2-(4-叔丁基苄基)-1,3-丙二醇 | 172477-52-0

• 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: 2-(4-叔丁基苄基)-1,3-丙二醇
• 英文名称: 2-(4-tert-butylbenzyl)-1,3-propanediol
• 英文别名: 2-(4-t-butylbenzyl)-1,3-propanediol；2-(4-t-Butylbenzyl)-1,3-propandiol；2-[(4-tert-butylphenyl)methyl]propane-1,3-diol
• CAS: 172477-52-0
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: ASVJAMMASGZXCV-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±27.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-(4-叔丁基苄基)-1,3-丙二醇 在 氯化亚砜 、 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 0.17h， 生成 1-叔丁基-4-(环丙基甲基)苯
  参考文献：
  名称：

  由1,3-二醇通过相应的环状硫酸盐合成取代的环丙烷

  摘要：

  不同环硫酸酯的反应2（从相应的1,3-二醇容易地制备1以下的夏普勒斯方法）与过量的锂粉末和DTBB（5摩尔％）引线的催化量的相应的取代的环丙烷3通过γ消除过程中，硫酸根离子充当离去基团。

  DOI：

  10.1016/0040-4020(95)00708-g
• 作为产物：
  描述：

  diethyl 4-t-butylbenzylmalonate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到2-(4-叔丁基苄基)-1,3-丙二醇
  参考文献：
  名称：

  由1,3-二醇通过相应的环状硫酸盐合成取代的环丙烷

  摘要：

  不同环硫酸酯的反应2（从相应的1,3-二醇容易地制备1以下的夏普勒斯方法）与过量的锂粉末和DTBB（5摩尔％）引线的催化量的相应的取代的环丙烷3通过γ消除过程中，硫酸根离子充当离去基团。

  DOI：

  10.1016/0040-4020(95)00708-g

文献信息

• Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph
  作者：Amir Avdagić、Mirjana Gelo-Pujić、Vitomir Šunjić

  DOI：10.1055/s-1995-4107

  日期：1995.11

  Chemoenzymatic synthesis of the S-(-)-enantiomer of fenpropimorph (S)-1 in high optical and chemical purity is described. One feature of this process entails the enantioselective acetylation of prochiral 1,3-propanediol 4 by Pseudomonas sp. lipases, and subsequent transformation of the monoacetate (R)-5 into the final product by the selected order of transformations that comprise; chlorination or tosylation under non-racemizing conditions, hydrogenolysis of the resulting chloromethyl or tosyl group in (+)-6 and (+)-8, second chlorination of (-)-9, and alkylation of cis-3,5-dimethylmorpholine by 1-chloropropane derivative (+)-10. This sequence of reactions affords (S)-1, the more active enantiomer in the commercialized racemic mixture with systemic fungicidal activity.

  本研究介绍了高光学纯度和化学纯度的芬普吗啉（S）-1 的 S-(-)-对映体的化学合成。该工艺的一个特点是通过假单胞菌（Pseudomonas sp.该工艺的特点之一是利用假单胞菌脂肪酶对 1,3-丙二醇 4 的手性进行对映体选择性乙酰化，然后通过选定的转化顺序将单乙酸酯 (R)-5 转化为最终产品，这些转化顺序包括：在非梯度化条件下进行氯化或甲苯磺酰化反应，对 (+)-6 和 (+)-8 中产生的氯甲基或甲苯磺酰基进行氢解反应，对 (-)-9 进行第二次氯化反应，以及用 1-氯丙烷衍生物 (+)-10 对顺式-3,5-二甲基吗啉进行烷基化反应。通过这一系列反应，可得到(S)-1，它是商品化外消旋混合物中活性更强的对映体，具有系统杀菌活性。
• VANILLOID ANALOGUES CONTAINING RESINIFERATOXIN PHARMACOPHORES AS POTENT VANILLOID RECEPTOR AGONISTS AND ANALGESICS, COMPOSITIONS AND USES THEREOF
  申请人：PACIFIC CORPORATION

  公开号：EP1154989B1

  公开（公告）日：2005-12-14
• US6476076B1
  申请人：——

  公开号：US6476076B1

  公开（公告）日：2002-11-05
• [EN] VANILLOID ANALOGUES CONTAINING RESINIFERATOXIN PHARMACOPHORES AS POTENT VANILLOID RECEPTOR AGONISTS AND ANALGESICS, COMPOSITIONS AND USES THEREOF<br/>[FR] ANALOGUES DE VANILLOIDE CONTENANT DES PHARMACOPHORES DE RESINIFERATOXINE, UTILISES EN TANT QU'AGONISTES DU RECEPTEUR DE VANILLOIDE ET ANALGESIQUES PUISSANTS, COMPOSITIONS ET LEURS UTILISATIONS
  申请人：PACIFIC CORP

  公开号：WO2000050387A1

  公开（公告）日：2000-08-31

  The present invention is related to new vanilloid analogues containing resiniferatoxin pharmacophores, pharmaceutical compositions comprising such analogues, and their uses as vanilloid receptor agonists and potent analgesics. The present invention provides a pharmaceutical composition for treating acute, chronic, inflammatory or neuropathic pains or for treating bladder hypersensitivity.
• N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives as potent vanilloid receptor agonists and analgesics
  作者：Jeewoo Lee、Jiyoun Lee、Jiyoung Kim、Soo Yeon Kim、Moon Woo Chun、Hawon Cho、Sun Wook Hwang、Uhtaek Oh、Young Ho Park、Victor E Marquez、Maryam Beheshti、Tamas Szabo、Peter M Blumberg

  DOI：10.1016/s0968-0896(00)00216-9

  日期：2001.1

  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.