[(3R,4S)-4-phenylmethoxyhexa-1,5-dien-3-yl] but-3-enoate | 1203559-98-1

• 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: [(3R,4S)-4-phenylmethoxyhexa-1,5-dien-3-yl] but-3-enoate
• CAS: 1203559-98-1
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: WAOMUUPMQUMVNF-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3R,4S)-4-phenylmethoxyhexa-1,5-dien-3-yl] but-3-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2R)-2-[(1S)-1-phenylmethoxyprop-2-enyl]-2,5-dihydropyran-6-one
  参考文献：
  名称：

  Facile synthesis of (−)-6-acetoxy-5-hexadecanolide by size-selective ring-closing/cross metathesis

  摘要：

  A total synthesis of (-)-6-acetoxy-5-hexadecanolide, in six steps and 37% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. The key synthetic step is a size-selective ring-closing/cross metathesis reaction in which lactone formation and alkyl chain extension are accomplished in an efficient one-pot process. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.179
• 作为产物：
  描述：

  乙烯基乙酸 、 (3R,4S)-4-phenylmethoxyhexa-1,5-dien-3-ol 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到[(3R,4S)-4-phenylmethoxyhexa-1,5-dien-3-yl] but-3-enoate
  参考文献：
  名称：

  Facile synthesis of (−)-6-acetoxy-5-hexadecanolide by size-selective ring-closing/cross metathesis

  摘要：

  A total synthesis of (-)-6-acetoxy-5-hexadecanolide, in six steps and 37% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. The key synthetic step is a size-selective ring-closing/cross metathesis reaction in which lactone formation and alkyl chain extension are accomplished in an efficient one-pot process. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.179

文献信息

• Facile synthesis of (−)-6-acetoxy-5-hexadecanolide by size-selective ring-closing/cross metathesis
  作者：Kevin J. Quinn、John M. Curto、Kevin P. McGrath、Neal A. Biddick

  DOI：10.1016/j.tetlet.2009.09.179

  日期：2009.12

  A total synthesis of (-)-6-acetoxy-5-hexadecanolide, in six steps and 37% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. The key synthetic step is a size-selective ring-closing/cross metathesis reaction in which lactone formation and alkyl chain extension are accomplished in an efficient one-pot process. (c) 2009 Elsevier Ltd. All rights reserved.