2-ethyl-1-(2-hydroxymethylphenyl)-2-butanol | 164731-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethyl-1-(2-hydroxymethylphenyl)-2-butanol
• 英文别名: 2-ethyl-1-(2-hydroxymethylphenyl)butan-2-ol；3-[[2-(Hydroxymethyl)phenyl]methyl]pentan-3-ol
• CAS: 164731-36-6
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: JTSNOPVILYOUGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-(2-hydroxymethylphenyl)-2-butanol 在 磷酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以83%的产率得到3,3-diethyl-3,4-dihydro-1H-2-benzopyran
  参考文献：
  名称：

  1,2-Di(lithiomethyl)benzene from phthalan: Sequential introduction of two different electrophiles

  摘要：

  The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20 degrees C followed by treatment with electrophiles (D2O, CO;! and carbonyl compounds) at -78 degrees C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g. When the Lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added the corresponding disubstituted compounds 6a-q are prepared. Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k), respectively. Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.

  DOI：

  10.1016/0040-4020(95)00064-f
• 作为产物：
  描述：

  7,7-diethyl-5,9-dihydro-6,8-dioxabenzenecycloheptene 在 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以40%的产率得到2-ethyl-1-(2-hydroxymethylphenyl)-2-butanol
  参考文献：
  名称：

  Garcia, Daniel; Foubelo, Francisco; Yus, Miguel, Heterocycles, 2007, vol. 74, # C, p. 507 - 519

  摘要：

  DOI：

文献信息

• Reductive Ring Opening of Oxygen-Containing Benzo-Fused Heterocycles by an Arene-Catalysed Lithiation
  作者：Miguel Yus、Benjamín Moreno、Francisco Foubelo

  DOI：10.1055/s-2004-815971

  日期：——

  The reductive ring opening of phthalan and isochroman in a 8 mmol scale process, using a small excess of lithium (1.35 equiv) and a substoichiometric amount of DTBB (3 mol%), leads to functionalised organolithium compounds, which after reaction with (-)-menthone as electrophile followed by hydrolysis with water, gives the corresponding diols in good yields with high stereoselectivity. Dehydration of these diols leads to the corresponding oxygen-containing heterocycles, which are homologous of the starting heterocycles.

  使用过量的锂（1.35当量）和次化学计量的二叔丁基二硫（3摩尔%），在8毫摩尔规模下进行酞喃和异色满的还原开环反应，得到功能化的有机锂化合物。通过与(-)-薄荷酮作为亲电试剂反应，然后用水进行水解，可以高产率、高立体选择性地获得相应的二醇。这些二醇的脱水反应生成含氧杂环，它们是起始杂环的同系物。
• Functionalised organotitanium compounds: from lithium to titanium intermediates in chemoselective reactions with carbonyl compounds
  作者：Isidro M Pastor、Miguel Yus

  DOI：10.1016/s0040-4020(01)00103-x

  日期：2001.3

  The reaction of functionalised organolithium compounds 1 with an equimolecular mixture of two carbonyl compounds in the presence of 2 equiv. of triisopropoxytitanium chloride can discriminate between aldehyde and ketone, the process being selective for aldehydes at room temperature. Electronic and steric effects have been observed for different aldehydes.

  在2当量存在下，官能化的有机锂化合物1与两种羰基化合物的等分子混合物的反应。氯化三异丙氧基钛可以区分醛和酮，该方法在室温下对醛具有选择性。对于不同的醛，已经观察到电子和空间效应。
• Lithiation Reactions Catalyzed by Linear and Cross-Linked Arene-Based Polymers. Generation of Functionalized Organolithium Compounds
  作者：P. Candela、C. Gómez、M. Yus

  DOI：10.1023/b:rujo.0000044541.84132.e5

  日期：2004.6

  Lithiation of various substrates, such as chlorinated acetals, alpha-chloro ether, dichloro derivatives, benzo-fused heterocycles, and allyl and benzyl derivatives, with excess lithium powder in the presence of a catalytic amount of soluble linear or insoluble cross-linked arene (naphthalene or biphenyl)-based polymers yields the expected organolithium intermediates. The latter react with electrophiles either in two steps or under Barbier-type reaction conditions to afford the corresponding adducts. The catalyst is easily recuperated by filtration at the end of the process, and the procedure can be regarded as a reasonable alternative to the use of free arenes as electron carrier in lithiation reactions.
• Polyphenylene as an electron transfer catalyst in lithiation processes
  作者：Miguel Yus、Cecilia Gómez、Pablo Candela

  DOI：10.1016/s0040-4020(02)00620-8

  日期：2002.7

  The lithiation of different functionalised chlorinated materials (1a-c), dichlorinated compounds (1d-f) and benzofused cyclic ethers (1g,h) with lithium powder in the presence of catalytic amounts of either linear (LPP) or crosslinked (CPP) polyphenylene, in THF at temperatures ranging between -78 and 20degreesC, leads to the expected organolithium intermediates (1a-h), which by reaction with electrophiles [(BuCHO)-C-t, PhCHO, Et2CO, (CH2)(5)CO, PhCOMe, Me3SiCl] gives, after hydrolysis with water, the expected products 2aa-hf. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 1,2-Di(lithiomethyl)benzene from phthalan: Sequential introduction of two different electrophiles
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1016/0040-4020(95)00064-f

  日期：1995.3

  The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20 degrees C followed by treatment with electrophiles (D2O, CO;! and carbonyl compounds) at -78 degrees C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g. When the Lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added the corresponding disubstituted compounds 6a-q are prepared. Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k), respectively. Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.