(E)-6-phenylhex-5-ene-1,4-diol | 59700-95-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-6-phenylhex-5-ene-1,4-diol
• CAS: 59700-95-7
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: ILGUOWDCMOXQHY-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-phenylhex-5-ene-1,4-diol 在 三(五氟苯基)硼烷 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 以82%的产率得到(E)-2-styryltetrahydrofuran
  参考文献：
  名称：

  Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic S_N1 reactions of alcohols

  摘要：

  B(C6F5)3具有与传统的Lewis酸和Brønsted酸不同的反应性/化学选择性特征，并且在存在酸敏感基团的情况下，能够有效地促进醇的催化SN1反应，而不会影响反应速率、底物范围或催化剂负荷。

  DOI：

  10.1039/c4ob01265h
• 作为产物：
  描述：

  methyl 4-oxo-6-phenylhex-5-ynoate 在 lithium aluminium tetrahydride 作用下， 生成 (E)-6-phenylhex-5-ene-1,4-diol
  参考文献：
  名称：

  Robin,R., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1976, vol. 282, p. 281 - 282

  摘要：

  DOI：

文献信息

• Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic Alcohols
  作者：Hongchao Zheng、Sina Ghanbari、Shinji Nakamura、Dennis G. Hall

  DOI：10.1002/anie.201201620

  日期：2012.6.18

  BAC to the future: Boronic acid catalysis (BAC) was applied to the direct activation of alcohols leading to the preparation of carbocycles (see scheme), benzofurans, tetrahydrofurans, pyrrolidines, pyrans, piperidines, and various polycyclic compounds. The reactions proceed under mild conditions that circumvent the use of reactive leaving groups like halides.

  未来的BAC：将硼酸催化（BAC）应用于醇的直接活化，从而制备碳环（参见方案），苯并呋喃，四氢呋喃，吡咯烷，吡喃，哌啶和各种多环化合物。反应在避开反应性离去基团（如卤化物）的温和条件下进行。
• [EN] CHIRAL N-HETEROCYCLIC PHOSPHORODIAMIDIC ACIDS (NHPAS) AND DERIVATIVES AS NOVEL BRONSTED ACID CATALYSTS<br/>[FR] ACIDES PHOSPHORODIAMIDIQUES N-HÉTÉROCYCLIQUES (NHPA) CHIRAUX ET LEURS DÉRIVÉS EN TANT QUE NOUVEAUX CATALYSEURS ACIDES DE BRONSTED
  申请人：THE BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF THE UNIV OF NEVADA LAS VE

  公开号：WO2018232315A1

  公开（公告）日：2018-12-20

  Provided herein are diaryl and arylalkyl phosphonates, useful as intermediates in, for example, the synthesis of leukocyte elastase inhibitors, potassium channel modulators, chemiluminescence materials, and flame retardants, and methods for making same. Also provided are N-heterocyclic phosphorodiamidic acids (NHPAs) useful in reactions such as, for example, in the preparation of diaryl and arylalkyl phosphonates. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文提供了二芳基和芳基烷基膦酸酯，可用作白细胞弹性酶抑制剂、钾通道调节剂、化学发光材料和阻燃剂等合成中间体，并提供了制备方法。同时还提供了N-杂环膦二酰胺酸（NHPAs），可用于反应，例如在制备二芳基和芳基烷基膦酸酯中。本摘要旨在作为特定领域搜索的扫描工具，不限制本发明。
• Intramolecular Etherification and Polyene Cyclization of π-Activated Alcohols Promoted by Hot Water
  作者：Feng-Zhi Zhang、Yan Tian、Guo-Xing Li、Jin Qu

  DOI：10.1021/jo502636d

  日期：2015.1.16

  Hot water, acting as a mildly acidic catalyst, efficiently promoted intramolecular direct nucleophilic substitution reactions of unsaturated alcohols with heteroatom or carbon nucleophiles. In a mixed solvent of water and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), polyene cyclizations using allylic alcohols as initiators gave the desired cyclized products, and in neat HFIP, a tricyclization reaction

  用作弱酸性催化剂的热水有效地促进了不饱和醇与杂原子或碳亲核试剂的分子内直接亲核取代反应。在水和1,1,1,1,3,3,3-六氟-2-丙醇（HFIP）的混合溶剂中，使用烯丙醇作为引发剂进行多烯环化，得到所需的环化产物，在纯HFIP中，进行三环化反应一种四环产物，化学产率为51％。
• Chiral n-heterocyclic phosphorodiamidic acids (NHPAS) and derivatives as novel bronsted acid catalysts
  申请人：The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas

  公开号：US11248014B2

  公开（公告）日：2022-02-15

  Provided herein are diaryl and arylalkyl phosphonates, useful as intermediates in, for example, the synthesis of leukocyte elastase inhibitors, potassium channel modulators, chemiluminescence materials, and flame retardants, and methods for making same. Also provided are N-heterocyclic phosphorodiamidic acids (NHPAs) useful in reactions such as, for example, in the preparation of diaryl and arylalkyl phosphonates. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文提供的是二芳基和芳烷基膦酸盐，可用作例如合成白细胞弹性蛋白酶抑制剂、钾通道调节剂、化学发光材料和阻燃剂的中间体，以及制造方法。此外，还提供了在制备二芳基和芳基烷基膦酸盐等反应中有用的 N-杂环磷酸二酰胺（NHPA）。本摘要旨在作为一种扫描工具，用于特定技术领域的搜索，并不限制本发明。
• Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(−)-sparteine system
  作者：Katsuhiko Tomooka、Nobuyuki Komine、Tomoya Sasaki、Hideo Shimizu、Takeshi Nakai

  DOI：10.1016/s0040-4039(98)02233-3

  日期：1998.12

  Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi /(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). (C) 1998 Elsevier Science Ltd. All rights reserved.