(1R)-1-[(2R,3R)-(3-phenyloxiran-2-yl)]but-3-enyl acrylate | 1174166-10-9

• 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: (1R)-1-[(2R,3R)-(3-phenyloxiran-2-yl)]but-3-enyl acrylate
• 英文别名: [(1R)-1-[(2R,3R)-3-phenyloxiran-2-yl]but-3-enyl] prop-2-enoate
• CAS: 1174166-10-9
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: WMYLKBFVAKGLTE-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(2R,3R)-(3-phenyloxiran-2-yl)]but-3-enyl acrylate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(6R,7R,8R)-(+)-goniothalamin oxide
  参考文献：
  名称：

  De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

  摘要：

  A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis was installed by means of a Krische or Leighton allylation. The remaining stereochemistry was installed by a diastereoselective epoxidation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.097
• 作为产物：
  描述：

  (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(1R)-1-[(2S,3S)-3-phenyloxiran-2-yl]but-3-en-1-yl acrylate
  参考文献：
  名称：

  De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

  摘要：

  A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis was installed by means of a Krische or Leighton allylation. The remaining stereochemistry was installed by a diastereoselective epoxidation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.097

文献信息

• De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations
  作者：Philip Harsh、George A. O'Doherty

  DOI：10.1016/j.tet.2009.03.097

  日期：2009.6

  A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis was installed by means of a Krische or Leighton allylation. The remaining stereochemistry was installed by a diastereoselective epoxidation. (C) 2009 Elsevier Ltd. All rights reserved.