(+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol | 1209-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol
• 英文别名: 2,2-dimethyl-5-phenylpentane-1,3-diol；2,2-Dimethyl-5-phenyl-pentan-1,3-diol；2,2-Dimethyl-5-phenyl-1,3-pentanediol
• CAS: 1209-06-9
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: UQYVIPDHWFDNMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol 在 sodium hypochlorite 、 1,5-dimethyl-9-azanoradamantane N-oxyl 、 四丁基溴化铵 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.07h， 以93%的产率得到(+/-)-3-Hydroxy-2,2-dimethyl-5-phenylvaleraldehyde
  参考文献：
  名称：

  用于醇类选择性氧化的金刚烷金刚烷型硝基氧自由基催化剂的开发

  摘要：

  1,5-二甲基-9- azanoradamantane的发展Ñ -1-氧基（DMN-AZADO; 1,5- d我中号乙基Ñ或-AZADO，2），作为伯醇的存在下选择性氧化的有效的催化剂描述了仲醇的混合物。金刚烷金刚烷核的紧密而刚性的结构赋予了DMN-AZADO强大的催化能力（2）。DMN-AZADO（2）将各种受阻伯醇（例如新戊基伯醇）有效地氧化为相应的醛，而仲醇则保持完整。DMN-AZADO（2）对于在仲醇存在下从伯醇到相应的羧酸的一锅法氧化以及从二醇的氧化内酯化反应也具有很高的催化效率。

  DOI：

  10.1021/jo502426p
• 作为产物：
  描述：

  methyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以73%的产率得到(+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol
  参考文献：
  名称：

  Hydroxyl-Directed Intermolecular Ketone-Olefin Couplings Promoted by SmI2

  摘要：

  SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone - olefin coupling reactions of alpha-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5 H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of beta-hydroxy aldehyde 21 and erythro-beta-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereo-selectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm-III cation, attached to the ketyl radical, with the hydroxyl group.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3252::aid-chem3252>3.0.co;2-d

文献信息

• Germanium(II)-Mediated Reductive Cross-Aldol Reaction of Bromoaldehydes with Aldehydes: NMR Studies and ab Initio Calculations
  作者：Shin-ya Tanaka、Nobuo Tagashira、Kouji Chiba、Makoto Yasuda、Akio Baba

  DOI：10.1021/jo800904u

  日期：2008.8.1

  A highly practical reductive cross-aldol reaction of α-bromoaldehydes with various aldehydes has been developed using Ge(II)Cl2 to produce aldehyde germanium(IV) aldolates, which were directly transformed to various multifunctionalized compounds. A remarkable change in stereoselectivity depended on the α-bromoaldehydes employed; secondary α-bromoaldehydes gave syn selectivities, while tertiary α-bromoaldehydes

  已经开发了使用Ge（II）Cl 2来生产α-溴醛与各种醛的高度实用的还原性醛缩醛反应，可制得醛化锗（IV）醛酸酯，将其直接转化为各种多功能化合物。立体选择性的显着变化取决于所用的α-溴代醛。仲α-溴醛可产生顺式选择性，而叔α-溴醛可完成具有季碳中心的抗选择性羟醛产物的合成。NMR研究和X射线分析强烈表明，α-溴醛2h与GeCl 2反应形成了烯醇锗。-二恶烷。详细的机械研究，包括NMR分析和从头算计算，表明生成稳定的醛缩醛锗，这是由于锗（IV）的路易斯酸度极低所致。
• Lithium Acetate-catalyzed Crossed Aldol Reaction between Aldehydes and Trimethylsilyl Enolates Generated from Other Aldehydes
  作者：Yoshikazu Kawano、Hidehiko Fujisawa、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.614

  日期：2005.4

  Crossed aldol reaction between aromatic aldehydes having an electron-withdrawing group and trimethylsilyl enolates generated from several aldehydes proceeded smoothly in dry or water-containing DMF...

  具有吸电子基团的芳香醛与由几种醛生成的三甲基甲硅烷基烯醇化物之间的交叉羟醛反应在干燥或含水的DMF中顺利进行...
• 9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound
  申请人：TOHOKU UNIVERSITY

  公开号：US09114390B2

  公开（公告）日：2015-08-25

  An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

  一种有机催化剂，用于在具有多个醇的多元醇基质中选择性氧化初级醇，在环境友好条件下进行。有机氧化催化剂具有氧原子与氮原子结合在氮杂诺伦烷骨架的位置1和5上至少一个烷基团。氧化催化剂在初级醇的选择性氧化反应中比现有氧化催化剂TEMPO具有更高的活性，并且比AZADO和1-Me-AZADO具有更好的选择性。这种DMN-AZADO可以应用于对初级醇的选择性氧化反应，有助于缩短制药、制药原料、农药、化妆品、有机材料等高附加值有机化合物的合成过程。
• 9-AZANORADAMANTANE N-OXYL COMPOUND AND METHOD FOR PRODUCING SAME, AND ORGANIC OXIDATION CATALYST AND METHOD FOR OXIDIZING ALCOHOLS USING 9-AZANORADAMANTANE N-OXYL COMPOUND
  申请人：TOHOKU UNIVERSITY

  公开号：US20150031887A1

  公开（公告）日：2015-01-29

  An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

  一种有机催化剂，用于在具有多个醇的多元醇基质中选择性氧化一级醇，以环保条件进行。有机氧化催化剂具有氮杂莫来烷骨架的氧原子与氮原子结合，并且在1和5位置至少有一个烷基基团。在一级醇的选择性氧化反应中，该氧化催化剂比现有的TEMPO具有更高的活性，并且比AZADO和1-Me-AZADO具有更好的选择性。该DMN-AZADO可应用于一级醇的选择性氧化反应，有助于缩短制药、制药原料、农业化学品、化妆品、有机材料等高附加值有机化合物的合成过程。
• US9114390B2
  申请人：——

  公开号：US9114390B2

  公开（公告）日：2015-08-25