3-(2-hydroxyphenyl)propane-1,2-diol | 24454-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(2-hydroxyphenyl)propane-1,2-diol
• 英文别名: 1-(2-Hydroxy-phenyl)-propandiol-(2,3)；1-(o-Hydroxyphenyl)propan-2,3-diol；3-o-Hydroxyphenylpropan-1,2-diol；2(2',3'-Dihydroxypropyl)phenol；3-(2-Hydroxyphenyl)propane-1,2-diol
• CAS: 24454-25-9
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: LEVOMOZAZKPWJU-UHFFFAOYSA-N

物化性质

• 沸点：
  175 °C(Press: 1.2 Torr)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyphenyl)propane-1,2-diol 在 过碘酸 作用下， 生成 2-羟基苯基乙醛
  参考文献：
  名称：

  醌的光诱导反应和相关反应。第六部分 一些带有甲酰基的对苯醌的反应

  摘要：

  甲酰基-1,4-苯醌，1,4-苯醌基乙醛，3-（1,4-苯醌基）丙醛，2-（1,4-苯醌基）-2-甲基丙醛和2-甲基-2-（1）的制备描述了（4-萘醌-2-基）丙醛。用可见光照射这些苯醌在苯中的溶液导致将2，5-二羟基苯甲酸从甲酰基-1，4-苯醌中分离出来，并形成5-羟基香豆素-2-酮和3,4-二氢-接下来的两个醌中的6-羟基香豆素；该系列中的最后两个醌失去甲醛元素，分别生成5-羟基-3-甲基苯并呋喃和5-羟基-3-甲基萘-[1,2- b ]呋喃。没有任何辐射进行得很干净。

  DOI：

  10.1039/j39700000649
• 作为产物：
  描述：

  2-烯丙基酚 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 为溶剂， 以99%的产率得到3-(2-hydroxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  1,2,n-三醇的一锅区域和立体选择性环化

  摘要：

  提出了一种简单有效的方法来环化含有 1,2-二醇官能团和侧羟基的三醇。一锅法将 1,2-二醇原位转化为原酸酯，在用路易斯酸处理后生成环状丙酮鎓中间体。该中间体随后被侧羟基捕获以生成环醚。1,2-二醇的立体化学完全保真（在环化位点反转）转移到产物中，反应以高区域选择性进行。该过程类似于路易斯酸催化的带有羟基的环氧化物分子内开环，产生具有区域和立体化学控制的各种尺寸的环醚。

  DOI：

  10.1021/ja043002i

文献信息

• One-Pot Regio- and Stereoselective Cyclization of 1,2,<i>n</i>-Triols
  作者：Tao Zheng、Radha S. Narayan、Jennifer M. Schomaker、Babak Borhan

  DOI：10.1021/ja043002i

  日期：2005.5.1

  A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry

  提出了一种简单有效的方法来环化含有 1,2-二醇官能团和侧羟基的三醇。一锅法将 1,2-二醇原位转化为原酸酯，在用路易斯酸处理后生成环状丙酮鎓中间体。该中间体随后被侧羟基捕获以生成环醚。1,2-二醇的立体化学完全保真（在环化位点反转）转移到产物中，反应以高区域选择性进行。该过程类似于路易斯酸催化的带有羟基的环氧化物分子内开环，产生具有区域和立体化学控制的各种尺寸的环醚。
• Acid cosmetic, dermatological and pharmaceutical agents
  申请人：——

  公开号：US20040115148A1

  公开（公告）日：2004-06-17

  The invention provides acidic cosmetic, pharmaceutical and dermatological agents comprising at least one copolymer obtainable by free-radical copolymerization of A) acryloyld imethyltaurine and/or acryloyldimethyltaurates, B) if desired, one or more further olefinically unsaturated, noncationic comonomers, C) if desired, one or more olefinically unsaturated, cationic comonomers, D) if desired, one or more silicon-containing components, E) if desired, one or more fluorine-containing components, F) if desired, one or more macromonomers, G) the copolymerization taking place if desired in the presence of at least one polymeric additive, H) with the proviso that component A) is copolymerized with at least one component selected from one of the groups D) to G).

