N-(tert-butoxycarbonyl)-phthalimide | 150220-29-4

• 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: N-(tert-butoxycarbonyl)-phthalimide
• 英文别名: Tert-butyl 1,3-dioxoisoindole-2-carboxylate
• CAS: 150220-29-4
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: IXJWAXMNZUFWIH-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  362.4±25.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(tert-butoxycarbonyl)-phthalimide 在 羟胺 作用下， 以 乙腈 为溶剂， 以95%的产率得到N-羟基邻苯二甲酰亚胺
  参考文献：
  名称：

  MILD AND CONVENIENT ONE POT SYNTHESIS OFN-HYDROXYIMIDES FROMN-UNSUBSTITUTED IMIDES

  摘要：

  A new, one pot synthesis of various N-hydroxyimides from N-unsubstituted imides is described. Imides are first transformed into their N-Boc derivatives, which are next reacted with aqueous hydroxylamine, providing crystalline hydroxylammonium salts of the corresponding N-hydroxyimides. Filtration and acidic workup affords pure N-hydroxyimides.

  DOI：

  10.1081/scc-100103264
• 作为产物：
  描述：

  二碳酸二叔丁酯 以 正己烷 、 苯 为溶剂， 反应 8.0h， 生成 N-(tert-butoxycarbonyl)-phthalimide
  参考文献：
  名称：

  一种新型的叔丁氧基羰基化试剂：1-叔丁氧基-2-叔丁氧基羰基1,2-二氢异喹啉（BBDI）

  摘要：

  1-叔丁氧基-2-叔丁氧基羰基-1,2-二氢异喹啉（BBDI）作为叔丁氧基羰基化试剂用于酸性质子质底物（例如苯酚，芳族和脂肪族胺盐酸盐以及芳香族羧酸）的用途描述了不存在碱的情况。在温和条件下，该反应以高产率进行化学选择。

  DOI：

  10.1016/j.tet.2006.09.063

文献信息

• Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tert-butyl ethers from alcohols
  作者：F. Shirini、M. A. Zolfigol、M. Abedini

  DOI：10.1007/bf03246047

  日期：2010.9

  (SaSA), as a stable reagent is easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This compound is able to catalyze conversion of amines to their corresponding N-Boc protected amines with (Boc)2O. Alcohols were also converted to their corresponding tert-butyl ethers. All reactions took place under mild conditions giving the desired products in good to high

  通过在室温下使糖精与纯净的氯磺酸反应，可以容易地制备作为稳定试剂的糖精磺酸（SaSA）。该化合物能够用（Boc）2 O催化胺转化为其相应的N- Boc保护的胺。醇也被转化为其相应的叔丁基醚。所有反应均在温和条件下进行，以高至高收率得到所需产物。
• Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
  作者：Tetsuya Sengoku、Ayako Miyoshi、Tamaki Tsuda、Toshiyasu Inuzuka、Masami Sakamoto、Masaki Takahashi、Hidemi Yoda

  DOI：10.1016/j.tet.2020.131252

  日期：2020.6

  Catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds is developed. Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities

  开发了基于亚甲基内酰胺的N，O-螺环化合物的催化对映选择性形成。由N-羰基邻苯二甲酰亚胺和β-氨基官能化的烯丙基硼酸酯制备的羟基内酰胺在催化量的MgBr 2和手性氨基苯酚存在下进行开环-不对称重合反应，从而以优异的收率和高对映选择性提供相应的N，O-螺环化合物。
• Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of <i>N</i> -Carbonyl Imides
  作者：Tetsuya Sengoku、Yuta Kamiya、Ai Kawakami、Masaki Takahashi、Hidemi Yoda

  DOI：10.1002/ejoc.201701112

  日期：2017.11.2

  This communication describes the utility of β-amido allylboronate as a nucleophile in the catalytic amide allylation of N-carbonyl imides. The reaction of the imide substrates with the boronates has been accomplished by using catalytic zinc bromide and basic additives (ethanol, potassium carbonate and 18-crown 6-ether), affording azaspiro-γ-lactones through a ring opening-reclosure process with yields

  本通讯描述了 β-酰氨基烯丙基硼酸酯在 N-羰基酰亚胺的催化酰胺烯丙基化中作为亲核试剂的用途。通过使用催化溴化锌和碱性添加剂（乙醇、碳酸钾和 18-冠 6-醚）完成酰亚胺底物与硼酸盐的反应，通过开环-重闭过程得到氮杂螺-γ-内酯，产率提高到 100%。这里建立的具有成本效益且易于操作的方法可用于克级合成，而不会显着降低反应效率。
• Piperazine- and piperidine-derivatives as melanocortin receptor agonists
  申请人：——

  公开号：US20040082590A1

  公开（公告）日：2004-04-29

  The present invention relates to melanocortin receptor agonists of formula I, which is useful in the treatment of obesity, diabetes and male and/or female sexual dysfunction. 1

  本发明涉及公式I的黑素皮质素受体激动剂，可用于治疗肥胖症、糖尿病以及男性和/或女性性功能障碍。
• Pd-Catalyzed Asymmetric Dearomatization of Indoles via Decarbonylative Heck-Type Reaction of Thioesters
  作者：Ming-Liang Han、Wei Huang、Yu-Wen Liu、Min Liu、Hui Xu、Hai Xiong、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.0c03897

  日期：2021.1.1

  We report herein a palladium-catalyzed ligand-promoted asymmetric dearomatization of indoles via the decarbonylation of thioesters and the subsequent reductive Heck reaction. This protocol provides a facile and efficient way to construct an aza-quaternary stereocenter at the C2 position of indolines. A variety of functional groups and substitutions could be well tolerated, affording the substituted

  我们在本文中报道了通过硫酯的脱羰作用和随后的还原性Heck反应，钯催化的配体促进的吲哚的不对称脱芳香化作用。该协议为在二氢吲哚的C2位置构建氮杂四元立体中心提供了一种简便而有效的方法。可以很好地耐受各种官能团和取代基，从而提供具有高对映选择性的取代二氢吲哚。