3-(1-hydroxy-1-methylethyl)indene | 64391-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-(1-hydroxy-1-methylethyl)indene
• 英文别名: 3-(2-hydroxypropan-2-yl)indene；2-inden-3-yl-propan-2-ol；1-(α-Oxy-isopropyl)-inden；2-Hydroxy-2--propan；3-(α-Hydroxyisopropyl)-inden；3-(2-Hydroxy-2-propyl)inden；2-(3H-inden-1-yl)propan-2-ol
• CAS: 64391-30-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: ACYYZOPRCUVBAR-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  297.1±9.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1-hydroxy-1-methylethyl)indene 在 盐酸 、 zinc(II) chloride 作用下， 生成 3-(2-chloropropan-2-yl)indene
  参考文献：
  名称：

  Leaving-group effects and ion-pair intermediates in base-promoted elimination competing with base-catalyzed 1,3-proton transfer

  摘要：

  DOI：

  10.1021/ja00466a028
• 作为产物：
  描述：

  2-hydroxyisopropylideneindan 生成 3-(1-hydroxy-1-methylethyl)indene
  参考文献：
  名称：

  THIBBLIN, A., J. CHEM. SOC. PERKIN TRANS., 1986, N 2, 313-319

  摘要：

  DOI：

文献信息

• Color Change of Disperse Dyes on Nylon 6 Films with Dye Concentration
  作者：Takashi Nakamura、Takao Shibusawa

  DOI：10.1177/004051750007000908

  日期：2000.9

  decreasing Cf. This result is consistent with the sorption behavior of these dyes by nylon 6 film from water, where the dyes are sorbed by the polymer as two distinct species: L—species—dye taken up by the polymer through the Langmuir sorption mechanism, and P—species—dye taken up by Nemst-type partitioning. For both dyes, the relations between C f and the concentrations of species I and II are very

  研究了分散染料在尼龙 6 薄膜上的光谱随染料浓度 ( Cf ) 降低的变化。大多数偶氮分散染料的可见光吸收最大值 (λmax) 会随着 C f 的降低而移向更长的波长。对于具有由分子内电荷转移引起的偶极结构的染料，这种转变是显着的。根据麦克雷方程和因子分析，详细分析了 CI 分散橙 3 和 5（实用分散染料）的光谱变化。在低 Cf 范围内，这些染料在胶片上的 λmax 值比 McRae 方程估计的波长长得多，并且随着温度的升高而转移到更短的波长。因子分析结果表明，随着 Cf 降低，染色薄膜的可见吸收光谱可以描述为两个不同光谱的总和，指定为物种 I 和 II。物种 I 在比物种 II 更长的波长处具有 λmax。[species I]/[species II] 的比率随着 C f 的减小而增加，导致 λmax 随着 Cf 的减小而发生红移。该结果与尼龙 6 薄膜对水中的这些染料的吸附行为一致
• Intra- and inter-molecular hydron abstraction from allylic carbocation intermediates in aqueous solvent. Observation of a substantial deuterium isotope effect for 1,4-elimination of acetic acid from one of the ion-pair intermediates
  作者：Alf Thibblin

  DOI：10.1039/p29860000321

  日期：——

  for production of (4). The kinetic deuterium isotope effect on hydron abstraction from the intermediate with acetate anion to form the olefin (3), (kH/kD) is 3.0 ± 0.4. The corresponding intramolecular elimination of acetic acid from the contact ion pair formed from 3-(2-acetoxypropan-2-yl)indene (1-OAc) to yield (3) shows a substantial isotope effect, kH/kD= 5.2 ± 1.0. The allylic isomer 2-acetoxy-1

  烯丙型碳正离子中间体，由3-（2-氯丙-2-基）茚（形成1 -Cl），并从（1,1- 2 ħ 2） - （1 35 -Cl）在75体积％的水-乙腈° C与溶剂水迅速反应，生成烯丙基醇，但也可通过一般的碱进行水合夺氢，生成1-异亚丙基茚（3）和3-异丙烯基茚（4）。发现用取代的乙酸根阴离子测量的布朗斯台德参数很小，对于（3）的形成，β为0.16，对于（4）的产生，为0.14 。氘的动力学同位素对中间体与乙酸根阴离子形成烯烃（3）的氢吸收的影响。），（k H / k D）为3.0±0.4。从3-（2-乙酰氧基丙烷-2-基）茚（1- OAc）形成的接触离子对中分子内乙酸的相应消除，产生（3），显示出相当大的同位素效应，k H / k D = 5.2± 1.0。烯丙基异构体2-乙酰氧基-1-异亚丙基（2 - OAc）产生接触离子对，其反应产生具有相当小的同位素效应的（3），k H / k D＝ 2
• Acid-catalysed intramolecular allylic rearrangement of methyl ethers in aqueous solvent. Evidence for the intermediacy of ion–molecule pairs in solvolysis
  作者：Alf Thibblin

