(4R,5R)-4-(1''-pyrrolidino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone | 117553-99-8

• 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: (4R,5R)-4-(1''-pyrrolidino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone
• 英文别名: (4R,5R)-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-4-pyrrolidin-1-yloxolan-2-one
• CAS: 117553-99-8
• 化学式: C₁₈H₃₁NO₃
• 分子量: 309.449
• InChiKey: UBAJUOWEMXATCC-ORDFZIBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-(1''-pyrrolidino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(R)-2-pyrrolidino-1,4-butanediol
  参考文献：
  名称：

  Asymmetric synthesis of 2-amino-1,4-diols

  摘要：

  DOI：

  10.1016/s0040-4039(00)80283-x
• 作为产物：
  描述：

  1-allyl-pyrrolidine 、 (5R)-(L-menthyloxy)-2(5H)-furanone 在 4,4'-二甲氧基二苯甲酮 作用下， 以53%的产率得到(4R,5R)-4-(1''-pyrrolidino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone
  参考文献：
  名称：

  Diastereoselective Tandem Addition−Cyclization Reactions of Unsaturated Tertiary Amines Initiated by Photochemical Electron Transfer (PET)

  摘要：

  Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of or-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is greater than or equal to 90%. The alpha -aminoalkyl radicals were produced from tertiary amines by photachemical-induced electron transfer. When N,N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of 1 during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tettahydroquinolines 21a-i, 22a-f, and 26g-i were doubled.

  DOI：

  10.1021/jo001166l

文献信息

• Asymmetric 1, 4-additions to 5-alkoxy-2 (5H)-furanonesenantioselective synthesis and absolute configuration determination of β-amino-δ-butyrolactones and amino diols
  作者：B. de Lange、F. van Bolhuis、Ben L. Feringa

  DOI：10.1016/s0040-4020(01)89149-3

  日期：1989.1

  es via asymmetric conjugate addition of various amines to 5-menthyloxy-2(5H)-furanone is described. This route provides access to new multifunctionalhomochiral building blocks. The absolute configuration of the β-amino-δ-butyrolactones is established by X-ray analysis and 1H NMR correlation. Theconjugate addition of amines to 2[5H]-furanone, 5-alkyl-2[5H]-furanones and 5-alkoxy-2[5H]-furanones was

  描述了通过将各种胺不对称共轭加成到5-薄荷基氧基-2（5H）-呋喃酮中来合成对映体纯的β-氨基-δ-丁内酯。这条路线提供了通往新的多功能同构构件的途径。通过X射线分析和1 H NMR相关性确定了β-氨基-δ-丁内酯的绝对构型。研究了将胺共轭添加到2 [5H]-呋喃酮，5-烷基-2 [5H]-呋喃酮和5-烷氧基-2 [5H]-呋喃酮中，并观察到由于2 [5H]-呋喃酮具有增强的反应性，这是由于γ-烷氧基效应。不对称胺加成的合成效用以有效途径说明了各种光学纯的2-氨基-1，4-丁二醇的合成。
• Highly Efficient and Stereoselective Radical Addition of Tertiary Amines to Electron-Deficient Alkenes − Application to the Enantioselective Synthesis of Necine Bases
  作者：Samuel Bertrand、Norbert Hoffmann、Jean-Pierre Pete

  DOI：10.1002/1099-0690(200006)2000:12<2227::aid-ejoc2227>3.3.co;2-#

  日期：2000.6
• FERINGA, BEN L.;DE, LANGE B., TETRAHEDRON LETT., 29,(1988) N 11, 1303-1306
  作者：FERINGA, BEN L.、DE, LANGE B.

  DOI：——

  日期：——