1,3-di(tert-butoxycarbonyl)succinimide | 1109280-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,3-di(tert-butoxycarbonyl)succinimide
• 英文别名: Ditert-butyl 2,5-dioxopyrrolidine-1,3-dicarboxylate
• CAS: 1109280-48-9
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: IDPLPJYATFRJSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-di(tert-butoxycarbonyl)succinimide 、 偶氮二甲酸二叔丁酯 在 dipotassium hydrogenphosphate 、 (11bS)-4,4-二丁基-4,5-二氢-2,6-双[3,5-双(三氟甲基)苯基]-3H-二萘并[2,1-c:1′,2′-e]溴化膦 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以99%的产率得到
  参考文献：
  名称：

  双萘基改性的季phospho盐作为手性相转移催化剂：β-酮酯的不对称胺化。

  摘要：

  DOI：

  10.1002/anie.200804140
• 作为产物：
  描述：

  N-trimethylsilylsuccinimide 、 二碳酸二叔丁酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以14%的产率得到1,3-di(tert-butoxycarbonyl)succinimide
  参考文献：
  名称：

  Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters

  摘要：

  Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochemistry of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/pi interactions that cumulatively account for the unusual stereoselectivity.

  DOI：

  10.1021/jo1002906

文献信息

• Highly efficient asymmetric amination of β-keto esters catalyzed by chiral quaternary ammonium bromides
  作者：Quan Lan、Xisheng Wang、Rongjun He、Changhua Ding、Keiji Maruoka

  DOI：10.1016/j.tetlet.2009.02.041

  日期：2009.7

  A highly efficient asymmetric amination of β-keto esters was achieved under phase transfer conditions using chiral quaternary ammonium bromide as a catalyst. The amination products were obtained in quantitative yields with up to 97% ee. One of the amination products represents a key intermediate for the preparation of aldose reductase inhibitor AS-3201.

  使用手性季铵溴化物作为催化剂，在相转移条件下实现了β-酮酯的高效不对称胺化。胺化产物的定量收率高达ee达97％。一种胺化产物代表用于制备醛糖还原酶抑制剂AS-3201的关键中间体。
• Binaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase Transfer Catalysts: Application to Asymmetric Amination of β-Keto Esters
  作者：Keiji Maruoka、Rongjun He

  DOI：10.1055/s-0029-1216848

  日期：2009.7

  A chiral quaternary tetraalkylphosphonium salt has been successfully utilized for the first time as a phase-transfer catalyst for asymmetric amination of β-keto esters in high yield with high ee. Asymmetric amination of a cyclic five-membered β-keto ester is a valuable method for preparing a key intermediate for asymmetric synthesis of aldose reductase inhibitor AS-3201 (Ranirestat). amination - asymmetric

  手性季四烷基phosph盐已成功地首次用作相转移催化剂，用于以高收率和高ee高收率地生产β-酮基酯。环状五元β-酮酯的不对称胺化是制备醛糖还原酶抑制剂AS-3201（Ranirestat）不对称合成的关键中间体的有价值的方法。 胺化-不对称合成-相转移催化-salts盐
• Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters
  作者：Alexander M. R. Smith、Henry S. Rzepa、Andrew J. P. White、Denis Billen、King Kuok (Mimi) Hii

  DOI：10.1021/jo1002906

  日期：2010.5.7

  Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochemistry of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/pi interactions that cumulatively account for the unusual stereoselectivity.
• Binaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase-Transfer Catalysts: Asymmetric Amination of β-Keto Esters
  作者：Rongjun He、Xisheng Wang、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1002/anie.200804140

  日期：2008.11.24