(2S,3R,4S)-2-(benzyloxy)-4-methyl-5-hexen-3-ol | 109430-17-3

• 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: (2S,3R,4S)-2-(benzyloxy)-4-methyl-5-hexen-3-ol
• 英文别名: (2S,3R,4S)-4-methyl-2-phenylmethoxyhex-5-en-3-ol
• CAS: 109430-17-3
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XNDKLMZGNVWKGI-SGMGOOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2-(benzyloxy)-4-methyl-5-hexen-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以90%的产率得到(2R,3S,4R)-4-Methyl-hexane-2,3-diol
  参考文献：
  名称：

  Stereochemical aspects of the additions of anti-selective, crotyl organometallic reagents to .alpha.-alkoxy aldehydes

  摘要：

  DOI：

  10.1021/jo00287a032
• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 、 [(Z)-but-2-enyl]-bis[(1S,2S,3S,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane 以78%的产率得到
  参考文献：
  名称：

  BROWN, HERBERT C.;BHAT, KRISHNA S.;RANDAD, RAMNARAYAN S., J. ORG. CHEM., 54,(1989) N, C. 1570-1576

  摘要：

  DOI：

文献信息

• Effect of Substituents on the Ring-Closing Metathesis Reaction in the Synthesis of Functionalized Nonanolactones
  作者：Rosario Hernández-Galán、Jacinto Ramírez-Fernández、Isidro Collado

  DOI：10.1055/s-2008-1032072

  日期：2008.2

  The synthesis of functionalized nine-membered ring lactones based on sequential esterification and ring-closing metathesis (RCM) reactions is reported. The effects of olefin substitution and allylic and homoallylic oxygenated substituents on the RCM reaction is analyzed. An unusual cyclization stereochemistry has been observed, leading to a stereoselective olefin formation in the synthesis of nonanolactones

  报道了基于顺序酯化和闭环复分解 (RCM) 反应的功能化九元环内酯的合成。分析了烯烃取代和烯丙基和高烯丙基氧化取代基对RCM反应的影响。观察到一种不寻常的环化立体化学，导致在壬内酯合成中形成立体选择性烯烃。高选择性可以通过均烯丙基或烯丙基羟基与钌金属中心在钌环丁烷中间体中的相互作用/配位来合理化。
• Anomalous threo-diastereoselectivity in allylic silane- or stannane–aldehyde condensation reactions: new interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations
  作者：Koichi Mikami、Kazuya Kawamoto、Teck-Peng Loh、Takeshi Nakai

  DOI：10.1039/c39900001161

  日期：——

  Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

  在螯合条件下，β-取代的巴豆基硅烷或锡烷与2-苄氧基丙醛的分子间反应中观察到了不寻常的苏-非对映选择性，这表明对苯二酚的偏爱于反平面的过渡态。
• Chiral synthesis via organoboranes. 21. Allyl- and crotylboration of .alpha.-chiral aldehydes with diisopinocampheylboron as the chiral auxiliary
  作者：Herbert C. Brown、Krishna S. Bhat、Ramnarayan S. Randad

  DOI：10.1021/jo00268a017

  日期：1989.3
• Allylcopper Intermediates with N-Heterocyclic Carbene Ligands: Synthesis, Structure, and Catalysis
  作者：Vincenzo Russo、Jessica R. Herron、Zachary T. Ball

  DOI：10.1021/ol902458v

  日期：2010.1.15

  Allylcopper intermediates with N-heterocyclic carbene ligands are synthesized by transmetalation of allylsiloxane reagents, and the crystal structures of allylcopper compounds are reported. The allylcopper transmetalation is utilized for catalytic aldehyde allylation, which is found to be facilitated by a trifluorosilane co-catalyst.
• Macrocyclic picolinamides as fungicides
  申请人：DOW AGROSCIENCES LLC

  公开号：US20170334934A1

  公开（公告）日：2017-11-23

  This disclosure relates to macrocyclic picolinamides of Formula I and their use as fungicides.