Methyl 3-hydroxy-3-methyl-5-hexenoate | 89358-08-7

• 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: Methyl 3-hydroxy-3-methyl-5-hexenoate
• 英文别名: methyl 3-hydroxy-3-methyl-5-hexanoate；methyl 3-hydroxy-3-methylhex-5-enoate；5-Hexenoic acid, 3-hydroxy-3-methyl-, methyl ester
• CAS: 89358-08-7
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: DREBSVIUEKZLNA-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±28.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-hydroxy-3-methyl-5-hexenoate 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到<1-2H2>-3-methylhex-5-ene-1,3-diol
  参考文献：
  名称：

  Ferraboschi, Patrizia; Canevotti, Renato; Grisenti, Paride, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2301 - 2304

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二烯丙基乙醇 在 sodium hydroxide 、 臭氧 、 silver nitrate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 4.08h， 生成 Methyl 3-hydroxy-3-methyl-5-hexenoate
  参考文献：
  名称：

  Ferraboschi, Patrizia; Canevotti, Renato; Grisenti, Paride, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2301 - 2304

  摘要：

  DOI：

文献信息

• Facile Preparation of Allylzinc Species from Allyl Bromides and Unactivated Zinc Induced by a Catalytic Amount of Aluminum Chloride and Their Reactions with Carbonyl Compounds and Acetals.
  作者：Hatsuo MAEDA、Kazushige SHONO、Hidenobu OHMORI

  DOI：10.1248/cpb.42.1808

  日期：——

  The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3, was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α, β-unsaturated carbonyl compounds, selective 1, 2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavege also proceeded in excellent yields provided that two equivalents of AlCl3 was present.

  在干燥的四氢呋喃（THF）中，研究了路易斯酸（ZnCl2、AlCl3、BF3和TiCl4）对烯丙基溴和未活化的锌粉生成烯丙基锌物种的影响，并通过苯甲醛捕获有机锌化合物，即醛的格氏型烯丙基化反应。在所用的路易斯酸中，AlCl3被发现是最优的促进剂。在催化量的AlCl3存在下预形成的烯丙基锌物种能有效地烯丙基化羰基化合物。各种芳香族和脂肪族醛以及酮被转化为同烯丙基醇，产率良好至优秀。在所采用的反应条件下，酯、羟基、缩醛以及芳香族硝基和卤素基团均被容忍。对于α,β-不饱和羰基化合物，观察到了选择性的1,2-加成。取代的烯丙基溴如香叶基、巴豆基、肉桂基和2-环己烯基溴均能顺利转化为相应的烯丙基锌化合物，这些化合物与羰基化合物反应生成取代的同烯丙基醇，产率极佳。在巴豆基化、肉桂基化和2-环己烯基化中的立体选择性取决于有机金属和亲电试剂的结构。讨论了观察到的选择性的起源。在AlCl3的两当量存在下，伴随着碳-氧键断裂的二甲基和环状缩醛的烯丙基化也以极佳的产率进行。
• Grignard-type allylation of carbonyl compounds in methanol by the electrochemically recycled allyltin reagent.
  作者：Kenji Uneyama、Hiroyuki Matsuda、Sigeru Torii

  DOI：10.1016/s0040-4039(01)81748-2

  日期：——

  An electrochemical allylation of aldehydes and ketones in methanol was achieved by the electroreductive regeneration of diallyltin reagent in the presence of a catalytic amount of tin, affording the corresponding homoallyl alcohols in 72 – 91% yields.

  在催化量的锡存在下，通过对二烯丙基化试剂进行电还原再生，实现了甲醇中醛和酮的电化学烯丙基化，从而以72 – 91％的产率提供了相应的均烯丙基醇。
• Novel and Efficient Method for the Allylation of Carbonyl Compounds and Imines Using Triallylaluminum
  作者：Kao-Hsien Shen、Ching-Fa Yao

  DOI：10.1021/jo052385f

  日期：2006.5.1

  triallylaluminum as a reagent for the allylation of carbonyl compounds and imines. The allylation of ketimines without additional metal catalyst is known so far only in the case of the Grignard reagent. Triallylaluminum is a useful alternative to provide the homoallylic amines in excellent yield upon addition to aldimines and ketimines. The significant reactivity of this reagent was confirmed by its

  这是首次使用三烯丙基铝作为羰基化合物和亚胺的烯丙基化试剂的报道。迄今仅在格氏试剂的情况下才知道没有附加金属催化剂的酮亚胺的烯丙基化。三烯丙基铝是添加到醛亚胺和酮亚胺中后以优异产率提供均烯丙基胺的有用替代品。该试剂与空间刚性的酮（如金刚烷酮）反应，以98％的收率提供1-金刚烷基-3-丁烯-1-醇，证实了该试剂的显着反应性。通过使用不同的酮酸酯证明了三烯丙基铝的化学选择性。值得注意的是，三烯丙基铝是由烯丙基溴和铝金属而不是格氏试剂制得的，并且该过程操作简单，从而导致了良好的产品收率。
• Barluenga, Jose; Florez, Josefa; Yus, Miguel, Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 3019 - 3026
  作者：Barluenga, Jose、Florez, Josefa、Yus, Miguel

  DOI：——

  日期：——
• Enantioselective hydrolysis of 3-hydroxy-3-methylalkanoic acid esters with pig liver esterase
  作者：William K. Wilson、Shawn B. Baca、Yolanda J. Barber、Terence J. Scallen、Cary J. Morrow

  DOI：10.1021/jo00170a017

  日期：1983.11