methyl 6-hydroxy-4-methylenehexanoate | 160189-63-9

• 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 6-hydroxy-4-methylenehexanoate
• 英文别名: Methyl 6-hydroxy-4-methylidenehexanoate；methyl 6-hydroxy-4-methylidenehexanoate
• CAS: 160189-63-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: DXFJDHCNKBFSJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxy-4-methylenehexanoate 在 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 lithium aluminium tetrahydride 、 sodium amalgam 、 三丁基膦 、 二苯基二硒醚 、 四丁基氟化铵 、 双氧水 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 生成 (E)-7-[(4S,5R)-5-[(2S)-butan-2-yl]-4-methoxycarbonyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylidenehept-6-enoic acid
  参考文献：
  名称：

  Total synthesis of alternaric acid

  摘要：

  A total synthesis of alternaric acid (1) has been achieved. Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enolacyl group of beta-keto-delta-valerolactone toward alpha-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1.

  DOI：

  10.1016/s0040-4039(00)77605-2
• 作为产物：
  描述：

  衣康酸二甲酯 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 水 、 sodium hydride 、 对甲苯磺酸 、 1,2-双(二苯基膦)乙烷 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二甲基亚砜 、 苯 为溶剂， 反应 49.0h， 生成 methyl 6-hydroxy-4-methylenehexanoate
  参考文献：
  名称：

  Total Synthesis and Stereochemistry of Alternaric Acid

  摘要：

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

  DOI：

  10.1021/jo00096a016

文献信息

• Total synthesis of alternaric acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1016/s0040-4039(00)77605-2

  日期：1993.4

  A total synthesis of alternaric acid (1) has been achieved. Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enolacyl group of beta-keto-delta-valerolactone toward alpha-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1.
• Total Synthesis and Stereochemistry of Alternaric Acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1021/jo00096a016

  日期：1994.8

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.