(S,R)-2-methyl-5-(phenylmethoxy)hex-1-en-4-ol | 130323-29-4

• 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: (S,R)-2-methyl-5-(phenylmethoxy)hex-1-en-4-ol
• 英文别名: (2S,3R)-5-methyl-2-phenylmethoxyhex-5-en-3-ol
• CAS: 130323-29-4
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: RUZVBDZLKIQYHI-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 、 异丁烯 在 (R)-BINOL-Ti 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到(S,R)-2-methyl-5-(phenylmethoxy)hex-1-en-4-ol
  参考文献：
  名称：

  Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. Syn-diastereofacial preference in anomalous nonchelation complexation

  摘要：

  An anomalous nonchelation diastereofacial selectivity is observed in the titanium-catalyzed carbonyl addition reaction to benzyl-protected alkoxyaldehydes. There is a dichotomy in the sense of syn- vs. anti-diastereofacial preference, dictated by the bulkiness of the migratory group: The sterically demanding silyl group gives syn-diastereofacial preference and the less sterically demanding proton lends to anti-diastereofacial preference. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00231-1

文献信息

• Acyclic stereoselection. 22. Diastereofacial selectivity in the Lewis acid mediated reactions of allylsilanes with chiral aldehydes and enones
  作者：Clayton H. Heathcock、Syunichi Kiyooka、Todd A. Blumenkopf

  DOI：10.1021/jo00196a022

  日期：1984.11
• 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.
• Acyclic stereocontrol based on chelation-controlled ene reaction with chiral α- and β-alkoxyaldehydes
  作者：Koichi Mikami、Teck-Peng Loh、Takeshi Nakai

  DOI：10.1016/s0957-4166(00)82265-x

  日期：1990.1
• Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. Syn-diastereofacial preference in anomalous nonchelation complexation
  作者：Koichi Mikami、Satoru Matsukawa、Eiji Sawa、Akinori Harada、Nobuaki Koga

  DOI：10.1016/s0040-4039(97)00231-1

  日期：1997.3

  An anomalous nonchelation diastereofacial selectivity is observed in the titanium-catalyzed carbonyl addition reaction to benzyl-protected alkoxyaldehydes. There is a dichotomy in the sense of syn- vs. anti-diastereofacial preference, dictated by the bulkiness of the migratory group: The sterically demanding silyl group gives syn-diastereofacial preference and the less sterically demanding proton lends to anti-diastereofacial preference. (C) 1997 Elsevier Science Ltd.