  DOI：10.1039/p29870001629

  日期：——

  (2-OH) and (2-OMe). This seems to be the first demonstration of a carbocation-molecule pair as intermediate in a heterolytic reaction in a highly aqueous solvent. Analysis of the kinetic data, in combination with results obtained from solvolysis of the corresponding chloride 3-(1-chloro-1-methylethyl)indene (1-Cl), suggests that the intramolecular rearrangement of the ethers may in fact have two discrete

  2-甲氧基异亚丙基茚基（2-OMe）在9.1体积％乙腈的水溶液中进行酸催化的分子内烯丙基异构化反应，生成3-（1-甲氧基-1-甲基）乙基茚（1-OMe），并进行溶剂分解，生成3-（ 2-羟基-1-甲基乙基）茚（1-OH）和2-羟基-异亚丙基茚（2-OH）。异构化的速度比醇的生成慢11倍。醚（1-OMe）也溶剂化，但速度更慢，得到（1-OH）和痕量的（2-OH）和（2-OMe）。这似乎是碳正离子-分子对作为在高水溶剂中进行杂化反应的中间体的第一个证明。动力学数据分析，以及相应的氯化物3-（1-氯-1-甲基乙基）茚（1-Cl）的溶剂分解获得的结果，
• Courtot, Annales de Chimie (Cachan, France), 1915, vol. <9> 4, p. 205
  作者：Courtot

  DOI：——

  日期：——
• Synthesis and reactions of .alpha.-methylene-.beta.-keto sulfones
  作者：Andreas Weichert、H. Martin R. Hoffmann

  DOI：10.1021/jo00013a007

  日期：1991.6

  Modified Jones oxidation of 2-(benzenesulfonyl)-2-alken-1-ols and rapid nonnucleophilic workup below 0-degrees-C yields a variety of alpha-methylene-beta-keto sulfones 4, including crystalline parent 4a and also e-h, which can be stored at -20-degrees-C without change. In the absence of nucleophiles, the new compounds are stable (heating in benzene) toward dimerization and polymerization. Thus, selective cross-reactions are feasible. With alcohols, including sterically hindered tertiary alcohols and also with 2-(ethoxycarbonyl)cyclopentanone, the compounds function as efficient Micheal acceptors, even in the absence of base catalysis. In moist ether, 2-(benzenesulfonyl)-1-penten-3-one (4b) suffers rearrangement to 2-(benzenesulfonyl)ethyl propanoate (9). Sulfonylated alcohol 7 and strained alpha-hydroxyoxetane 8 are assumed as intermediates. Toward electron-rich aromatics and heteroaromatics, alpha-methylene-beta-keto sulfones 4 behave as electrophiles in Friedel-Crafts-type functionalizations. The new compounds are also dienophilic: of the two groups (acetyl and benzenesulfonyl) attached to the ethylenic terminus in 4a, benzenesulfonyl has been found to preferentially adopt the endo position in cycloadditions of cyclopentadiene and also cyclohexadiene. Prototype 3-(benzenesulfonyl)-3-buten-2-one (4a) is a crystalline methyl vinyl ketone (MVK) equivalent which, unlike MVK, undergoes controlled free-radical additions with nucleophilic radicals. In hetero-Diels-Alder reactions, 4a serves as a 1-oxa-1,3-butadiene unit, combining with a wide range of alkenes of graded nucleophilicity. Electron deficient 4a also reacts as an enophile toward 1,1-dialkylated ethylenes. In the presence of ZnCl2.OEt2, the ene reaction with beta-piene can be suppressed completely in favor of cycloaddition, giving a robustadial building block in 85% yield. In further applications to natural products chemistry, the synthesis of frontalin and novel oxatricyclics are described.