3-methyl-1-phenyl-1-hepten-3-ol | 91671-45-3

• 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: 1-phenyl-3-methyl-3-hydroxy-1-heptene；3-methyl-1-phenylhept-1-en-3-ol
• CAS: 91671-45-3
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: XMKLPICZPKZZGP-UHFFFAOYSA-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 lithium bromide 、 氯化铵 作用下， 以 2-甲基四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.0h， 以91%的产率得到3-methyl-1-phenyl-1-hepten-3-ol
  参考文献：
  名称：

  Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and eco-friendly access to allylic alcohols and amines

  摘要：

  Very high regioselective 1,2-addition of organolithiums to alpha,beta-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.067

文献信息

• Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics
  作者：Lauren M. Fleury、Andrew D. Kosal、James T. Masters、Brandon L. Ashfeld

  DOI：10.1021/jo301726v

  日期：2013.1.18

  transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields

  本文介绍的研究描述了一种通过钛茂催化剂介导的格氏试剂和有机锌试剂的还原性过渡金属化方法。该方法能够在不损失官能团相容性的情况下金属化官能化的基材。烯丙基锌试剂和烯丙基，乙烯基和烷基格氏试剂原位生成，并用于加成羰基底物，以提供相应的甲醇，收率高达99％。研究发现，膦配体可有效地促进还原性金属转移反应，从而在低至−40°C的温度下实现C–X键的金属化。在手性二胺和氨基醇的存在下进行反应导致醛的对映选择性烯丙基化。
• Application of indium ate complexes to synthetic chemistry. Selective conjugate addition to enones and coupling with allylic halides
  作者：Shuki Araki、Toshio Shimizu、Shun-Ji Jin、Yasuo Butsugan

  DOI：10.1039/c39910000824

  日期：——

  Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with α,β-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of head-to-tail 1,5-dienes.

  通过向三烷基铟中添加有机锂试剂制备的四有机铟盐配合物，与α，β-不饱和酮以1,4-加成方式反应；衍生自烯丙基倍半卤化铟与烯丙基卤化物在区域和立体上偶合的烯丙基吲哚，可产生高产率的头尾1，5-二烯。
• Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones an efficient method for the synthesis of tertiary alcohols
  作者：Tsuneo Imamoto、Nobuyuki Takiyama、Kimikazu Nakamura

  DOI：10.1016/s0040-4039(00)94945-1

  日期：1985.1

  In the presence of anhydrous cerium(III) chloride, Grignard reagents react with Ketones to afford addition products in high yields, even though the substrates are susceptible to abnormal reactions with Grignard reagents alone.

  在无水氯化铈（III）的存在下，格氏试剂与酮反应以高收率提供加成产物，即使底物仅与格氏试剂容易发生异常反应。
• Reactions of carbonyl compounds with Grignard reagents in the presence of cerium chloride
  作者：Tsuneo Imamoto、Nobuyuki Takiyama、Kimikazu Nakamura、Toshihiko Hatajima、Yasuo Kamiya

  DOI：10.1021/ja00194a037

  日期：1989.6

  The addition of Grignard reagents to ketones is significantly enhanced by cerium chloride with remarkable suppression of side reactions, particularly enolization. Some esters, which are prone to side reactions, also react readily with Grignard reagents in the presence of cerium chloride to give normal reaction products in reasonable to high yields.

  氯化铈显着增强了格氏试剂向酮中的添加，显着抑制了副反应，尤其是烯醇化。一些易于发生副反应的酯在氯化铈存在下也很容易与格氏试剂反应，以合理到高产率得到正常反应产物。
• Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents
  作者：Tsuneo Imamoto、Tetsuo Kusumoto、Yoshinori Tawarayama、Yasushi Sugiura、Takeshi Mita、Yasuo Hatanaka、Masataka Yokoyama

  DOI：10.1021/jo00195a006

  日期：1984.10