di-tert-butyl 2-(2-oxoethyl)malonate | 62631-26-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: di-tert-butyl 2-(2-oxoethyl)malonate
• 英文别名: Di-t-butyl-(formylmethyl)malonat；Di-tert-butyl (2-oxoethyl)propanedioate；ditert-butyl 2-(2-oxoethyl)propanedioate
• CAS: 62631-26-9
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: MFFMQCQLPKINPU-UHFFFAOYSA-N

物化性质

• 沸点：
  321.9±32.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 2-(2-oxoethyl)malonate 在 palladium on activated charcoal 氢气 、 双氧水 作用下， 以 乙醇 、 异丙醇 为溶剂， 生成 L-(+)-γ-Carboxyglutaminsaeure-1-amid-γ,γ'-di-t-butylester
  参考文献：
  名称：

  Asymmetrische Synthese vonL-?-Carboxyglutamins�ure-Derivaten

  摘要：

  Asymmetric synthesis of L‐γ‐carboxyglutamic acid derivativesA modified Strecker synthesis according to Patel & Worsley was used to prepare γ,γ′‐di‐t‐butyl L(−)‐N‐phthaloyl‐γ‐carboxyglutamate with almost 100% optical purity and an overall yield of about 10% relative to di‐t‐butyl malonate, or 20% relative to (−)‐α‐methyl‐benzylamine (s. Scheme).

  DOI：

  10.1002/hlca.19770600107
• 作为产物：
  描述：

  tert-butyl 2-(tert-butyloxycarbonyl)-4-pentenoate 生成 di-tert-butyl 2-(2-oxoethyl)malonate
  参考文献：
  名称：

  Asymmetrische Synthese vonL-?-Carboxyglutamins�ure-Derivaten

  摘要：

  Asymmetric synthesis of L‐γ‐carboxyglutamic acid derivativesA modified Strecker synthesis according to Patel & Worsley was used to prepare γ,γ′‐di‐t‐butyl L(−)‐N‐phthaloyl‐γ‐carboxyglutamate with almost 100% optical purity and an overall yield of about 10% relative to di‐t‐butyl malonate, or 20% relative to (−)‐α‐methyl‐benzylamine (s. Scheme).

  DOI：

  10.1002/hlca.19770600107

文献信息

• Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates
  作者：Zhengbo Zhu、Hemant S. Chandak、Daniel Seidel

  DOI：10.1021/acs.orglett.8b01642

  日期：2018.7.6

  Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-(2-oxoethyl)malonates in the presence of catalytic amounts of benzoic acid. These reactions install a fully saturated five-membered ring and provide access to structures closely related to the natural products crispine A and harmicine.

  胺（例如 1,2,3,4-四氢异喹啉）在催化量的苯甲酸存在下与 2-(2-氧代乙基)丙二酸酯发生氧化还原中性环化。这些反应安装了完全饱和的五元环，并提供了与天然产物 Crispine A 和 Harmicine 密切相关的结构。
• Asymmetrische Synthese vonL-?-Carboxyglutamins�ure-Derivaten
  作者：Max Oppliger、Robert Schwyzer

  DOI：10.1002/hlca.19770600107

  日期：1977.1.26

  Asymmetric synthesis of L‐γ‐carboxyglutamic acid derivativesA modified Strecker synthesis according to Patel & Worsley was used to prepare γ,γ′‐di‐t‐butyl L(−)‐N‐phthaloyl‐γ‐carboxyglutamate with almost 100% optical purity and an overall yield of about 10% relative to di‐t‐butyl malonate, or 20% relative to (−)‐α‐methyl‐benzylamine (s. Scheme).