(2R^*,3S^*,4S^*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol | 124377-75-9

• 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: (2R^*,3S^*,4S^*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol
• 英文别名: threo-BnOCHMeCH(OH)CH(CH3)CHCH2；(2S,3R,4R)-4-methyl-2-phenylmethoxyhex-5-en-3-ol
• CAS: 124377-75-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XNDKLMZGNVWKGI-MBNYWOFBSA-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：

  (2R^*,3S^*,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-methylhexane-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 、 (-)-(E)-crotyldiisopinocamphenylborane 以4%的产率得到
  参考文献：
  名称：

  BROWN, H. C.;BHAT, K. S.;RANDAD, K. S., J. ORG. CHEM., 52,(1987) N 16, 3701-3702

  摘要：

  DOI：

文献信息

• 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。
• Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to α-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems
  作者：Leo A. Paquette、Thomas M. Mitzel

  DOI：10.1021/jo9613489

  日期：1996.1.1

  The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted a-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti,syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and ''anti-Felkin'' transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.
• 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.
• BROWN, HERBERT C.;BHAT, KRISHNA S.;RANDAD, RAMNARAYAN S., J. ORG. CHEM., 54,(1989) N, C. 1570-1576
  作者：BROWN, HERBERT C.、BHAT, KRISHNA S.、RANDAD, RAMNARAYAN S.

  DOI：——

  日期：——