(E)-1-p-Tolyl-pent-3-en-1-ol | 150712-82-6

• 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: (E)-1-p-Tolyl-pent-3-en-1-ol
• 英文别名: 1-(4-Methylphenyl)pent-3-en-1-ol
• CAS: 150712-82-6
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: HQEDQJYKGUPUJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  对甲基苯甲醛 、 magnesium,but-1-ene,bromide 以 二氯甲烷 为溶剂， 生成 (E)-1-p-Tolyl-pent-3-en-1-ol
  参考文献：
  名称：

  关于烯丙基锡试剂-苯甲醛缩合的反应途径和立体化学。替代效应研究

  摘要：

  对路易斯酸介导的烯丙基和巴豆基锡烷与芳醛加成的反应性和立体选择性的取代基效应研究表明，该反应通过极性反周向过渡态进行，2,4,6-三甲基苯甲醛除外，其循环途径与开放路径竞争。

  DOI：

  10.1246/cl.1990.1711

文献信息

• SnCl2-mediated carbonyl allylation of aldehydes and ketones in ionic liquid
  作者：Long Tang、Li Ding、Wei-Xing Chang、Jing Li

  DOI：10.1016/j.tetlet.2005.11.022

  日期：2006.1

  In ionic liquid [bmim]BF4, SnCl2·2H2O acts as an inexpensive and efficient metal salt for carbonyl allylation. By applying ionic liquid, some previously reported serious operational problems associated with the SnCl2-mediated allylation reaction are avoided. Furthermore, ketones, which are less reactive than aldehydes, can also be allylated in high yields with this system.

  在离子液体[bmim] BF 4中，SnCl 2 ·2H 2 O作为一种廉价而有效的羰基烯丙基化金属盐。通过施加离子液体，避免了一些先前报道的与SnCl 2介导的烯丙基化反应相关的严重操作问题。此外，与该醛相比反应性较弱的酮也可以通过该系统以高收率烯丙基化。
• [EN] PROCESSES FOR HIGHLY ENANTIO-AND DIASTEREOSELECTIVE SYNTHESIS OF ACYCLIC EPOXY ALCOHOLS AND ALLYLIC EPOXY ALCOHOLS<br/>[FR] PROCEDES DE SYNTHESE HAUTEMENT ENANTIOSELECTIVE ET DIASTEREOSELECTIVE D'EPOXYALCOOLS ACYCLIQUES ET D'EPOXYALCOOLS ALLYLIQUES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2005087755A1

  公开（公告）日：2005-09-22

  The inventive subject matter relates to novel processes for making an epoxy alcohol from an aldehyde, comprising the steps of: (a) adding (i) an organozinc compound or (ii) divinylzinc compound and an diorganozinc compound to said aldehyde in the presence of a first catalyst to form an allylic alkoxide compound; and (b) epoxidizing said allylic alkoxide compound in the presence of an oxidant and a second catalyst.

  发明主题涉及从醛制备环氧醇的新颖工艺，包括以下步骤：(a) 在第一催化剂的存在下，向所述醛中添加(i)有机锌化合物或(ii)二乙烯基锌化合物和二有机锌化合物，以形成烯丙基烷氧基化合物；以及(b) 在氧化剂和第二催化剂的存在下，将所述烯丙基烷氧基化合物环氧化。
• Iridium-Catalyzed Carbonyl Allylations by Allylic Alcohols with Tin(II) Chloride
  作者：Yoshiro Masuyama、Toshiya Chiyo、Yasuhiko Kurusu

  DOI：10.1055/s-2005-872255

  日期：——

  Iridium complex [IrCl(cod)] 2 can function as a catalyst for the allylation of aldehydes and ketones by allylic alcohols upon addition of an equimolar amount of SnCl 2 in THF-H 2 O; the reaction is carried out between roomtemperature and 50 °C to give the corresponding homoallylic alcohols.

  铱络合物[IrCl(cod)] 2 可作为烯丙醇烯丙基化醛和酮的催化剂，在THF-H 2 O中加入等摩尔量的SnCl 2 ；反应在室温和 50 °C 之间进行，得到相应的高烯丙醇。
• α-Regioselective carbonyl allylation by an allylic tin compound prepared from 1-bromobut-2-ene and tin(<scp>II</scp>) bromide at a nonpolar organic–aqueous interface
  作者：Yoshiro Masuyama、Masayuki Kishida、Yasuhiko Kurusu

  DOI：10.1039/c39950001405

  日期：——

  1-Bromobut-2-ene on a dichloromethane–water biphasic system at 25 °C causes α-regioselective addition to aldehydes with SnBr2 to produce 1-substituted pent-3-en-1-ols, and causes γ-regioselective addition to aldehydes with SnBr2–Bu4NBr to produce 1-substituted 2-methylbut-3-en-1-ols.

  在25°C的二氯甲烷-水双相系统上，1-溴丁-2-烯引起醛与SnBr 2的α-区域选择性加成，生成1-取代的戊-3-烯-1-醇，并引起γ-区域选择性加成。与SNBR醛2 -Bu 4 NBR，以产生1-取代2-甲基丁-3-烯-1-醇。
• Processes for Highly Enantio- and Diastereoselective Synthesis of Acyclic Epoxy Alcohols and Allylic Epoxy Alcohols
  申请人：Walsh Patrick

  公开号：US20090163728A1

  公开（公告）日：2009-06-25

  The inventive subject matter relates to novel processes for making an epoxy alcohol from an aldehyde, comprising the steps of: (a) adding (i) an organozinc compound or (ii) divinylzinc compound and an diorganozinc compound to said aldehyde in the presence of a first catalyst to form an allylic alkoxide compound; and (b) epoxidizing said allylic alkoxide compound in the presence of an oxidant and a second catalyst.

  本发明涉及一种从醛制备环氧醇的新工艺，包括以下步骤：(a)在第一催化剂的存在下向所述醛中加入(i)有机锌化合物或(ii)二乙烯基锌化合物和二有机锌化合物，以形成烯丙氧化物化合物；(b)在氧化剂和第二催化剂的存在下使烯丙氧化物化合物环氧化。