(2,3-dihydro-1H-indene-2,2-diyl)dimethanol | 82044-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2,3-dihydro-1H-indene-2,2-diyl)dimethanol
• 英文别名: β.β-Bis-oxymethyl-hydrinden；2,2-Bis-hydroxymethyl-indan；2.2-Bis-oxymethyl-hydrinden；[2-(Hydroxymethyl)-1,3-dihydroinden-2-yl]methanol
• CAS: 82044-46-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: XPWNCSMIBZZLFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  112.5 °C
• 沸点：
  200 °C(Press: 3 Torr)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (2,3-dihydro-1H-indene-2,2-diyl)dimethanol 在 镍 吡啶 、 氨 、 氢气 、 sodium hydride 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 spiro[(1-aminocyclobutane)-3:2'-indan]-1-methylamine
  参考文献：
  名称：

  潜在的抗抑郁药显示组合的alpha（2）-肾上腺素受体拮抗剂和单胺摄取抑制剂的性质。

  摘要：

  人们认为经典的抗抑郁药通过提高大脑中的单胺（5-羟色胺和去甲肾上腺素）水平来发挥作用。通常通过抑制单胺代谢（MAO抑制剂）或阻断单胺摄取（三环类抗抑郁药和选择性5-羟色胺或去甲肾上腺素再摄取抑制剂）来完成该作用。但是，所有此类药物均存在时滞（3--6周），才能证明其强大的临床功效。此延迟可能反映了去甲肾上腺素对突触前α（2A）-肾上腺素能自发或异源受体的抑制作用，该抑制作用在长时间暴露下会逐渐下调。具有单胺摄取抑制特性的拮抗剂对突触前α（2A）-肾上腺素受体的阻断作用可能导致新的抗抑郁药具有更高的疗效和更短的时间延迟。在文献中 仅描述了两个具有这种药理学特征的分子。其中，萘哌唑（2）被选为设计4（5）-[（（3,4-二氢-2-萘基）甲基] -4,5-二氢咪唑（4a）的起点。所需的配置文件：α（2A）-肾上腺素受体拮抗剂特性和5-羟色胺/去甲肾上腺素摄取抑制。从这个原始分子，设计并合成了一系

  DOI：

  10.1021/jm001040g
• 作为产物：
  描述：

  邻二氯苄 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2,3-dihydro-1H-indene-2,2-diyl)dimethanol
  参考文献：
  名称：

  N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives as potent vanilloid receptor agonists and analgesics

  摘要：

  A series of N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl)thioura derivatives were investigated as vanilloid receptor ligands in an effort to discover a novel class of analgesics. The proposed pharmacophore model of resiniferatoxin, which includes the C-20-homovanillic moiety, the C-3-carbonyl and the orthoester phenyl ring as key pharmacophoric groups, was utilized as a guide for drug design. The compounds were synthesized after several steps from diethylmalonate and evaluated in vitro in a receptor binding assay and in a capsaicin-activated channel assay. Additional evaluation of analgesic activity, anti-inflammatory activity and pungency was conducted in animal models by the writhing test, the ear edema assay, and the eye-wiping test, respectively. Among the new compounds, 23 and 28 were found to be the most potent receptor agonists of the series with K-i values of 19 nM and 11 nM, respectively. Their strong in vitro potencies were also reflected by an excellent analgesic profile in animal tests with ED50 values of 0.5 mug/kg for 23 and 1.0 mug/kg for 28. Relative to capsaicin these compounds appear to be ca. 600 and 300 times more potent. Both 23 and 28 were found to be less pungent than capsaicin based on the eye-wiping test. However, the compounds did not show significant anti-inflammatory activity. A molecular modeling study comparing the energy-minimized structures of resiniferatoxin and 35 demonstrated a good correlation in the spatial disposition of the corresponding key pharmacophores. The thioureas described in this investigation, which were designed as simplified resiniferatoxin surrogates, represent a novel class of potent vanilloid receptor agonists endowed with potent analgesic activity and reduced pungency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00216-9

文献信息

• Highly Stereoselective Synthesis of Fused Tetrahydropyrans via Lewis-Acid-Promoted Double C(sp³)–H Bond Functionalization
  作者：Kazuma Yokoo、Dan Sakai、Keiji Mori

  DOI：10.1021/acs.orglett.0c01867

  日期：2020.8.7

  functionalization at a position adjacent to an oxygen atom and a benzylic/aliphatic position through the employment of substrates with a dialkyl group in the alkyl chain, which enabled the highly diastereoselective synthesis of fused tetrahydropyrans.

  通过使用烷基链中带有二烷基的底物，我们在邻近氧原子的位置和苄基/脂肪族位置实现了氢化物移位触发的双C（sp 3）-H双键连续官能化高度融合的四氢吡喃非对映选择性合成。
• Solid-Supported [2+2+2] Cyclotrimerizations
  作者：Douglas D. Young、Ramesh S. Senaiar、Alexander Deiters

  DOI：10.1002/chem.200501360

  日期：2006.7.17

  The transition-metal-catalyzed [2+2+2] cyclotrimerization of a diyne and an alkyne provides a convergent route to highly-substituted aromatic rings. This reaction possesses distinct drawbacks, especially low chemo- and regioselectivities, which hamper its application in combinatorial synthesis. These problems have been solved by the development of solid-supported [2+2+2]-cycloaddition reactions. If conducted

  二炔和炔烃的过渡金属催化的[2 + 2 + 2]环三聚反应提供了一条通往高度取代的芳环的会聚路线。该反应具有明显的缺点，特别是低的化学选择性和区域选择性，这阻碍了其在组合合成中的应用。通过开发固相支持的[2 + 2 + 2]-环加成反应已解决了这些问题。如果在固体载体上进行，则该反应能够快速组合获得碳和杂环小分子阵列的不同集合。通过检查不同的固定化策略，不同的二炔前体和各种功能化的炔反应伙伴，研究了该方法的范围。总体而言，异吲哚啉，邻苯二甲酸酯和茚满文库的组装效率很高，纯度很高，纯度很高。
• Electroorganic chemistry. Part 58. New synthesis of cyclopropanes from 1,3-dicarbonyl compounds utilizing electroreduction of 1,3-dimethanesulfonates
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata、Yoshihiro Sugihara

  DOI：10.1021/jo00137a012

  日期：1982.7
• Kenner, Journal of the Chemical Society, 1914, vol. 105, p. 2694
  作者：Kenner

  DOI：——

  日期：——