(4S)-4-benzyl-3-[2-[(2R)-4-methyl-1-phenylmethoxypent-4-en-2-yl]oxyacetyl]-1,3-oxazolidin-2-one | 748770-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-4-benzyl-3-[2-[(2R)-4-methyl-1-phenylmethoxypent-4-en-2-yl]oxyacetyl]-1,3-oxazolidin-2-one
• CAS: 748770-51-6
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: TZAWJKSRIRAFIB-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙烯醛 、 (4S)-4-benzyl-3-[2-[(2R)-4-methyl-1-phenylmethoxypent-4-en-2-yl]oxyacetyl]-1,3-oxazolidin-2-one 在 N-甲基吡咯烷酮 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(S)-4-Benzyl-3-[2-((R)-1-benzyloxymethyl-3-methyl-but-3-enyloxy)-3-hydroxy-pent-4-enoyl]-oxazolidin-2-one
  参考文献：
  名称：

  An Improved Procedure for Asymmetric Aldol Additions withN-Acyl Oxazolidinones, Oxazolidinethiones and Thiazolidinethiones

  摘要：

  不对称的醛醇加成反应，使用N-酰基噁唑烷啉酮、噁唑烷硫酮和噻唑烷硫酮的氯钛烯醇盐，在反应中加入1当量的四氯化钛、1当量的二异丙基乙胺和1当量的N-甲基-2-吡咯烷酮，能够以高的非对映选择性得到“Evans syn”产物。使用N-丙酰基噁唑烷啉酮、噁唑烷硫酮和噻唑烷硫酮在0 °C下与化学计量量的醛反应，通常获得的选择性为94:6到>98:2。使用该方法，乙二醇酰亚胺同样获得了高选择性和高产率。

  DOI：

  10.1055/s-2004-825626
• 作为产物：
  描述：

  、 (S)-4-benzyl-2-oxazolidinone lithium salt 生成 (4S)-4-benzyl-3-[2-[(2R)-4-methyl-1-phenylmethoxypent-4-en-2-yl]oxyacetyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

  摘要：

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

  DOI：

  10.1021/jo0712695

文献信息

• An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12
  作者：Michael T. Crimmins、J. Michael Ellis

  DOI：10.1021/jo0712695

  日期：2008.3.1

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.
• An Improved Procedure for Asymmetric Aldol Additions with<i>N</i>-Acyl Oxazolidinones, Oxazolidinethiones and Thiazolidinethiones
  作者：Michael T. Crimmins、Jin She

  DOI：10.1055/s-2004-825626

  日期：——

  Asymmetric aldol additions using chlorotitanium enolates of N-acyl oxazolidinones, oxazolidinethiones and thiazoli­dinethiones proceed with high diastereoselectivity for the ‘Evans syn’ product using one equivalent of titanium tetrachloride, one equivalent of diisopropylethylamine and one equivalent of N-methyl-2-pyrrolidinone. Typical selectivities of 94:6 to >98:2 were obtained using N-propionyl oxazolidinones, oxazolidinethiones and thiazolidinethiones at 0 °C with stoichiometric amounts of aldehyde. Glycolate imides also gave high selectivities and high yields using this procedure.

  不对称的醛醇加成反应，使用N-酰基噁唑烷啉酮、噁唑烷硫酮和噻唑烷硫酮的氯钛烯醇盐，在反应中加入1当量的四氯化钛、1当量的二异丙基乙胺和1当量的N-甲基-2-吡咯烷酮，能够以高的非对映选择性得到“Evans syn”产物。使用N-丙酰基噁唑烷啉酮、噁唑烷硫酮和噻唑烷硫酮在0 °C下与化学计量量的醛反应，通常获得的选择性为94:6到>98:2。使用该方法，乙二醇酰亚胺同样获得了高选择性和高产率。