(R)-2-(p-tolyl)propane-1,2-diol | 127393-68-4

• 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: (R)-2-(p-tolyl)propane-1,2-diol
• 英文别名: 2-(p-tolyl)propane-1,2-diol；2-p-tolylpropane-1,2-diol；(2R)-2-(4-methylphenyl)propane-1,2-diol
• CAS: 127393-68-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JVSJDMWWPVKLEI-JTQLQIEISA-N

物化性质

• 沸点：
  317.7±27.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (R)-2-(p-tolyl)propane-1,2-diol 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 6.0h， 以72%的产率得到(R)-2-p-tolylpropan-1-ol
  参考文献：
  名称：

  Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach

  摘要：

  The enantioselective synthesis of both isomers of ar-himachalene has been achieved starting from enantiomerically pure citronellal and p-methyl alpha-methyl styrene as an application of a chiral pool and chirality induction approach, respectively. The key reactions involved in the synthesis include the Sharpless asymmetric dihydroxylation for the induction of chirality at benzylic carbon bearing the methyl group and the use of a hypervalent iodine reagent or trimethylsilyldiazomethane (TMSCHN2) for the six to seven membered ring expansion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.008
• 作为产物：
  描述：

  2-(对甲苯基)丙醛 在 sodium tetrahydroborate 、 N-(4-nitrobenzenesulfonyl)-3,3-dimethyloxaziridine 、 N-((1R,2R)-2-aminocyclohexyl)-[1,1':3',1''-terphenyl]-2'-carboxamide 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.5h， 生成 (R)-2-(p-tolyl)propane-1,2-diol
  参考文献：
  名称：

  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes

  摘要：

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.

  DOI：

  10.1021/acs.orglett.5b01193

文献信息

• Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl Peroxide
  作者：Afsaneh Pilevar、Abolfazl Hosseini、Jonathan Becker、Peter R. Schreiner

  DOI：10.1021/acs.joc.9b01748

  日期：2019.10.4

  alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4'-[1,2]dioxolane]-3',5'-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent

  烯烃的顺二羟基化是有机合成中非常有价值的反应。环状酰基过氧化物（CAPs）最近作为有前途的候选物出现，以取代通常用于此目的的有毒金属。在这里，我们证明了结构上苛刻的环状过氧化物螺[双环[2.2.1]庚烷-2,4'-[1,2]二氧戊环] -3'，5'-二酮（P4）可以有效地用于合成烯烃的-二羟基化。与其他CAP和二醇与烯丙醇产品相互竞争的CAP相比，试剂P4还显示出对带有β-氢的烯烃进行二羟基化的选择性提高。此外，对映纯P4（标记为P4'）的使用证明了P4'对于烯烃的无金属不对称顺二羟基化反应的潜力。
• [EN] BENZOXAZINES AS MODULATORS OF ION CHANNELS<br/>[FR] BENZOXAZINES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2013067248A1

  公开（公告）日：2013-05-10

  The invention relates to benzoxazines useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及可用作离子通道抑制剂的苯并噁嗪。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• HETEROCYCLIC CHROMENE-SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS
  申请人：Hadida-Ruah Sara Sabina

  公开号：US20110306607A1

  公开（公告）日：2011-12-15

  The invention relates to heterocyclic chromene-spirocyclic piperidine amides useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及杂环色烯-螺环哌啶酰胺类化合物，其可用作离子通道抑制剂。本发明还提供了包含本发明化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种疾病的方法。
• Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels
  申请人：HADIDA-RUAH Sara Sabina

  公开号：US20140171427A1

  公开（公告）日：2014-06-19

  The invention relates to heterocyclic chromene-spirocyclic piperidine amides useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及杂环色烯-螺环哌啶酰胺，其可用作离子通道抑制剂。本发明还提供了包含该发明化合物的药学上可接受的组合物以及使用该组合物治疗各种疾病的方法。
• BENZOXAZINES AS MODULATORS OF ION CHANNELS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20140309220A1

  公开（公告）日：2014-10-16

  The invention relates to benzoxazines useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及苯并噁唑，其可用作离子通道的抑制剂。本发明还提供了包含本发明化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种疾病的方法。