(1E)-1-phenyl-1-nonen-4-ol | 138175-92-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1E)-1-phenyl-1-nonen-4-ol
• 英文别名: 1-phenyl-non-1-en-4-ol；(E)-1-phenylnon-1-en-4-ol
• CAS: 138175-92-5
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: FRGQWQUWBGMVKD-DHZHZOJOSA-N

物化性质

• 沸点：
  353.6±21.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-环氧庚烷 、 苯乙炔 生成 (1E)-1-phenyl-1-nonen-4-ol
  参考文献：
  名称：

  氢化锆/金属转移/烷基化：将1-炔烃直接一锅转化为E-1,2-二取代烯烃

  摘要：

  末端乙炔的加氢锆化，然后将中间的锆酸乙烯基酯与较高级的氰铜酸盐进行金属转移，可得到混合的乙烯基铜酸酯，其会与各种亲电试剂进行烷基化反应。

  DOI：

  10.1016/s0040-4039(00)93519-6

文献信息

• Development of a Highly α-Regioselective Metal-Mediated Allylation Reaction in Aqueous Media:  New Mechanistic Proposal for the Origin of α-Homoallylic Alcohols
  作者：Kui-Thong Tan、Shu-Sin Chng、Hin-Soon Cheng、Teck-Peng Loh

  DOI：10.1021/ja029276s

  日期：2003.3.1

  This paper described a general method to obtain α-adduct homoallylic alcohols using indium, zinc, and tin in water. A new mechanism was proposed to account for the formation of these synthetically difficult-to-obtain molecules. Generally, this method can be performed with a wide range of aldehydes and allylic halides with just 6 equiv of water added, giving the α-adduct in high selectivities. To account

  本文描述了使用水中的铟、锌和锡获得 α-加合物高烯丙醇的一般方法。提出了一种新机制来解释这些合成上难以获得的分子的形成。通常，该方法可以使用各种醛和烯丙基卤化物进行，只需添加 6 当量的水，从而以高选择性得到 α-加合物。为了解释 α-高烯丙基醇的起源，使用 1H NMR、交叉实验和 22β γ-加合物高烯丙基甾醇转化为 22α α-加合物高烯丙基甾醇的立体化学研究仔细研究了反应机理。从机理研究结果来看，金属介导的α-区域选择性烯丙基化可能存在两种机制途径共存。
• Development of a highly α-regioselective indium-mediated allylation reaction in water
  作者：Teck-Peng Loh、Kui-Thong Tan、Jian-Ying Yang、Chao-Li Xiang

  DOI：10.1016/s0040-4039(01)01883-4

  日期：2001.12

  Linear alpha homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic in origin from the results presented in this paper. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Performance of SCS Palladium Pincer Complexes in Borylation of Allylic Alcohols. Control of the Regioselectivity in the One-Pot Borylation−Allylation Process
  作者：Nicklas Selander、Kálmán J. Szabó

  DOI：10.1021/jo9008673

  日期：2009.8.7

  One-pot borylation-allylation reactions of aldehydes and allylic alcohols were performed under various reaction conditions. The borylation of allylic alcohols was performed using a very efficient SCS palladium pincer-complex catalyst. The regioselectivity of the allylation depends on the applied solvent. The reaction in CHCl3 gave the linear allylic product; however, when MeOH was added to the reaction mixture, the branched allylic product was formed.
• The First In(OTf)3-Catalyzed Conversion of Kinetically Formed Homoallylic Alcohols into the Thermodynamically Preferred Regioisomers: Application to the Synthesis of 22α-Sterols
  作者：Teck-Peng Loh、Kui-Thong Tan、Qi-Ying Hu

  DOI：10.1002/1521-3773(20010803)40:15<2921::aid-anie2921>3.0.co;2-v

  日期：2001.8.3

  A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3 -catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.