2-Ethenyl-1-phenylnonan-1-ol | 155886-13-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Ethenyl-1-phenylnonan-1-ol
• CAS: 155886-13-8
• 化学式: C₁₇H₂₆O
• 分子量: 246.393
• InChiKey: JMKGUWJARXNMND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  反-5-癸烯醇 、 苯甲醛 在 正丁基锂 、 二氯二茂锆 作用下， 以 乙醚 、 正己烷 为溶剂， 以73%的产率得到2-Ethenyl-1-phenylnonan-1-ol
  参考文献：
  名称：

  不饱和脂肪醇衍生物作为取代的烯丙基锆茂的来源。

  摘要：

  DOI：

  10.1002/anie.200501946

文献信息

• Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents
  作者：Akira Yanagisawa、Yasuhiro Yamada、Hisashi Yamamoto

  DOI：10.1055/s-1997-1530

  日期：1997.9

  An increase of α-regioselectivity was observed in the reaction of allylic barium reagents with aldehydes employing crown ether as an additive. For example, an α/γ regioselectivity was improved to 98/2 from 92/8, when an equimolar amount of 18-crown-6 was added to geranylbarium reagent in THF at -78 °C prior to the reaction with benzaldehyde.

  在含冠醚添加剂的反应中，观察到烯丙基钡试剂与醛的反应中α位选择性增加。例如，当在-78°C下将等摩尔量的18-冠-6加入到在THF中的香叶基钡试剂中，并与苯甲醛反应前，α/γ位选择性从92/8提高到98/2。
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).
• Charge reversal of electrophilic .pi.-allylpalladium intermediates: carbonyl allylation by allylic acetates with tetrakis(triphenylphosphine)palladium-zinc
  作者：Yoshiro Masuyama、Nobuyoshi Kinugawa、Yasuhiko Kurusu

  DOI：10.1021/jo00392a044

  日期：1987.8
• Allylbarium in organic synthesis: unprecedented .alpha.-selective and stereospecific allylation of carbonyl compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Hisashi Yamamoto

  DOI：10.1021/ja00023a058

  日期：1991.11
• Unsaturated Fatty Alcohol Derivatives as a Source of Substituted Allylzirconocene
  作者：Nicka Chinkov、Anat Levin、Ilan Marek

  DOI：10.1002/anie.200501946

  日期：2006.1.9