(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxane-4-carbaldehyde | 1147106-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxane-4-carbaldehyde
• CAS: 1147106-99-7
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: FLXSPFMNQJFPCH-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (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
• 作为产物：
  描述：

  [(2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxan-4-yl]methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R,4S,6S)-6-ethynyl-6-methyl-2-phenyl-1,3-dioxane-4-carbaldehyde
  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.