[(2R,4S)-4-(3,5-dimethylphenoxy)pentan-2-yl] 2-diazoacetate | 404891-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2R,4S)-4-(3,5-dimethylphenoxy)pentan-2-yl] 2-diazoacetate
• CAS: 404891-66-3
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: WSHYNMVCPMABFH-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,4S)-4-(3,5-dimethylphenoxy)pentan-2-yl] 2-diazoacetate 在 咪唑 、 potassium fluoride 、 dirhodium tetraacetate 、 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.67h， 生成
  参考文献：
  名称：

  Stereoselective hydrogenation of conjugate diene directed by hydroxy group and asymmetric synthesis of deoxypolypropionate units

  摘要：

  Optically active cyclic compounds carrying a conjugate diene and two hydroxy groups were prepared through the intramolecular Buchner reaction with a chiral tether and succeeding stereoselective conversion. Hydrogenation of the diene in the first step was not regio-selective but resulted in three regioisomeric monoenes. Nevertheless. the final saturated product carrying two stereogenic centers could be obtained in 98% stereochemical purity on further hydrogenation under optimized conditions. The high stereoselectivity throughout the multiple pathways is attributable to the effective direction by the hydroxy group. Ring cleavage of the produced stereochemically pure seven-membered ring compounds successfully resulted in synthetic intermediates for deoxypolypropionates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.128
• 作为产物：
  描述：

  3,5-二甲基苯酚 在 对甲苯磺酰叠氮 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 42.0h， 生成 [(2R,4S)-4-(3,5-dimethylphenoxy)pentan-2-yl] 2-diazoacetate
  参考文献：
  名称：

  Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene

  摘要：

  Optically active polypropionate units were synthesized in 9-11 steps from 3,5-dimethylphenol. The sequence consists of the BUchner reaction controlled by a chiral 2,4-pentanediol tether and diastereoselective hydrogenation over Raney nickel.

  DOI：

  10.1021/ol0483596

文献信息

• Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene
  作者：Takashi Sugimura、Yasuhiro Sato、Chun Young Im、Tadashi Okuyama

  DOI：10.1021/ol0483596

  日期：2004.11.1

  Optically active polypropionate units were synthesized in 9-11 steps from 3,5-dimethylphenol. The sequence consists of the BUchner reaction controlled by a chiral 2,4-pentanediol tether and diastereoselective hydrogenation over Raney nickel.
• ——
  作者：Takashi Sugimura、Futoshi Nishida、Takahiro Tei、Akiko Morisawa、Akira Tai、Tadashi Okuyama

  DOI：10.1039/b106850d

  日期：2001.10.23

  Hydroboration of conjugated dienes is promoted by the hydroxy and methoxy groups, which also control the rearrangement of the initially produced allylic boranes.
• Stereoselective hydrogenation of conjugate diene directed by hydroxy group and asymmetric synthesis of deoxypolypropionate units
  作者：Takashi Sugimura、Chun Young Im、Yasuhiro Sato、Tadashi Okuyama

  DOI：10.1016/j.tet.2007.02.128

  日期：2007.5

  Optically active cyclic compounds carrying a conjugate diene and two hydroxy groups were prepared through the intramolecular Buchner reaction with a chiral tether and succeeding stereoselective conversion. Hydrogenation of the diene in the first step was not regio-selective but resulted in three regioisomeric monoenes. Nevertheless. the final saturated product carrying two stereogenic centers could be obtained in 98% stereochemical purity on further hydrogenation under optimized conditions. The high stereoselectivity throughout the multiple pathways is attributable to the effective direction by the hydroxy group. Ring cleavage of the produced stereochemically pure seven-membered ring compounds successfully resulted in synthetic intermediates for deoxypolypropionates. (C) 2007 Elsevier Ltd. All rights reserved.