(+/-)-(E)-2,6-dimethylhept-4-en-3-ol | 121440-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(E)-2,6-dimethylhept-4-en-3-ol
• 英文别名: (E)-2,6-Dimethylhept-4-en-3-ol；(E)-2,6-dimethyl-4-hepten-3-ol
• CAS: 121440-79-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: BDEWQLXPXANDJE-AATRIKPKSA-N

物化性质

• 沸点：
  167.7±8.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-2,6-dimethylhept-4-en-3-ol 在 正丁基锂 、 bis(η3-allyl-μ-chloropalladium(II)) 、 (-)-(S)-2-<2-(diphenylphosphino)phenyl>-4-tert-butyl-3,4-dihydrooxazole 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 219.17h， 生成 (-)-tert-butyl-N-<1-(1'-methylethyl)-4-methyl-2-pentenyl>iminocarboxylate
  参考文献：
  名称：

  Enantioselective allylic amination with chiral (phosphino-oxazoline)pd catalysts

  摘要：

  Chiral (phosphinophenyl-oxazoline)palladium complexes have been studied as enantioselective catalysts for allylic amination using benzylamine or the sodium salts of p-toluenesulfonamide, benzoylhydrazine, and (Boc)(2)NH as nucleophiles. In the reactions with 1,3-diphenyl- and 1,3-dialkyl-2-propenyl acetates, carbonates, or phosphates, moderate to high enantiomeric excesses of up to 97% have been obtained.

  DOI：

  10.1016/0957-4166(94)80021-9
• 作为产物：
  描述：

  2,6-二甲基-4-庚炔-3-醇 在 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 以68%的产率得到(+/-)-(E)-2,6-dimethylhept-4-en-3-ol
  参考文献：
  名称：

  Hoffmann, Reinhard W.; Julius, Manfred, Liebigs Annalen der Chemie, 1991, # 8, p. 811 - 822

  摘要：

  DOI：

文献信息

• Palladium(0)-Catalyzed Enantioselective <i>O</i>,<i>S</i>-Rearrangement of Racemic <i>O</i>-Allylic Thiocarbamates:  A New Entry to Enantioenriched Allylic Sulfur Compounds
  作者：Hans-Joachim Gais、Achim Böhme

  DOI：10.1021/jo010668b

  日期：2002.2.1

  operation from the corresponding N-methyl S-allylic thiocarbamate through a palladium(0)-catalyzed substitution of iodobenzene in the presence of a base. The palladium(0)-catalyzed enantioselective rearrangement of O-allylic carbamates to S-allylic carbamates has been extended from the solution phase to the solid phase by using a methyl thioisocyanate polystyrene resin. In the case investigated the enantioselectivity

  （+/-）-（E）-戊-3-烯-2-醇，（+/-）-（E）-庚-4-烯-3-醇，（+/-）-（E ）-2,6-二甲基庚-4-烯-3-醇，（+/-）-环己-2-烯-1-醇和（+/-）-环庚-2-烯-1-醇与甲基异硫氰酸乙基，正丙基，异丙基，正丁基，叔丁基和苄基异氰酸酯以中等收率得到相应的外消旋O-烯丙基硫代氨基甲酸酯，具有良好的热稳定性。（+/-）-（E）-pent-3-en-2-ol-，（+/-）-（E）-hept-4-en-3-ol的钯（0）催化重排使用Pd2在室温下于室温下将-，（+/-）-环己-2-烯-1-醇和（+/-）-环庚-2-烯-1-醇衍生的O-烯丙基硫代氨基甲酸酯（dba）3 * CHCl3（dba =二亚苄基丙酮）作前催化剂和（+）-（1R，2R）-1,2-双-N-（（2-（二苯基膦基）苯甲酰基）-1，定量进行2-二氨基环己烷作为钯原子的配体，得到相应的无环（R）构型的S-
• Electronic effects on π-facial stereoselectivity in electrophilic additions to allylic bonds: stereoselective epoxidation of allylic fluorides
  作者：Makoto Fujita、Hidemi Ishizuka、Katsuyuki Ogura

  DOI：10.1016/0040-4039(91)80168-6

  日期：1991.10

  The electronic stabilization of the transition state in electrophilic additions to allylic bonds is discussed through m-CPBA oxidation of allylic fluorides; the stereoselectivity is interpreted by a transition-state model where the most electronegative atom (fluorine) is oriented at the inside position as supported by theoretical examinations.

  通过对烯丙基氟化物的m -CPBA氧化，讨论了对烯丙基键进行亲电子加成时过渡态的电子稳定化；立体选择性由过渡状态模型解释，在过渡状态模型中，最负电性的原子（氟）在理论研究的支持下位于内部位置。
• Asymmetric synthesis catalyzed by chiral ferrocenylphosphine - transition-metal complexes. 8. Palladium-catalyzed asymmetric allylic amination
  作者：Tamio Hayashi、Akihiro Yamamoto、Yoshihiko Ito、Eriko Nishioka、Hitoshi Miura、Kazunori Yanagi

  DOI：10.1021/ja00198a048

  日期：1989.8
• Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs
  作者：Sunghee Son、Gregory C. Fu

  DOI：10.1021/ja800103z

  日期：2008.3.1

  Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A(1).
• Asymmetric synthesis of (3R,5R)- and (3S,5S)-2,6-dimethylheptane-3,5-diol, useful C2 chiral auxiliaries
  作者：C. Jacoby、J.C. Braekman、D. Daloze

  DOI：10.1016/0957-4166(95)00071-v

  日期：1995.3

  (R,R)- and (S,S)-2,6-Dimethylheptane-3,5-diol, which are useful C-2 chiral auxiliaries, have been both synthesized in high optical purity from 2,6-dimethylheptane-3,5-dione, by using as key step a Sharpless kinetic resolution.