2,3-dimethyl-1-phenylbut-3-en-1-ol

• 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: 2,3-dimethyl-1-phenylbut-3-en-1-ol
• 英文别名: (1R,2R)-2,3-dimethyl-1-phenylbut-3-en-1-ol
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: HDCNWWBNSUZFHM-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  (E)-乙酸-2-甲基-2-丁烯酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 生成 2,3-dimethyl-1-phenylbut-3-en-1-ol 、 2,3-dimethyl-1-phenylbut-3-en-1-ol
  参考文献：
  名称：

  Ni- and Pd-Catalyzed Synthesis of Substituted and Functionalized Allylic Boronates

  摘要：

  Two highly efficient and convenient methods for the synthesis of functionalized and substituted allylic boronates are described. In one procedure, readily available allylic acetates are converted to allylic boronates catalyzed by Ni/PCy3 or Ni/PPh3 complexes with high levels of stereoselectivity and in good yields. Alternatively, the borylation can be accomplished with commercially available Pd catalysts [e.g., Pd-2(dba)(3), PdCl2, Pd/C], starting with easily accessed allylic halides.

  DOI：

  10.1021/ol3001552

文献信息

• Rh-Catalyzed Reductive Coupling Reaction of Aldehydes with Conjugated Dienes Promoted by Triethylborane
  作者：Masanari Kimura、Daisuke Nojiri、Masahiro Fukushima、Shuichi Oi、Yusuke Sonoda、Yoshio Inoue

  DOI：10.1021/ol901527b

  日期：2009.9.3

  Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.

  在化学计量的三乙基硼烷存在下，Rh（I）催化多种醛与共轭二烯的还原偶联反应，只需一次操作即可提供均烯丙基醇。
• Reversal of <i>Anti</i> to <i>Syn</i> Diastereoselectivity in Crotyltitanation Reaction
  作者：Jan Szymoniak、Nadine Thery、Claude Moïse

  DOI：10.1055/s-1997-1002

  日期：1997.11

  η3-2-Methylcrotyl(tiglyl)titanocene reacts with aldehydes to afford anti homoallylic alcohols when the reaction is carried out in THF, and preferentially syn products when the solvent is HMPA/THF=3:1. This simple control of anti versus syn diastereoselectivity expands considerably the synthetic uses of the crotyltitanation reaction.

  η3-2-甲基克罗提尔（提基尔）钛烯与醛反应时，在THF溶剂中生成反式同伴醇，而在HMPA/THF=3:1的溶剂中则优先生成顺式产物。这种简单的反式与顺式非对映选择性的控制大大扩展了克罗提尔钛化反应的合成用途。
• Chiral Phosphoric Acid-Catalyzed Enantio- and Diastereoselective Allylboration of Aldehydes with β,γ-Substituted Allylboronates
  作者：Jinping Yuan、Pankaj Jain、Jon C. Antilla

  DOI：10.1021/acs.joc.2c00764

  日期：2022.6.17

  The catalytic asymmetric addition of β,γ-substituted allylboronates to aldehydes has been described. Promoted by 5 mol % chiral phosphoric acid, the reactions were broadly applicable, scalable, and efficient, allowing for the formation of 3,4-anti/syn-homoallylic alcohols bearing adjacent tertiary or quaternary stereogenic centers in a highly enantio- and diastereoselective manner (≤99% ee and dr >20:1)

  已经描述了 β,γ-取代的烯丙基硼酸酯对醛的催化不对称加成。在 5 mol% 手性磷酸的促进下，该反应具有广泛的适用性、可扩展性和高效性，允许以高度对映和非对映选择性的方式形成带有相邻叔或季立体中心的 3,4-反/同-高烯丙醇（≤99% ee 和 dr >20:1）。涉及手性磷酸的刚性椅子状过渡态有助于高度控制的反应。
• One-Pot Synthesis of Homoallylic Alcohols from 1,3-Dienes: Tandem Vicinal Difunctionalization of 1,3-Dienes by Hydride Addition-Aldehyde Coupling Sequence via Organosilicon Intermediates
  作者：Shū Kobayashi、Koichi Nishio

  DOI：10.1055/s-1994-25497

  日期：——
• First Practical Hydrozincation of Dienes Catalyzed by Cp2TiCl2. Generation of Allylzinc Reagent and Its Reaction with Carbonyl Compounds
  作者：Yuan Gao、Hirokazu Urabe、Fumie Sato

  DOI：10.1021/jo00098a005

  日期：1994.9

  The first practical hydrozincation of butadiene and 2-alkylbutadienes has been achieved by a combination reagent including ZnI2, LiH, and Cp(2)TiCl(2) in a ratio of 1:2.2:0.1 to yield the corresponding allylzinc reagents in THF, which, in turn, react with a variety of carbonyl compounds.