<5S>-3-isopropyl-5-(1-naphthyloxymethyl)-oxazolidin-2-one | 81102-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: <5S>-3-isopropyl-5-(1-naphthyloxymethyl)-oxazolidin-2-one
• 英文别名: (S)-3-isopropyl-5-((naphthalen-4-yloxy)methyl)oxazolidin-2-one；(5S)-5-(naphthalen-1-yloxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 81102-74-1
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: NFYJEFQNQKQGSK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <5S>-3-isopropyl-5-(1-naphthyloxymethyl)-oxazolidin-2-one 生成 盐酸普奈洛尔
  参考文献：
  名称：

  LINDNER, WOLFGANG

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl N-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-N-propan-2-ylcarbamate 在 吡啶 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 <5S>-3-isopropyl-5-(1-naphthyloxymethyl)-oxazolidin-2-one
  参考文献：
  名称：

  Tsuda, Yoshisuke; Yoshimoto, Kimihiro; Nishikawa, Terumi, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 12, p. 3593 - 3600

  摘要：

  DOI：

文献信息

• Method of preparing a heterocyclic intermediate for the production of optically active aryloxysubstituted vicinal aminoalcohols
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0647633A1

  公开（公告）日：1995-04-12

  The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein    X is a carbonyl group, a thiocarbonyl group, a (C₁-C₁₀)(ar)alkylidene group or a dihydrocarbylsilyl group,    R is a straight or branched (C₁-C₁₀)alkyl group, optionally substituted with halogen, hydroxy, (C₁-C₄)alkoxy or protected hydroxy, or a phenyl(C₁-C₃)alkyl or heteroaryl(C₁-C₃)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C₅-C₁₂)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms, and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH₂ as the primary amine, followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.

  本发明涉及一种制备杂环中间体的方法，其通式如下：其中X为羰基，硫代羰基，(C₁-C₁₀)(芳)烷基亚甲基或二氢基碳基硅基，R为直链或支链(C₁-C₁₀)烷基，可选用卤素、羟基、(C₁-C₄)烷氧基或保护羟基进行取代，或苯基(C₁-C₃)烷基或杂环芳基(C₁-C₃)烷基，这些基团可选用1-3个取代基进行取代，所述取代基选自羟基、(C₅-C₁₂)环烷基、氨基、硝基、卤素、氰基、烷氧基、烷基羰氧基、烷基羰基氨基、烷基磺酰胺基、烷基磺酰基、烷基羰基和烷基，其中烷基含有1-5个碳原子，该中间体具有R或S构型，通过将手性氰醇通式的还原-转移-还原序列，使用R-NH₂作为主要胺，然后进行环化反应，最后进行臭氧化-还原序列。
• Method of preparing a heterocyclic intermediate for the production of optically active aryloxy-substituted vicinal aminoalcohols
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0647634A1

  公开（公告）日：1995-04-12

  The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein    X is a carbonyl group, a thiocarbonyl group, a (C₁-C₁₀)(ar)alkylidene group or a dihydrocarbylsilyl group,    R is a straight or branched (C₁-C₁₀)alkyl group, optionally substituted with halogen, hydroxy, (C₁-C₄) alkoxy or protected hydroxy, or a phenyl(C₁-C₃)alkyl or heteroaryl(C₁-C₃)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C₅-C₁₂)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms, and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH₂ as the primary amine, followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.

  本发明涉及一种通式如下的杂环中间体的制备方法 其中 X 是羰基、硫代羰基、(C₁-C₁₀)(ar)亚烷基或二氢羰基硅烷基、 R 是直链或支链(C₁-C₁₀)烷基，可选择被卤素、羟基、(C₁-C₄)烷氧基或受保护羟基取代，或苯基(C₁-C₃)烷基或杂芳基(C₁-C₃)烷基，这些基团可选择被 1-3 个取代基取代、选自由羟基、(C₅-C₁₂)环烷基、氨基、硝基、卤素、氰基、烷氧基、烷基羰氧基、烷基羰基氨基、烷基磺酰基氨基、烷基磺酰基、烷基羰基和烷基组成的组，其中烷基具有 1-5 个碳原子、 将通式如下的具有光学活性的氰醇与具有 R 或 S 构型的中间体反应 以 R - NH₂ 作为伯胺，进行还原-反式-还原反应、 然后进行环化反应，最后进行臭氧分解还原反应。
• Concise Synthesis of Two β-Adrenergic Blocking Agents in High Stereoselectivity Using the Readily Available Chiral Building Block (2<i>S</i>,2′<i>S</i>,2″<i>S</i>)-Tris-(2,3-epoxypropyl)-isocyanurate
  作者：Swapnil P. Sonawane、Gulabrao D. Patil、Mukund K. Gurjar

  DOI：10.1021/op2001518

  日期：2011.11.18

  A concise synthesis of (S)-propranolol and (S)-metoprolol in high stereoselectivity using the readily available chiral building block (2S,2'S,2 '' S)-tris-(2,3-epoxypropyl)-isocyanurate (S-TGT) as the key intermediate is described.
• Kan, Kazunori; Miyama, Akimasa; Hamaguchi, Shigeki, Agricultural and Biological Chemistry, 1985, vol. 49, # 1, p. 207 - 210
  作者：Kan, Kazunori、Miyama, Akimasa、Hamaguchi, Shigeki、Ohashi, Takehisa、Watanabe, Kiyoshi

  DOI：——

  日期：——
• LINDNER, WOLFGANG
  作者：LINDNER, WOLFGANG

  DOI：——

  日期：——