ethyl 2-hydroxypyrrolidine-1-carboxylate | 69352-25-6

• 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: ethyl 2-hydroxypyrrolidine-1-carboxylate
• 英文别名: 2-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester
• CAS: 69352-25-6
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: XAMJXXZGENRCHA-UHFFFAOYSA-N

物化性质

• 沸点：
  256.6±33.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxypyrrolidine-1-carboxylate 以 甲苯 为溶剂， 反应 36.0h， 生成 2-吡咯啉-1-乙酸苄酯
  参考文献：
  名称：

  Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer–Villiger biocatalyst reveals novel regiodivergent oxidations

  摘要：

  Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.003
• 作为产物：
  描述：

  ethyl 2-oxopyrrolidine-1-carboxylate 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到ethyl 2-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  四元，五元，六元和七元N-烷氧基羰基内酰胺加氢锆化成内酰胺

  摘要：

  据报道，一般，实用和有效地将四，五，六和七元的N-烷氧基羰基内酰胺还原为醛氧化态。还原方法包括在温和的条件下通过Cp 2 Zr（H）Cl进行加氢锆化反应，并且反应时间非常短，并且收率极好。用Schwartz试剂对N-烷氧基羰基内酰胺进行加氢锆化反应是形成具有高官能团耐受性的内酰胺的最温和，最通用的方法。

  DOI：

  10.1016/j.tetlet.2011.10.006

文献信息

• Introduction of Functional Groups into the a-Position of N-Alkoxycarbonylpyrrolidines
  作者：Tatsuo Nagasaka、Hirohisa Tamano、Tomoaki Maekawa、Fumiko Hamaguchi

  DOI：10.3987/r-1987-03-0617

  日期：——
• NAGASAKA, TATSUO;YAMAMOTO, HIROTO;HAYAGHI, HIDEKI;WATANABE, MARIKO;HAMAGU+, HETEROCYCLES., 29,(1989) N, C. 155-164
  作者：NAGASAKA, TATSUO、YAMAMOTO, HIROTO、HAYAGHI, HIDEKI、WATANABE, MARIKO、HAMAGU+

  DOI：——

  日期：——
• NAGASAKA, TATSUO;TAMANO, HIROHISA;MAEKAWA, TOMOAKI;HAMAGUCHI, FUMIKO, HETEROCYCLES, 26,(1987) N 3, 617-624
  作者：NAGASAKA, TATSUO、TAMANO, HIROHISA、MAEKAWA, TOMOAKI、HAMAGUCHI, FUMIKO

  DOI：——

  日期：——
• Hydrozirconation of four-, five-, six- and seven-membered N-alkoxycarbonyl lactams to lactamols
  作者：Anna Piperno、Caterina Carnovale、Salvatore V. Giofrè、Daniela Iannazzo

  DOI：10.1016/j.tetlet.2011.10.006

  日期：2011.12

  practical, and efficient reduction of four-, five-, six- and, seven-membered N-alkoxycarbonyl lactams to the aldehyde oxidation state is reported. The reduction methodology involves the hydrozirconation reaction by Cp2Zr(H)Cl under mild conditions and proceeds with very short reaction times and in excellent to good yields. The hydrozirconation of N-alkoxycarbonyl lactams with the Schwartz reagent demonstrated

  据报道，一般，实用和有效地将四，五，六和七元的N-烷氧基羰基内酰胺还原为醛氧化态。还原方法包括在温和的条件下通过Cp 2 Zr（H）Cl进行加氢锆化反应，并且反应时间非常短，并且收率极好。用Schwartz试剂对N-烷氧基羰基内酰胺进行加氢锆化反应是形成具有高官能团耐受性的内酰胺的最温和，最通用的方法。
• Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer–Villiger biocatalyst reveals novel regiodivergent oxidations
  作者：Michael J. Fink、Thomas C. Fischer、Florian Rudroff、Hanna Dudek、Marco W. Fraaije、Marko D. Mihovilovic

  DOI：10.1016/j.molcatb.2011.07.003

  日期：2011.12

  Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids. (C) 2011 Elsevier B.V. All rights reserved.