(E)-2-(phenylsulfonyl)-1,3-decadiene | 134005-49-5

• 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)-2-(phenylsulfonyl)-1,3-decadiene
• 英文别名: [(3E)-deca-1,3-dien-2-yl]sulfonylbenzene
• CAS: 134005-49-5
• 化学式: C₁₆H₂₂O₂S
• 分子量: 278.415
• InChiKey: FXJQEILJIZUIRS-FMIVXFBMSA-N

物化性质

• 沸点：
  426.9±18.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(phenylsulfonyl)-1,3-decadiene 在 氯化亚砜 、 15-冠醚-5 、 硫酸 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 N-isobutyl-3-(phenylsulfonyl)-4(E)-undecenamide
  参考文献：
  名称：

  Synthesis of 2(E),4(E)-dienamides and 2(E),4(E)-dienoates from 1,3-dienes via 2-phenylsulfonyl 1,3-dienes

  摘要：

  A procedure for the preparation of 2E,4E unsaturated carboxylic acid derivatives from dienes was developed. Transformation of terminal 1,3-dienes to (E)-2-phenylsulfonyl 1,3-dienes and subsequent addition of a carboxy anion equivalent and elimination of benzenesulfinic acid led to 2,4-dienoic amides and esters. In this way the natural products N-isobutyl-2(E)4,(E)-undecadienamide (1a), N-isobutyl-2(E),4(E)-decadienamide (pellitorine, 1b), and methyl 2(E),4(E)-decadienoate (1c) were obtained in high isomeric purity.

  DOI：

  10.1021/jo00014a034
• 作为产物：
  描述：

  phenylselenyl benzenesulfonate 、 (E)-1,3-decadiene 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 生成 (E)-2-(phenylsulfonyl)-1,3-decadiene
  参考文献：
  名称：

  Synthesis of 2(E),4(E)-dienamides and 2(E),4(E)-dienoates from 1,3-dienes via 2-phenylsulfonyl 1,3-dienes

  摘要：

  A procedure for the preparation of 2E,4E unsaturated carboxylic acid derivatives from dienes was developed. Transformation of terminal 1,3-dienes to (E)-2-phenylsulfonyl 1,3-dienes and subsequent addition of a carboxy anion equivalent and elimination of benzenesulfinic acid led to 2,4-dienoic amides and esters. In this way the natural products N-isobutyl-2(E)4,(E)-undecadienamide (1a), N-isobutyl-2(E),4(E)-decadienamide (pellitorine, 1b), and methyl 2(E),4(E)-decadienoate (1c) were obtained in high isomeric purity.

  DOI：

  10.1021/jo00014a034

文献信息

• Synthesis of 2(E),4(E)-dienamides and 2(E),4(E)-dienoates from 1,3-dienes via 2-phenylsulfonyl 1,3-dienes
  作者：Niklas A. Plobeck、Jan E. Baeckvall

  DOI：10.1021/jo00014a034

  日期：1991.7

  A procedure for the preparation of 2E,4E unsaturated carboxylic acid derivatives from dienes was developed. Transformation of terminal 1,3-dienes to (E)-2-phenylsulfonyl 1,3-dienes and subsequent addition of a carboxy anion equivalent and elimination of benzenesulfinic acid led to 2,4-dienoic amides and esters. In this way the natural products N-isobutyl-2(E)4,(E)-undecadienamide (1a), N-isobutyl-2(E),4(E)-decadienamide (pellitorine, 1b), and methyl 2(E),4(E)-decadienoate (1c) were obtained in high isomeric purity.