(S)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-3-(1-oxo-but-2-enyl)-oxazolidin-2-one | 171755-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-3-(1-oxo-but-2-enyl)-oxazolidin-2-one
• 英文别名: (4S)-3-[(E)-but-2-enoyl]-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-1,3-oxazolidin-2-one
• CAS: 171755-45-6
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: VGFJWHAEXKTLQX-SZTZYQKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-3-(1-oxo-but-2-enyl)-oxazolidin-2-one 在 bis(isopropyloxy)chloroborane 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (S)-3-((S)-3-Chloro-butyryl)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-oxazolidin-2-one 、 (S)-3-((R)-3-Chloro-butyryl)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-oxazolidin-2-one
  参考文献：
  名称：

  Conjugate addition of chloride to α,β-unsaturated chiral imides promoted by BCl3-derivatives. Part II

  摘要：

  The diastereoselective hydrochlorination of alpha,beta-unsaturated chiral imides by reaction with BCl(2)OR or BCl(OR)(2) type reagents is described. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-tryptophan. An hypothesis on the donor-acceptor interactions, between the substrate and the Lewis acids, that drive the attack of the chloride preferentially to one face of the alkenoyl chain is reported.

  DOI：

  10.1016/0957-4166(95)00255-n
• 作为产物：
  描述：

  N-[叔丁氧羰基]-L-色氨酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 (S)-4-(1H-indol-3-ylmethyl)-5,5-dimethyl-3-(1-oxo-but-2-enyl)-oxazolidin-2-one
  参考文献：
  名称：

  （S）-色氨酸衍生的新型手性助剂的合成

  摘要：

  通过受保护的氨基酸3与各种格氏试剂的反应，描述了衍生自（S）-色氨酸的手性氨基醇4的合成。将氨基醇转化成相应的恶唑烷-2-酮2，并用2-丁烯酰氯和2-己烯酰氯酰化，得到酰亚胺5a-e。通过1 H NMR，NOEDIF实验和半经验AM1计算，对恶唑烷-2-酮2和迈克尔受体5进行构象分析。

  DOI：

  10.1016/0957-4166(95)00254-m

文献信息

• Synthesis of new chiral auxiliaries derived from (S)-tryptophan
  作者：Giuliana Cardillo、Luca Gentilucci、Claudia Tomasini、Laura Tomasoni

  DOI：10.1016/0957-4166(95)00254-m

  日期：1995.8

  The synthesis of chiral aminoalcohols 4 derived from (S)-tryptophan is described, by reaction of the protected amino acid 3 with various Grignard reagents. The aminoalcohols were transformed into the corresponding oxazolidin-2-ones 2 and acylated with 2-butenoyl chloride and 2-hexenoyl chloride, affording the imides 5a-e. The conformational analysis of both the oxazolidin-2-ones 2 and the Michael acceptors

  通过受保护的氨基酸3与各种格氏试剂的反应，描述了衍生自（S）-色氨酸的手性氨基醇4的合成。将氨基醇转化成相应的恶唑烷-2-酮2，并用2-丁烯酰氯和2-己烯酰氯酰化，得到酰亚胺5a-e。通过1 H NMR，NOEDIF实验和半经验AM1计算，对恶唑烷-2-酮2和迈克尔受体5进行构象分析。
• Conjugate addition of chloride to α,β-unsaturated chiral imides promoted by BCl3-derivatives. Part II
  作者：Giuliana Cardillo、Emanuela Di Martino、Luca Gentilucci、Claudia Tomasini、Laura Tomasoni

  DOI：10.1016/0957-4166(95)00255-n

  日期：1995.8

  The diastereoselective hydrochlorination of alpha,beta-unsaturated chiral imides by reaction with BCl(2)OR or BCl(OR)(2) type reagents is described. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-tryptophan. An hypothesis on the donor-acceptor interactions, between the substrate and the Lewis acids, that drive the attack of the chloride preferentially to one face of the alkenoyl chain is reported.