  本发明提供了酸性化妆品、药物和皮肤剂，其中包含至少一种共聚物，该共聚物可通过以下物质的自由基共聚得到 A) 丙烯酸二甲基脲和/或丙烯酰二甲基脲酸酯、 B) 如果需要，再加入一种或多种烯烃不饱和非阳离子共聚单体、 C) 如果需要，一种或多种烯烃不饱和阳离子共聚单体、 D) 如果需要，一种或多种含硅成分、 E) 如果需要，一种或多种含氟成分、 F) 如果需要，一种或多种大单体、 G) 如果需要，在至少一种聚合物添加剂的存在下进行共聚、 H) 条件是成分 A) 与选自 D) 至 G) 组中的至少一种成分共聚。
• Selective Inhibition of ICAM-1 and E-Selectin Expression in Human Endothelial Cells. 2. Aryl Modifications of 4-(Aryloxy)thieno[2,3-<i>c</i>]pyridines with Fine-Tuning at C-2 Carbamides
  作者：Gui-Dong Zhu、David L. Arendsen、Indrani W. Gunawardana、Steven A. Boyd、Andrew O. Stewart、Dennis G. Fry、Barbara L. Cool、Lemma Kifle、Verlyn Schaefer、Joseph Meuth、Kennan C. Marsh、Anita J. Kempf-Grote、Patrick Kilgannon、W. Michael Gallatin、Gregory F. Okasinski

  DOI：10.1021/jm0101702

  日期：2001.10.1

  The elevated expression of cell adhesion molecules (CAMs) on the lumenal surface of vascular endothelial cells is a critical early event in the complex inflammatory process. The adhesive interactions of these CAMs that include E-selectin, ICAM-1, and VCAM-1 with their counterreceptors on leukocytes, such as integrins of the alpha (L)beta (2) family, result in migration of the leukocytes to the site of inflammation and cause tissue injury. Pharmaceutical agents that could suppress the induced expression of one or more of these cell adhesion molecules would provide a novel mechanism to attenuate the inflammatory responses associated with chronic inflammatory diseases. A-205804 (1), a potent and selective inhibitor of the induced expression of E-selectin and ICAM-1 over VCAM-1, was further modified with emphasis at the C-4 and C-2 positions to identify a more potent drug candidate with a good pharmacokinetic profile and physical properties. Replacement of the C-4 sulfur linkage in I with an oxygen atom eliminated one of the two major metabolites for this lead molecule. The para-position of the 4-phenoxy group of the thieno[2,3-c]pyridine lead is found to be very critical for a higher in vitro potency and selectivity of E-selectin and ICAM-1 over VCAM-1 expression. This position is presumably close to the solvent-accessible region of the target protein-inhibitor complex. An attempt to install a water-solubilizing group at the para-position of the phenoxy group to increase the aqueous solubility of this lead series through various linkages failed to provide an ideal inhibitor. Only small substituents such as fluorine are tolerated at the meta- and ortho-positions of the 4-phenoxy to retain a good in vitro potency. Bromo, trifluoromethyl, pyrazol-1-yl, and imidazol-1-yl are among the better substituents at the para-position. With fine-tuning at the C-2 position we discovered a series of very potent (IC50 < 5 nM for ICAM-1) and selective (> 200-fold vs VCAM-1) inhibitors with a good pharmacokinetic profile. Demonstrated efficacy in a rat rheumatoid arthritis model and in a mice asthma model with selected compounds is also reported.
• A PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF SEBORRHEA CONTAINING 4-HYDROXY-5-METHOXY-4- 2-METHYL-3(3-METHYL-2-BUTENYL)-2-OXIRANYL]-1-OXASPIRO 2,5]OCTAN-6-ONE
  申请人：Mycoplus Co., Ltd.

  公开号：EP1509220A1

  公开（公告）日：2005-03-02
• EP1509220A4
  申请人：——

  公开号：EP1509220A4

  公开（公告）日：2009-04-01