States, Catalytically Active (π-Allyl)Ir Complexes and Computational Exploration
  作者：Jevgenij A. Raskatov、Stephanie Spiess、Christian Gnamm、Kerstin Brödner、Frank Rominger、Günter Helmchen

  DOI：10.1002/chem.200903465

  日期：2010.6.11

  Mechanistic aspects of allylic substitutions with iridium catalysts derived from phosphoramidites by cyclometalation were investigated. The determination of resting states by 31P NMR spectroscopy led to the conclusion that the cyclometalation process is reversible. A novel, one‐pot procedure for the preparation of (π‐ allyl)Ir complexes was developed, and these complexes were characterised by X‐ray

  研究了通过环金属化衍生自亚磷酰胺的铱催化剂进行烯丙基取代的机理。通过31 P NMR光谱法测定静止态得出的结论是环金属化过程是可逆的。开发了一种新颖的一锅法制备（π-烯丙基）Ir配合物，并通过X射线晶体结构分析和光谱数据对这些配合物进行了表征。它们是烯丙基取代反应的全活性催化剂。对烯丙基配合物，烯丙基取代基的过渡态和产物烯烃配合物的DFT计算提供了进一步的机理见解。