(R)-2-hydroxy-N-methoxy-N-methylpropanamide | 207680-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-hydroxy-N-methoxy-N-methylpropanamide
• 英文别名: (2R)-2-hydroxy-N-methoxy-N-methylpropanamide
• CAS: 207680-77-1
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: KBXKYDCTTSQLNA-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-N-methoxy-N-methylpropanamide 在 三乙烯二胺 、 硝基甲烷 、 potassium carbonate 、 zinc dibromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (2S)-2-[2-bromo-6-[(Z)-heptadec-10-enyl]-3-hydroxyphenoxy]-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  General Synthesis for Chiral 4-Alkyl-4-hydroxycyclohexenones

  摘要：

  Some selective transformations of resorcinol-derived cyclohexadienone are reported. Efforts led to a structure reported to display anticancer properties. On the basis of the results, the structures for natural products reported to contain a 4,6-dihydroxy-4-alkyl-cyclohexenone nucleus are corrected.

  DOI：

  10.1021/ol061000s
• 作为产物：
  描述：

  (R)-乳酸异丁酯 、 二甲羟胺盐酸盐 在 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (R)-2-hydroxy-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  Studies in polypropionate synthesis: High π-face selectivity in syn and anti aldol reactions of chiral boron enolates of lactate-derived ketones

  摘要：

  Use of (c)Hex(2)BCl/Me(2)NEt in the aldol reactions of the alpha'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-99.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.

  DOI：

  10.1016/0040-4039(94)88434-x

文献信息

• Total Synthesis of (+)-Rishirilide B:  Development and Application of General Processes for Enantioselective Oxidative Dearomatization of Resorcinol Derivatives
  作者：Lupe H. Mejorado、Thomas R. R. Pettus

  DOI：10.1021/ja062987w

  日期：2006.12.1

  amide of dimethylhydrazine for opening and cleavage of a [1,4]-dioxan-2-one is also described. This procedure unmasks the hydroxy dione 36 by jettisoning the chiral directing group. Regioselective O-carbamylation of the 1,3-dione 36 enables the transformation of the remaining carbonyl into the alpha-hydroxy carboxylic acid found in 2. The total synthesis of (+)-rishirilide B (2) requires 15 pots from

  描述了 (+)-rishirilide B (2) 的简明合成。这是自然界中发现的 rishirilide B (2) (+)-对映体的首次合成报道。该策略强调了邻醌甲基化物偶联方法与对映选择性间苯二酚脱芳构化方法的有价值的组合，提供了密集功能化的手性结构单元。收敛合成说明了这些方法及其支持化学的一些改进和改进。其中包括 PhI[OTMS]OTf 的原位生成。该氧化剂与苯酚31的组合构成了具有2-烷基取代基的间苯二酚的非对映选择性氧化脱芳构化的第一个实例。此外，还报道了环砜34的制备。作为一种表达易于裂解的 O-苄基残基的新型二甲基化物前体，砜 34 在未来的研究中应该会被证明是有用的。还描述了使用二甲基肼的氨基铝来打开和裂解[1,4]-二恶烷-2-酮的方案。该过程通过抛弃手性导向基团来揭示羟基二酮 36。1,3-二酮 36 的区域选择性 O-氨甲酰化能够将剩余的羰基转化为 2 中的 α-羟基羧酸。
• Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments
  作者：Todd A. Wenderski、Shenlin Huang、Thomas R. R. Pettus

  DOI：10.1021/jo900401k

  日期：2009.6.5

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.
• Polyketide Synthesis Using the Boron-Mediated, anti-Aldol Reactions of Lactate-Derived Ketones: Total Synthesis of (-)-ACRL Toxin IIIB
  作者：Ian Paterson

  DOI：10.1055/s-1998-5929

  日期：1998.3

  The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reagent control operates with chiral aldehydes. These lactate-derived ketones provide a versatile chiral auxiliary for the synthesis of beta-hydroxy carbonyl compounds. Oxidative removal of the auxiliary provides enantiomerically pure aldehydes 5, while reductive deoxygenation gives the corresponding ethyl ketones 6. This practical asymmetric methodology for generating anti-aldols is illustrated by an efficient total synthesis of (-)-ACRL toxin IIIB (7), which proceeds in 15 steps from 2 with 21% overall yield and 88% diastereoselectivity.
• The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form
  作者：Shigekazu Sasaki、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(99)00411-6

  日期：1999.4

  The title acid, a component of microsclerodermins of marine sponge origin having five consecutive stereogenic centers, was efficiently synthesized as its protected form 1 from the alcohol 5 utilizing the stereoselective addition of anisole to the acetylenic triple bond and the anti-aldol reaction as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.
• WO2024097953A1
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  公开号：——

  公开（公告）日：——