苯甲醇,a-[(2E)-3,7-二甲基-2,6-辛二烯基]- | 115377-36-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 苯甲醇,a-[(2E)-3,7-二甲基-2,6-辛二烯基]-
• 英文名称: (3E)-4,8-dimethyl-1-phenylnona-3,7-dien-1-ol
• CAS: 115377-36-1
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: WYINGXGTROQQGT-NTCAYCPXSA-N

物化性质

• 沸点：
  369.8±31.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  香叶醇 在 正丁基锂 、 三溴化磷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.58h， 生成 苯甲醇,a-[(2E)-3,7-二甲基-2,6-辛二烯基]-
  参考文献：
  名称：

  与受阻的亲核试剂和羰基亲电试剂锻造C–C键：烯丙基锡试剂/ n -BuLi的反应性和选择性

  摘要：

  根据与激活ñ-BuLi，含有巴豆基，香叶基和苯基二烯基甲基附件的三烷基锡烷与低反应性的各种酮和烯酮亲电试剂高效且选择性地反应。简单的过程使人们能够获得对季碳不利的叔醇。另一方面，用α，α′-二甲氧基-γ-吡喃酮进行二烯基侧链的接枝以立体和区域选择性和会聚的方式制备二烯基α′-甲氧基-γ-吡喃酮。此外，该路线的优势突出了在低温下制备有机锂物种并形成最少量的盐的优势。已证明合成操作说明了化学方法用于构建无环和环状萜烯支架的潜力。

  DOI：

  10.1021/acs.organomet.7b00765

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。
• Allylic Phosphates as Allyl Anion Synthons. Lithium-induced Allylation of Carbonyl Compounds
  作者：Shuki Araki、Yasuo Butsugan

  DOI：10.1246/cl.1988.457

  日期：1988.3.5

  Ultrasonication of allylic phosphates and carbonyl compounds with a lithium powder gave high yields of the corresponding homoallylic alcohols.

  使用锂粉超声处理烯丙基磷酸酯和羰基化合物，可以高产率地得到相应的高烯丙醇。
• 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).
• 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
• ARAKI, SHUKI;BUTSUGAN, YASUO, CHEM. LETT.,(1988) N 3, 457-458
  作者：ARAKI, SHUKI、BUTSUGAN, YASUO

  DOI：——

  日期：——