3-(3-tert-Butyl-phenoxy)-propane-1,2-diol | 55143-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-tert-Butyl-phenoxy)-propane-1,2-diol
• 英文别名: 3-(3-Tert-butylphenoxy)propane-1,2-diol
• CAS: 55143-04-9
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: DTQBBCXECKJBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-tert-Butyl-phenoxy)-propane-1,2-diol 在 ion-exchange resin Wofatit SBW (OH(-)-form) 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 100.0h， 生成 (2S)-3-(3-tert-butylphenoxy)propane-1,2-diol
  参考文献：
  名称：

  Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents

  摘要：

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.

  DOI：

  10.1021/jo00081a018
• 作为产物：
  描述：

  3-叔丁基苯酚 、 3-氯-1,2-丙二醇 生成 3-(3-tert-Butyl-phenoxy)-propane-1,2-diol
  参考文献：
  名称：

  Auzou; Rips; Derappe, European Journal of Medicinal Chemistry, 1974, vol. 9, # 5, p. 548 - 554

  摘要：

  DOI：

文献信息

• METHODS FOR HAIR FOLLICLE STEM CELL PROLIFERATION
  申请人：Frequency Therapeutics, Inc.

  公开号：US20200121681A1

  公开（公告）日：2020-04-23

  The present invention relates to compositions of minoxidil and Sonic Hedgehog (Shh) pathway activators and optionally, Wnt agonists and methods of using them to induce self-renewal of hair follicle stem cells, including inducing the hair follicle stem cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into hair follicle epithelial cells.

  本发明涉及米诺地尔和Sonic Hedgehog (Shh)途径激活剂以及可选的Wnt激动剂的组合物，以及使用它们诱导毛囊干细胞的自我更新的方法，包括诱导毛囊干细胞增殖，同时保持子细胞具有分化为毛囊上皮细胞的能力。
• 1H-pyrrole-2,5-dione compounds and methods of using same
  申请人：Frequency Therapeutics, Inc.

  公开号：US11066419B2

  公开（公告）日：2021-07-20

  The present invention relates to 1H-pyrrole-2,5-dione compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

  本发明涉及 1H-吡咯-2,5-二酮化合物和使用它们诱导干/祖支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时保持子细胞分化成组织细胞的能力。
• 1H-PYRROLE-2,5-DIONE COMPOUNDS AND METHODS OF USING THEM TO INDUCE SELF-RENEWAL OF STEM/PROGENITOR SUPPORTING CELLS
  申请人：Frequency Therapeutics, Inc.

  公开号：US20190352313A1

  公开（公告）日：2019-11-21

  The present invention relates to 1H-pyrrole-2,5-dione compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.
• US7557110B2
  申请人：——

  公开号：US7557110B2

  公开（公告）日：2009-07-07
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.