3-methyl-1-phenyl-1-hepten-3-ol | 99431-00-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-methyl-1-phenyl-1-hepten-3-ol
• 英文别名: (E)-3-methyl-1-phenylhept-1-en-3-ol
• CAS: 99431-00-2
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: XMKLPICZPKZZGP-ZRDIBKRKSA-N

物化性质

• 沸点：
  325.4±11.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  正丁基锂 、 苄叉丙酮 在 mischmetall triiodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以98%的产率得到3-methyl-1-phenyl-1-hepten-3-ol
  参考文献：
  名称：

  杂金属在有机合成中的一些用途

  摘要：

  Mischmetall是一种轻型镧系元素的合金，已用于多种有机反应中，作为sa（II）介导的反应（巴比尔和格利雅德型反应，松香偶联反应）的共轭物或Reformatsky-的促进剂。类型反应。它也被用作容易合成镧系三卤化物的起始原料，在今元和Luche-Fukuzawa反应以及Mukaiyama aldol反应中已经探究了其反应活性。

  DOI：

  10.1016/j.tet.2003.07.017

文献信息

• New chiral ligands for the asymmetric copper catalyzed conjugate addition of Grignard reagents to enones
  作者：Eric L. Stangeland、Tarek Sammakia

  DOI：10.1016/s0040-4020(97)01031-4

  日期：1997.12

  The copper catalyzed conjugate addition of n-butyl Grignard to enones in the presence of chiral ferrocenyl phosphine oxazoline ligands has been studied and found to provide useful levels of asymmetric induction. A comparison of the ferrocene derived ligands 3 and 6 with the corresponding phenyl derived ligands 8 and 9 reveals that the ferrocene template plays an essential role in the reaction.

  已经研究了在手性二茂铁基膦膦恶唑啉配体的存在下，铜催化的正丁基格氏试剂向烯酮的共轭加成反应，并发现其提供了有用的不对称诱导水平。二茂铁衍生的配体3和6与相应的苯基衍生的配体8和9的比较表明，二茂铁模板在反应中起重要作用。
• Process for the preparation of N-hydrocarbyl-substituted amides
  申请人：The Lubrizol Corporation

  公开号：EP0846678A1

  公开（公告）日：1998-06-10

  Hydrocarbyl-substituted amides can be prepared in a catalyzed Ritter reaction by contacting a nitrile with a hydrocarbylating agent, in the presence of an acidified clay as the catalyst, under conditions conducive to the formation of the hydrocarbyl-substituted amide.

  在有利于形成烃基取代酰胺的条件下，在酸化粘土作为催化剂存在的情况下，通过腈与烃基化剂接触，可在催化里特反应中制备烃基取代酰胺。
• Samarium(II) Triflate as a New Reagent for the Grignard-Type Carbonyl Addition Reaction
  作者：Shin-ichi Fukuzawa、Keisuke Mutoh、Teruhisa Tsuchimoto、Tamejiro Hiyama

  DOI：10.1021/jo960260s

  日期：1996.1.1

  On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.
• Holm, Torkil, Acta Chemica Scandinavica, 1991, vol. 45, # 9, p. 925 - 929
  作者：Holm, Torkil

  DOI：——

  日期：——
• Some Observations on the Mechanism of Diorganocuprate 1,4-Addition Reactions with α,β-Unsaturated Ketones:  Effects of Diethyl Ether in Reactions of Butylcoppers in Toluene
  作者：Celia L. Kingsbury、Robin A. J. Smith

  DOI：10.1021/jo970316y

  日期：1997.7.1

  Mixtures of butyllithium and copper iodide prepared in toluene react with alpha,beta-unsaturated ketones predominantly in a 1,2-fashion. Addition of 2 equiv of diethyl ether to the system results in a dramatic preference for the 1,4-product, as found normally with diorganocuprates in ethereal solvents. These results are in accordance with the theoretical predictions that a suitable ligand is required to facilitate the stabilization of a formally copper(III) reaction intermediate on the 1,4-addition mechanistic pathway.