(R)-3-ethoxycarbonyl-1-thia-4-azaspiro[4.5]decane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-ethoxycarbonyl-1-thia-4-azaspiro[4.5]decane
• 英文别名: (R)-1-thia-4-aza-spiro[4.5]decane-3-carboxylic acid ethyl ester；(R)-1-Thia-4-aza-spiro[4.5]decan-3-carbonsaeure-aethylester；ethyl (3R)-1-thia-4-azaspiro[4.5]decane-3-carboxylate
• 化学式: C₁₁H₁₉NO₂S
• 分子量: 229.343
• InChiKey: DHNKRUBKZXCRCF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-ethoxycarbonyl-1-thia-4-azaspiro[4.5]decane 、 苯基溴化镁 以 乙醚 为溶剂， 反应 2.0h， 生成 (R)-diphenyl-2-(1-thia-4-aza-spiro[4.5]decan-3-yl)-methanol
  参考文献：
  名称：

  Sulfur-containing β-amino alcohols as catalysts in enantioselective synthesis

  摘要：

  Oxazaborolidine catalysts generated in situ from cyclic or acyclic sulfur containing (R)-cysteine, (S)-penicillamine and (S)-methionine derivates and BH3 have been applied successfully to the enantiocontrolled, catalytic reduction of aromatic ketones. The corresponding sec alcohols could be obtained in excellent enantiomeric excess, up to 100% ee. Using these chiral auxiliaries in the enantioselective addition of diethylzinc to aldehydes afforded optically active sec alcohols in enantiomeric excess up to 93% ee. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00193-6
• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 环己酮 生成 (R)-3-ethoxycarbonyl-1-thia-4-azaspiro[4.5]decane
  参考文献：
  名称：

  螺（类固醇）噻唑烷。

  摘要：

  DOI：

  10.1021/ja01189a077

文献信息

• Novel thiazolidine derivatives as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
  作者：Qinglin Meng、Yuelan Li、Yan He、Yedi Guan

  DOI：10.1016/s0957-4166(00)00391-8

  日期：2000.11

  New chiral thiazolidine derivatives were synthesized conveniently from natural l-cysteine and showed good enantioselectivity (up to 90% ee) in the addition of diethylzinc to aldehydes. The catalytic efficiency of the thiazolidine derivatives is influenced by the different structures of the thiazolidine rings and the bulkiness of R moiety in the ester groups.

  新的手性噻唑烷衍生物可方便地从天然L-半胱氨酸合成，并且在将二乙基锌添加到醛中后显示出良好的对映选择性（最高90％ee）。噻唑烷衍生物的催化效率受噻唑烷环的不同结构和酯基团中R部分的体积的影响。
• Sulfur-containing β-amino alcohols as catalysts in enantioselective synthesis
  作者：Wilhelm Trentmann、Thomas Mehler、Jürgen Martens

  DOI：10.1016/s0957-4166(97)00193-6

  日期：1997.6

  Oxazaborolidine catalysts generated in situ from cyclic or acyclic sulfur containing (R)-cysteine, (S)-penicillamine and (S)-methionine derivates and BH3 have been applied successfully to the enantiocontrolled, catalytic reduction of aromatic ketones. The corresponding sec alcohols could be obtained in excellent enantiomeric excess, up to 100% ee. Using these chiral auxiliaries in the enantioselective addition of diethylzinc to aldehydes afforded optically active sec alcohols in enantiomeric excess up to 93% ee. (C) 1997 Elsevier Science Ltd.
• Spiro (Steroid) Thiazolidines¹
  作者：Seymour Lieberman、Paul Brazeau、Lucie B. Hariton

  DOI：10.1021/ja01189a077

  日期：1948.9