1-(2-羟甲基苯基)-3,3-二甲基-2-丁醇 | 164731-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-羟甲基苯基)-3,3-二甲基-2-丁醇
• 英文名称: 1-(2-hydroxymethylphenyl)-3,3-dimethyl-2-butanol
• 英文别名: 3,3-Dimethyl-1-(2-methylolphenyl)butan-2-ol；1-[2-(hydroxymethyl)phenyl]-3,3-dimethylbutan-2-ol
• CAS: 164731-35-5
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: VKOINQVBHMMHEI-UHFFFAOYSA-N

物化性质

• 沸点：
  332.1±22.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 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：

  1-(2-羟甲基苯基)-3,3-二甲基-2-丁醇 在 磷酸 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到3,4-dihydro-3-(1,1-dimethylethyl)-1H-2-benzopyran
  参考文献：
  名称：

  邻苯二酚的还原亲电取代和扩环成异色满衍生物

  摘要：

  在催化量的萘的存在下，邻苯二甲酸1a与锂金属的还原裂解导致形成稳定的芳族二锂化合物。后者与CO 2，醛或酮的加成物闭环成异色满衍生物，导致原始杂环的扩环。还原亲电取代程序已成功地扩展到取代的酞菁1b和1c，以令人满意的产率提供了相应的异色满-3one。

  DOI：

  10.1016/0040-4039(95)01692-b
• 作为产物：
  描述：

  1,3-二氢异苯并呋喃 、 特戊醛 在 萘 、 lithium 作用下， 生成 1-(2-羟甲基苯基)-3,3-二甲基-2-丁醇
  参考文献：
  名称：

  邻苯二酚的还原亲电取代和扩环成异色满衍生物

  摘要：

  在催化量的萘的存在下，邻苯二甲酸1a与锂金属的还原裂解导致形成稳定的芳族二锂化合物。后者与CO 2，醛或酮的加成物闭环成异色满衍生物，导致原始杂环的扩环。还原亲电取代程序已成功地扩展到取代的酞菁1b和1c，以令人满意的产率提供了相应的异色满-3one。

  DOI：

  10.1016/0040-4039(95)01692-b

文献信息

• Reductive electrophilic substitution of phthalans and ring expansion to isochroman derivatives
  作者：Ugo Azzena、Salvatore Demartis、Maria Giovanna Fiori、Giovanni Melloni、Luisa Pisano

  DOI：10.1016/0040-4039(95)01692-b

  日期：1995.10

  of a stable aromatic dilithium compound. The adducts of the latter with CO2, aldehydes or ketones undergo ring closure to isochroman derivatives, leading to ring expansion of the original heterocycle. The reductive electrophilic substitution procedure was successfully extended to the substituted phthalans 1b and 1c, to afford the corresponding isochroman-3ones in satisfactory yields.

  在催化量的萘的存在下，邻苯二甲酸1a与锂金属的还原裂解导致形成稳定的芳族二锂化合物。后者与CO 2，醛或酮的加成物闭环成异色满衍生物，导致原始杂环的扩环。还原亲电取代程序已成功地扩展到取代的酞菁1b和1c，以令人满意的产率提供了相应的异色满-3one。
• 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。
• 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.
• 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.
• Electron-Transfer-Induced Reductive Cleavage of Phthalans:  Reactivity and Synthetic Applications
  作者：Ugo Azzena、Salvatore Demartis、Giovanni Melloni

  DOI：10.1021/jo9604548

  日期：1996.1.1

  The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed.