(1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide | 256393-10-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide
• 英文别名: (1R,2S,5'S)-N,N-diisopropyl-[2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide；N,N-di(propan-2-yl)-1-[(1'S,2S,4S,4'R)-4,7',7'-trimethyl-5-oxospiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]-1'-yl]methanesulfonamide
• CAS: 256393-10-9
• 化学式: C₁₉H₃₃NO₅S
• 分子量: 387.541
• InChiKey: GQARGMOMMUGTRV-QXGSTGNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 30.5h， 生成 (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide
  参考文献：
  名称：

  摘要：

  DOI：

  10.5555/ol0069507
• 作为产物：
  描述：

  (1S)-N,N-diisopropyl (2,2-dimethoxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide 、 乳酸 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 以77%的产率得到(1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide
  参考文献：
  名称：

  Enantioselective Synthesis of α-Hydroxy Acids Employing (1S)-(+)-N,N-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary

  摘要：

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.

  DOI：

  10.1021/ol9910666

文献信息

• Asymmetric Synthesis of (-)-Pterosin N from a Chiral 1,3-Dioxolanone
  作者：Hsiu-Han Wu、Shao-Chien Hsu、Feng-Lin Hsu、Biing-Jiun Uang

  DOI：10.1002/ejoc.201402234

  日期：2014.7

  asymmetric total synthesis of (–)-pterosin N from the N,N-diisopropyl-10-camphorsulfonamide-derived chiral 1,3-dioxolanone 11 has been accomplished in 9 steps with 8 % overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3-dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene-ynone by Stille coupling, and an intramolecular Diels–Alder

  从 N,N-二异丙基-10-樟脑磺酰胺衍生的手性 1,3-二氧戊环酮 11 第一次不对称全合成 (-)-pterosin N 已分 9 个步骤完成，总产率为 8%。该合成的关键步骤是 1,3-二氧戊环酮 11 的高度立体选择性炔丙基化以构建手性叔醇部分，通过 Stille 偶联构建二烯-炔酮，以及分子内 Diels-Alder 反应，然后进行芳构化以完成合成.
• Process for preparing optically active &agr;-hydroxy acids and derivatives thereof
  申请人：Chan Hardy W.

  公开号：US06639095B1

  公开（公告）日：2003-10-28

  The present invention provides a process for preparing optically active &agr;-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1 and R2 are the same or different and are each independently H or C1-6 alkyl; R5 is H, C1-16 alkyl, or unsubstituted or substituted phenyl; and R6 is C1-8 alkyl, C2-7 alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.

  本发明提供了一种制备光学活性α-羟基酸及其衍生物的方法，通过将具有化学式（IV）的烷基化1,3-二氧杂环酮暴露于醇解或水解条件下，其中R1和R2相同或不同，分别独立地为H或C1-6烷基；R5为H、C1-16烷基，或未取代或取代的苯基；R6为C1-8烷基、C2-7烯基或未取代或取代的苄基，所述烷基化1,3-二氧杂环酮是通过使用10-樟脑磺酰胺作为手性辅助剂获得的。
• Stereoselective Michael-alkylation and Michael-oxidation reactions of chiral 1,3-dioxolanones
  作者：Hao-Chun Liao、Kuan-Jen Yao、Yi-Chou Tsai、Biing-Jiun Uang

  DOI：10.1016/j.tetasy.2017.05.002

  日期：2017.6

  A highly diastereoselective Michael-alkylation/oxidation methodology has been developed for the synthesis of optically active alpha-hydroxy-1,5-diester subunits. Inverse stereochemistry at the C-2' position could be achieved by using a Michael acceptor equipped with a suitable group followed by a highly stereoselective protonation. This methodology has been applied to the enantioselective synthesis of the upper fragment of (+)-retusine. (C) 2017 Elsevier Ltd. All rights reserved.
• ——
  作者：D.-P. Jang、J.-W. Chang、B.-J. Uang

  DOI：10.5555/ol0069507

  日期：2001.4.5
• Enantioselective Synthesis of <i>α</i>-Hydroxy Acids Employing (1<i>S</i>)-(+)-<i>N</i>,<i>N</i>-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary
  作者：Jia-Wen Chang、Der-Pin Jang、Biing-Jiun Uang、Fen-Ling Liao、Sue-Lein Wang

  DOI：10.1021/ol9910666

  日期：1999.12.1

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.