(E)-5-[2-[(2S)-2-hydroxy-3-phenylmethoxypropyl]-1,3-dithian-2-yl]pent-2-enal | 1598426-84-6

• 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: (E)-5-[2-[(2S)-2-hydroxy-3-phenylmethoxypropyl]-1,3-dithian-2-yl]pent-2-enal
• CAS: 1598426-84-6
• 化学式: C₁₉H₂₆O₃S₂
• 分子量: 366.546
• InChiKey: DTQDQBMLPUEPTN-VBAWXRRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-5-[2-[(2S)-2-hydroxy-3-phenylmethoxypropyl]-1,3-dithian-2-yl]pent-2-enal 在 sodium tetrahydroborate 、 (2R)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 苯甲酸 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 24.5h， 生成 (2S)-2-anilinooxy-2-[(9S,11S)-11-(phenylmethoxymethyl)-10-oxa-1,5-dithiaspiro[5.6]dodecan-9-yl]ethanol
  参考文献：
  名称：

  Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction

  摘要：

  Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided alpha,alpha'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/alpha-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.

  DOI：

  10.1021/ol500773w
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以74%的产率得到(E)-5-[2-[(2S)-2-hydroxy-3-phenylmethoxypropyl]-1,3-dithian-2-yl]pent-2-enal
  参考文献：
  名称：

  Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction

  摘要：

  Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided alpha,alpha'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/alpha-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.

  DOI：

  10.1021/ol500773w