4,4,5-trimethyl-1-phenyl-hex-5-en-3-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: 4,4,5-trimethyl-1-phenyl-hex-5-en-3-ol
• 英文别名: 4,4,5-Trimethyl-1-phenylhex-5-en-3-ol
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: HHZRTKXIMYMSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  5
• 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：

  苯丙醛 、 2,3-二甲基-1,3-丁二烯 在 dichloroindium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以88%的产率得到4,4,5-trimethyl-1-phenyl-hex-5-en-3-ol
  参考文献：
  名称：

  通过1,3-二烯的加氢精制和与羰基化合物的一锅法反应生成烯丙基铟。

  摘要：

  通过二氯氢化铟（HInCl2）对1,3-二烯进行加氢精制会生成烯丙基铟，它们在一键处理中会与羰基或亚胺基反应。前者以自由基方式进行，后者是离子烯丙基化。而且，两个反应都不需要添加剂，例如自由基引发剂，路易斯酸或过渡金属催化剂。

  DOI：

  10.1021/ol061797n

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。
• Transition-Metal-Free Reductive Coupling of 1,3-Butadienes with Aldehydes Catalyzed by Dibutyliodotin Hydride
  作者：Itaru Suzuki、Yuki Uji、Shujiro Kanaya、Ryosuke Ieki、Shinji Tsunoi、Ikuya Shibata

  DOI：10.1021/acs.orglett.7b02671

  日期：2017.10.6

  In this study, the Bu2SnIH-catalyzed direct coupling of 1,3-dienes with aldehydes was developed. This reaction could be suitable for coupling without the use of transition-metal catalysts. Many types of aldehydes were applied to this reaction. The addition of MeOH promoted the catalytic cycle.

  在这项研究中，开发了Bu 2 SnIH催化的1,3-二烯与醛的直接偶联。该反应可以适合于不使用过渡金属催化剂的偶联。许多类型的醛被用于该反应。MeOH的加入促进了催化循环。
• Regiocontrolled Addition of Carbonyl Compounds with Allylic Indium Generated by Hydroindation of 1,3-Dienes
  作者：Ikuya Shibata、Akio Baba、Naoki Hayashi、Hiroyuki Honda、Makoto Yasuda

  DOI：10.1055/s-2008-1072753

  日期：2008.5

  Allylic indiums, generated by a conjugate hydroindation of 1,3-dienes by HInCl2, reacted with carbonyl compounds in a one-pot treatment. Both γ- and α-adducts can be obtained depending upon the conditions used.

  通过HInCl2对1,3-二烯进行共轭氢铟化反应生成的烯丙基铟，在一锅法处理中与羰基化合物反应。根据所使用的条件，可以获得γ-加合物和α-加合物。
• Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
  作者：Shu Kobayashi、Koichi Nishio

  DOI：10.1021/jo00101a021

  日期：1994.11

  Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields. The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively. In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly. Solvent effects in these reactions were also examined. The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates. While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, antihomoallylic alcohols were obtained from (E)-allyl chlorides. Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found. Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.
• 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：——