(5E,3S)-1-phenylpent-3-en-1-ol | 369651-20-7

• 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: (5E,3S)-1-phenylpent-3-en-1-ol
• 英文别名: (S,E)-1-phenylpent-3-en-1-ol；(S,Z)-1-phenylpent-3-en-1-ol；(E,1S)-1-phenylpent-3-en-1-ol
• CAS: 369651-20-7
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: GTPNDSIWHNAACI-VUDBWIFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (5E,3S)-1-phenylpent-3-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Tandem dienyne ring-closing metathesis of alkynyl silaketals for the formation of bicyclic siloxanes

  摘要：

  The tandem dienyne ring-closing metathesis of alkynyl silaketals containing two tethered olefins was achieved with second generation Grubbs NHC-ruthenium carbene complex to provide bicyclic siloxanes in good to excellent yield. Silaketals synthesized from homoallylic or bishomoallylic alcohols via base-catalyzed alcoholysis of trialkynylsilanes were well tolerated in the metathesis process and generated ring systems of various sizes. Removal of the silicon tether was achieved through protodesilylation with fluoride to afford stereochemically defined (1E,3Z)-dienes. (c) 2005 Elsevier B.V. All rights preserved.

  DOI：

  10.1016/j.jorganchem.2005.04.037
• 作为产物：
  描述：

  苯甲醛 、 (1R,2S,5R)-1-((R)-1-methylallyl)menthol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到(5E,3S)-1-phenylpent-3-en-1-ol
  参考文献：
  名称：

  醛通过手性巴豆基供体的烯丙基转移反应进行醛的首个和高度对映选择性的丁酰化。

  摘要：

  DOI：

  10.1021/ja011257f

文献信息

• Hydroxy-Directed Cyclopropanation of Esters: Synthesis of Trisubstituted Cyclopropanols
  作者：Dmitry Astashko、Jin Kun Cha、Nagavaram Narsimha Rao、Bibhuti Bhusan Parida

  DOI：10.1002/ejoc.201301252

  日期：2014.1

  The Kulinkovich cyclopropanation of esters with disubstituted homoallylic alcohols is described for the preparation of 1,2,3-trisubstituted cyclopropanols. Central to the successful implementation is the generation in situ of a temporary alkoxy tether between a homoallylic alcohol and an alkoxytitanium species to override unfavorable steric factors.

  描述了酯与二取代高烯丙醇的 Kulinkovich 环丙烷化反应制备 1,2,3-三取代环丙醇。成功实施的核心是在高烯丙醇和烷氧基钛物种之间原位生成临时烷氧基系链，以克服不利的空间因素。
• Highly Stereoselective Synthesis of<i>Z</i>-Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates
  作者：Celia A. Incerti-Pradillos、Mikhail A. Kabeshov、Andrei V. Malkov

  DOI：10.1002/anie.201300709

  日期：2013.5.10

  α to Z: Racemic α‐chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face‐ and Z‐selective allylation of aldehydes catalyzed by the chiral Brønsted acid (R)‐TRIP (see scheme; Epin=tetraethylethylene glycol).

  α到 Z：外消旋的α-手性烯丙基硼酸酯，很容易从相应的伯烯丙基卤化物合成，在手性布朗斯台德酸（R）-TRIP催化的醛的Z面和Z选择性烯丙基化反应中经历高效的动力学拆分（参见方案； Epin ＝四乙基乙二醇）。
• Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines
  作者：Laura Villar、Nikolai V. Orlov、Nikolay S. Kondratyev、Uxue Uria、Jose L. Vicario、Andrei V. Malkov

  DOI：10.1002/chem.201804395

  日期：2018.11.2

  chromatographically‐stable secondary allyl boronates featuring a 1,1,2,2‐tetraethyl‐1,2‐ethanediol fragment (Epin) were obtained by kinetic resolution of their racemic mixtures. The Epin group at boron considerably improved stability of allyl boronates allowing them to be readily isolated by chromatography on silica. The resolved reagents were applied in stereoselective synthesis of homoallylic amines with an internal

  通过动力学拆分外消旋混合物，可得到高度对映体富集，色谱稳定的仲丁基硼酸仲烷基酯，具有1,1,2,2-四乙基-1,2-乙二醇片段（Epin）。硼上的Epin基团大大提高了烯丙基硼酸酯的稳定性，使它们易于通过硅胶色谱法分离。使用由醛和氨原位形成的未保护的亚胺，将拆分的试剂应用于具有内部双键的均聚烯丙基胺的立体选择性合成中。反应以极好的手性转移进行。
• The First and Highly Enantioselective Crotylation of Aldehydes via an Allyl-Transfer Reaction from a Chiral Crotyl-Donor
  作者：Junzo Nokami、Masanori Ohga、Hitoshi Nakamoto、Tadahiro Matsubara、Iqbal Hussain、Kazuhide Kataoka

  DOI：10.1021/ja011257f

  日期：2001.9.1
• Tandem dienyne ring-closing metathesis of alkynyl silaketals for the formation of bicyclic siloxanes
  作者：Jonathan B. Grimm、Ryan D. Otte、Daesung Lee

  DOI：10.1016/j.jorganchem.2005.04.037

  日期：2005.12

  The tandem dienyne ring-closing metathesis of alkynyl silaketals containing two tethered olefins was achieved with second generation Grubbs NHC-ruthenium carbene complex to provide bicyclic siloxanes in good to excellent yield. Silaketals synthesized from homoallylic or bishomoallylic alcohols via base-catalyzed alcoholysis of trialkynylsilanes were well tolerated in the metathesis process and generated ring systems of various sizes. Removal of the silicon tether was achieved through protodesilylation with fluoride to afford stereochemically defined (1E,3Z)-dienes. (c) 2005 Elsevier B.V. All rights preserved.