rel-(2S,3S,4R)-4,5-dimethyl-2-phenyl-1,3-dioxolane | 6666-31-5

• 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: rel-(2S,3S,4R)-4,5-dimethyl-2-phenyl-1,3-dioxolane
• 英文别名: (2S,4R,5S)-4,5-dimethyl-2-phenyl-1,3-dioxolane；4,5-dimethyl-2-phenyl-1,3-dioxolane
• CAS: 6666-31-5
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KELZBYQXUNVXEU-DOFRTFSJSA-N

物化性质

• 沸点：
  251.8±25.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  rel-(2S,3S,4R)-4,5-dimethyl-2-phenyl-1,3-dioxolane 、 氯仿 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 20.0h， 以94%的产率得到2r-Dichlormethyl-4t,5t-dimethyl-2t-phenyl-1,3-dioxolan
  参考文献：
  名称：

  Steinbeck, Karl; Klein, Joachim, Journal of Chemical Research, Miniprint, 1980, # 3, p. 1150 - 1162

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 2,3-丁二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 rel-(2S,3S,4R)-4,5-dimethyl-2-phenyl-1,3-dioxolane 、 rel-(2R,3S,4R)-4,5-dimethyl-2-phenyl-1,3-dioxolane
  参考文献：
  名称：

  缩醛和缩酮的还原裂解与9-硼双环[3.3.1]壬烷†

  摘要：

  苯甲醛缩醛和苯乙酮缩酮与空气稳定的结晶9-borabicyclo [3.3.1]壬烷二聚体的还原裂解分别提供了二醇和1,2-氧-转位的β-苯乙醇的单苄基醚衍生物。通过简单的方法有效地回收硼部分，该方法涉及方便的空气稳定试剂和硼副产物。该方法对于1，3-二醇是特别选择性的，仅给出更多取代的单苄基醚衍生物。用苯乙酮缩酮既发生还原又消除，使9-BBN-H氢硼化所得的苯乙烯，从而干净地生产1,2-氧转位的β-苯乙醇。该新方法的潜在应用已通过迷幻剂，甲斯卡林和止痛药布非那克的合成得到了说明。

  DOI：

  10.1021/op0601262

文献信息

• Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid diols
  作者：Hai-Shan Dang、Brian P. Roberts、Derek A. Tocher

  DOI：10.1039/b309060b

  日期：——

  rearrangement of benzylidene acetals derived from 1,2-diols. Redox rearrangement of the benzylidene acetal from carane-3,4-diol, obtained by cis-dihydroxylation of 3-carene, does not involve intermediate cyclopropylcarbinyl radicals and leads to benzoate ester in which the bicyclic carane skeleton is retained. The inefficient redox rearrangement of the relatively rigid benzylidene acetal from exo,exo-norbornane-2

  从合成和机械的角度研究了衍生自萜烯的1,2-和1,3-二醇的环状亚苄基缩醛的硫醇催化的自由基链氧化还原重排。氧化还原重排在约200℃下进行。70摄氏度（使用Bu（t）ON = NOBu（t）作为引发剂）或达到 在三异丙基甲硅烷硫醇或巯基乙酸甲酯的存在下，在130摄氏度下（使用Bu（t）OOBu（t）作为引发剂）；硅烷硫醇通常更有效。该一般反应提供了单脱氧二醇的苯甲酸酯，除非中间的碳中心自由基的重排在最终被硫醇捕获以得到产物之前发生，在这种情况下，得到结构上重排的酯。对于通过2-烯基的顺式-二羟基化制备的1,2-二醇的亚苄基缩醛，涉及α-pine烯或β-pine烯，中间的环丙基羰基或环丁基羰基，这些基团的开环最终导致不饱和单环苯甲酸酯。在衍生自1,2-二醇的亚苄基缩醛的氧化还原重排过程中，中间β-苯甲酰氧基烷基自由基中的苯甲酸酯基团的1,2-迁移有时还会与硫醇捕获竞争。通过3-烯基的顺式-二
• Mechanism of Chiral Lewis Acid Mediated Enantiotopic Group-Selective Ring Cleavage of Cyclic Acetals Derived from <i>m</i><i>eso</i>-1,2-Diols
  作者：Toshiro Harada、Tomohito Nakamura、Motoharu Kinugasa、Akira Oku

  DOI：10.1021/jo991071n

  日期：1999.10.1

  Diastereoselectivity and enantioselectivity of chiral oxazaborolidine-mediated ring-cleavage reactions of meso-2,4,5-trisubstituted 1,3-dioxolane acetals with a trimethylsilyl ketene acetal were investigated in detail and discussed in terms of a mechanism involving a contact ion pair as a product-forming intermediate. Both diastereomeric 2-phenyl derivatives syn- and anti-11a gave the same ring-cleavage product 13a. However, the reaction of 2-phenylethynyl derivatives syn- and anti-11b proceeded almost stereospecifically, giving rise to 13b and 14b, respectively. In all of the reactions, isomerization of diastereomeric acetals was not observed. On the basis of these results, it was deduced that the dissociation of a: Lewis acid-acetal complex is the rate-determining step, and the resulting ion pair intermediate undergoes either isomerization to a diastereomeric acetal or attack by a nucleophile depending on the structure of the acetal. The possible enantioselection at the product-forming step was ruled out. It was proposed that the observed enantioselectivity is determined by enantiodifferentiating coordination of the acetal oxygen atom by the chiral Lewis acid.
• Desymmetrization of <i>meso</i>-1,2-Diols via Chiral Lewis Acid-Mediated Ring-Cleavage of 1,3-Dioxolane Derivatives
  作者：Motoharu Kinugasa、Toshiro Harada、Akira Oku

  DOI：10.1021/ja9702881

  日期：1997.9.1
• ANTI-MICROBIAL AGENTS AND USES THEREOF
  申请人：Cornell Research Foundation, Inc.

  公开号：US20140024611A1

  公开（公告）日：2014-01-23

  Many pathogens, including Mycobacterium tuberculosis and Yersinia pestis , rely on an iron acquisition system based on siderophores, secreted iron-chelating compounds with extremely high Fe(III) affinity. The compounds of the invention are inhibitors of domain salicylation enzymes, which catalyze the salicylation of an aroyl carrier protein (ArCP) domain to form a salicyl-ArCP domain thioester intermediate via a two-step reaction. The compounds include the intermediate mimic 5′-O—[N-(salicyl)sulfamoyl]-adenosine (salicyl-AMS) and analogs thereof. These compounds are inhibitors of the salicylate activity of MbtA, YbtE, PchD, and other domain salicylation enzymes involved in the biosynthesis of siderophores. Therefore, these compounds may be used in the treatment of infection caused by microorganisms which rely on siderphore-based iron acquisition systems. Pharmaceutical composition and methods of using these compounds to treat or prevent infection are also provided as well as methods of preparing the inventive compounds.
• US8946188B2
  申请人：——

  公开号：US8946188B2

  公开（公告）日：2015-02-03