(2S,5S)-2-tert-butyl-5-ethoxycarbonylethyl-5-methyl-1,3-dioxolan-4-one | 146275-06-1

• 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: (2S,5S)-2-tert-butyl-5-ethoxycarbonylethyl-5-methyl-1,3-dioxolan-4-one
• 英文别名: ethyl 3-[(2S,4R)-2-tert-butyl-4-methyl-5-oxo-1,3-dioxolan-4-yl]propanoate
• CAS: 146275-06-1
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: DUTUATLQLNBZDO-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-tert-butyl-5-ethoxycarbonylethyl-5-methyl-1,3-dioxolan-4-one 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (5R)-γ-valerolactone γ-carboxylic acid
  参考文献：
  名称：

  使用手性1,3-二氧戊环-4-酮的不对称自由基加成

  摘要：

  在手性（c，d）烯烃（2 S）-2-叔丁基-5-乙氧基羰基亚甲基-1,3-二氧戊环-4-酮1上添加烷基后，观察到适度的面部选择性。随后从三丁基锡烷提取氢的过程具有出色的不对称立体控制，从而导致四种可能的非对映异构体中的两个具有高非对映异构体过量度。由（2 R，5 R）-5-烷基-5-溴-1,3-二氧戊环-4-酮获得的手性基团向丙烯酸乙酯的加成表现出高度的不对称1,3-诱导作用。

  DOI：

  10.1016/s0040-4039(00)74714-9
• 作为产物：
  描述：

  (2RS,5RS)-5-bromo-2-(1,1-dimethylethyl)-5-methyl-1,3-dioxolane-4-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 丙烯酸乙酯 作用下， 以 苯 为溶剂， 以55%的产率得到(2S,5S)-2-tert-butyl-5-ethoxycarbonylethyl-5-methyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Stereoselective Radical Additions using chiral 1,3-dioxolanones derived from lactic and malic acid

  摘要：

  The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.

  DOI：

  10.1002/prac.19953370126

文献信息

• Asymmetric radical additions using chiral 1,3-dioxolane-4-ones
  作者：Georg Kneer、Jochen Mattay

  DOI：10.1016/s0040-4039(00)74714-9

  日期：1992.12

  selectivities are observed in additions of alkyl radicals to the chiral (c,d) olefin (2S)-2-tert-butyl-5-ethoxycarbonylmethylene-1,3-dioxolane-4-one1. The following hydrogen abstraction from tributylstannane proceeds with excellent asymmetric stereocontrol, leading to two of four possible diastereoisomers with high diastereomeric excesses. Additions of chiral radicals obtained from (2R,5R)-5-alkyl-5-bromo-1

  在手性（c，d）烯烃（2 S）-2-叔丁基-5-乙氧基羰基亚甲基-1,3-二氧戊环-4-酮1上添加烷基后，观察到适度的面部选择性。随后从三丁基锡烷提取氢的过程具有出色的不对称立体控制，从而导致四种可能的非对映异构体中的两个具有高非对映异构体过量度。由（2 R，5 R）-5-烷基-5-溴-1,3-二氧戊环-4-酮获得的手性基团向丙烯酸乙酯的加成表现出高度的不对称1,3-诱导作用。
• Stereoselective Radical Additions using chiral 1,3-dioxolanones derived from lactic and malic acid
  作者：Georg Kneer、Jochen Mattay、Andreas Heidbreder、Gerhard Raabe、Bernt Krebs、Mechtild L�ge

  DOI：10.1002/prac.19953370126

  日期：——

  The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.