methyl (Z)-3-[(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]prop-2-enoate | 1147107-01-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-3-[(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]prop-2-enoate
• CAS: 1147107-01-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: ASHSRSKGRXXDKA-RHVVSHQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-[(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]prop-2-enoate 在 硫酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到(2S)-2-[(2S)-2-hydroxy-2-methylbut-3-ynyl]-2H-furan-5-one
  参考文献：
  名称：

  Stereocontrolled entry to the tricyclo[3.3.0]oxoheptane core of bielschowskysin by a [2+2] cycloaddition of an allene-butenolide

  摘要：

  As part of ongoing transannulation studies, the practical synthesis of an allene-linked gamma-butenolide from L-malic acid and its substrate-controlled [2+2] photocycloaddition to the tricyclic core of bielschowskysin (1) are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.131
• 作为产物：
  描述：

  (2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxane-4-carbaldehyde 、 甲氧甲酰基甲基三苯基溴化膦 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以60%的产率得到methyl (Z)-3-[(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]prop-2-enoate
  参考文献：
  名称：

  Stereocontrolled entry to the tricyclo[3.3.0]oxoheptane core of bielschowskysin by a [2+2] cycloaddition of an allene-butenolide

  摘要：

  As part of ongoing transannulation studies, the practical synthesis of an allene-linked gamma-butenolide from L-malic acid and its substrate-controlled [2+2] photocycloaddition to the tricyclic core of bielschowskysin (1) are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.131

文献信息

• Stereocontrolled entry to the tricyclo[3.3.0]oxoheptane core of bielschowskysin by a [2+2] cycloaddition of an allene-butenolide
  作者：Ru Miao、Subramanian G. Gramani、Martin J. Lear

  DOI：10.1016/j.tetlet.2009.01.131

  日期：2009.4

  As part of ongoing transannulation studies, the practical synthesis of an allene-linked gamma-butenolide from L-malic acid and its substrate-controlled [2+2] photocycloaddition to the tricyclic core of bielschowskysin (1) are described. (C) 2009 Elsevier Ltd. All rights reserved.