3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid | 130822-13-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid
• CAS: 130822-13-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: YDUQGSFTCUKKCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid 在 triphenylmethylium hexachloroantimonate(V) 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 ethyl 4-t-butyldimethylsiloxy-5,5-dimethyl-c-6-phenyethyl-r-2-trichloromethyl-1,3-dioxane-t-4-acetate
  参考文献：
  名称：

  α-取代环醚和syn-1,3-二醇的立体选择性合成

  摘要：

  在催化量的三苯基甲基六氯锑酸盐或五氯化锑、氯三甲基硅烷和碘化锡(II)的催化体系存在下，通过1-(叔丁基二甲基甲硅烷氧基)-1-连续处理，由内酯立体选择性地制备α-取代环醚乙氧基乙烯和甲硅烷基亲核试剂，例如三乙基硅烷、烯丙基三甲基硅烷和三甲基硅烷基氰化物。这些催化剂还促进 γ-、δ-和 e-三甲基甲硅烷氧基羰基化合物与甲硅烷基亲核试剂的反应，从而形成 α-取代的环醚。前一种程序有效地应用于 (-)-顺式玫瑰氧化物和 (cis-6-methyltetrahydro-2-pyranyl) 乙酸（一种麝猫香的成分）的短程合成。此外，syn-1,3-二醇也由内酯类似物立体选择性地制备，

  DOI：

  10.1246/bcsj.63.1898
• 作为产物：
  描述：

  ethyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate 在 甲醇 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以80%的产率得到3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• 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。
• Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes
  作者：Yoshihiro Inamoto、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol3001443

  日期：2012.2.17

  An indium triiodide catalyst promoted the direct transformation from esters to beta-hydroxycarbonyl compounds using hydrosilanes and silyl enolates by a one-stage process. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups: alkenyl, alkynyl, chloro, and hydroxy.
• HOMMA, KOICHI;TAKENOSHITA, HARUHIRO;MUKAIYAMA, TERUAKI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 1898-1915
  作者：HOMMA, KOICHI、TAKENOSHITA, HARUHIRO、MUKAIYAMA, TERUAKI

  DOI：——

  日期：——
• US9114390B2
  申请人：——

  公开号：US9114390B2

  公开（公告）日：2015-08-25