3,3-Dimethylnon-1-en-4-ol | 52922-12-0

• 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: 3,3-Dimethylnon-1-en-4-ol
• 英文别名: 3,3-dimethyl-1-nonen-4-ol；7,7-dimethylnon-8-en-6-ol；3,3-dimethyl-non-1-en-4-ol
• CAS: 52922-12-0
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: ZTAAATVTESKNGF-UHFFFAOYSA-N

物化性质

• 沸点：
  230.4±9.0 °C(Predicted)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  bromozinc(1+),2-methylbut-2-ene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 3,3-Dimethylnon-1-en-4-ol
  参考文献：
  名称：

  Propargyl and allyl Grignard and zinc reagents. Regioselective alkylation and its application to the synthesis of PGE3 and F3.alpha. methyl ester

  摘要：

  DOI：

  10.1021/jo00283a004

文献信息

• A highly efficient addition of allylic bromides to carbonyl compounds promoted by Cp2TiCl2(cat.)/Zn system
  作者：Yu Ding、Gang Zhao

  DOI：10.1016/s0040-4039(00)74734-4

  日期：1992.12

  Aldehydes or ketones reacted with allylic bromides in the presence of Cp2TiCl2(cat.)/Zn system at room temperature to give homo-allylic alcohols in high yields.

  在室温下，在Cp 2 TiCl 2（cat。）/ Zn体系存在下，醛或酮与烯丙基溴反应，以高收率得到均烯丙基醇。
• Synthesis of homoallylic (but-3-enylic) alcohols from aldehydes with allylic chlorides, tin(II) chloride and potassium iodide in water
  作者：Didier Houllemare、Francis Outurquin、Claude Paulmier

  DOI：10.1039/a608487g

  日期：——

  Homoallylic (but-3-enylic) alcohols have been prepared in good yields by reductive allylation of aldehydes in water with various allylic chlorides in the presence of tin(II) chloride and potassium iodide. The Barbier type reaction with prop-2-ynyl chloride is also achieved under the same conditions.

  烯丙型(丁-3-烯型)醇在高产率下通过醛在水相中的还原烯丙基化反应制备，其中使用不同烯丙型氯化物，并加入氯化锡(II)和碘化钾作为催化剂。同样条件下，利用丙-2-炔基氯化物也可以实现Barbier型反应。
• Regioselective allylation and propargylation using acylsilanes: facile synthesis of PGE3 and F3α methyl ester
  作者：Akira Yanagisawa、Shigeki Habaue、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)88868-2

  日期：1992.1

  Regioselective allylation and propargylation were achieved using acylsilanes as electrophiles and this methodology was applied to the synthesis of PGE3 and F3α methyl ester.

  区域选择性烯丙基炔丙基和使用acylsilanes作为亲电子实现，此方法适用于PGE的合成3和F 3α甲酯。
• The Reaction of some Carbonyl and Thiocarbonyl Compounds with Prenyl- and Crotyllithium in Tetrahydrofuran Solution
  作者：V. Rautenstrauch

  DOI：10.1002/hlca.19740570226

  日期：——

  (1) and cis-crotyllithium (Z-but-2-enyl-lithium) (2) in tetrahydrofuran solution, prepared according to the method of Eisch & Jacobs, react with carbonyl compounds to give the branched alcoholates with moderate to high selectivity, unless access to the carbonyl group is strongly hindered (see the Table). Adamantanethione (12) reacts with 1 to give the unbranched thiolate.

  按照Eisch＆Jacobs的方法制备的四氢呋喃溶液中的异戊烯基锂（3-甲基丁-2-烯基锂）（1）和顺丁烯基锂（Z-丁-2-烯基锂）（2）与羰基反应除非强烈阻碍了羰基的进入，否则这些化合物会以中等至高的选择性生成支链醇化物。金刚烷硫酮（12）与1反应生成未支化的硫醇盐。
• A Highly Atom Efficient, Solvent Promoted Addition of Tetraallylic, Tetraallenic, and Tetrapropargylic Stannanes to Carbonyl Compounds
  作者：Adam McCluskey、I. Wayan Muderawan、Muntari、David J. Young

  DOI：10.1021/jo015904x

  日期：2001.11.1

  Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation. reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.