(1S,2R,4R)-2-hydroxy-7,7-dimethyl-N,N-diethylbicyclo[2.2.1]heptane-1-carboxamide | 1193320-09-0

• 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,2R,4R)-2-hydroxy-7,7-dimethyl-N,N-diethylbicyclo[2.2.1]heptane-1-carboxamide
• 英文别名: (1S,2R,4R)-N,N-diethyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxamide
• CAS: 1193320-09-0
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: WPUNSUZYCVLLSP-GYSYKLTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-2-hydroxy-7,7-dimethyl-N,N-diethylbicyclo[2.2.1]heptane-1-carboxamide 在 叔丁醇 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  手性醇取代的乙烯基氨基甲酸酯的抗Aldol反应与（-）-内酯B的合成

  摘要：

  本文描述了一种方便有效的合成手性醇取代的乙烯基氨基甲酸酯的方法，其中通过单晶X射线分析确定了具有E构型的双键。另外，我们研究了这些手性乙烯基类氨基甲酸酯阴离子的抗醛醇缩合反应。使用（1 S，2 R，4 R）-1-（羟基二苯甲基）-7,7-二甲基双环[2,2,1]-庚-2-醇作为手性助剂，可提供最佳对映选择性，并且所得的乙烯基类氨基甲酸酯内酯可用于合成（-）-内酯B。讨论了主要对映异构体生成的合理机理。

  DOI：

  10.1016/j.tet.2010.12.009
• 作为产物：
  描述：

  (1S,4R)-N,N-diethyl-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (1S,2R,4R)-2-hydroxy-7,7-dimethyl-N,N-diethylbicyclo[2.2.1]heptane-1-carboxamide
  参考文献：
  名称：

  Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation

  摘要：

  This paper describes a method for the intramolecular anodic oxidation of omega-hydroxyl amides. Products were obtained in acceptable yields from different starting materials using various applied currents, charge, and reactant concentrations. Compounds 1a and 1d afforded a single diastereomer in 67% yield when the applied current and reactant concentration were 100 mA and 0.04 M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.017

文献信息

• anti-Selective aldol reactions of chiral alcohol substituted γ-benzyloxyl vinylogous urethanes and the synthesis of 3-benzyloxyl-4-hydroxylalkan-2-ones
  作者：Yu-Jang Li、Chuan-Chung Chung、Pin-Zu Chen

  DOI：10.1016/j.tetasy.2017.10.003

  日期：2017.11

  The anti-selective aldol reaction of chiral alcohol-substituted gamma-benzyloxy vinylogous urethanes is described. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2,1]-heptan-2-ol as a chiral auxiliary in the aldol reaction of a vinylogous urethane enolate was found to provide anti-products in good yields with moderate to excellent enantioselectivities. The major anti-vinylogous urethane lactones were transformed into 3-benzyloxyl-4-hydroxylalkan-2-ones in good yields. (C) 2017 Elsevier Ltd. All rights reserved.
• Asymmetric [2,3]-Wittig rearrangement of the dienolates of chiral secondary alcohol-substituted β-pyrrolidinyl-γ-allyloxyl-α,β-unsaturated esters: total synthesis of (+)-eldanolide
  作者：Yu-Jang Li、Guo-Ming Ho、Pin-Zu Chen

  DOI：10.1016/j.tetasy.2009.07.028

  日期：2009.8

  The asymmetric [2,3]-Wittig rearrangement of the dienolates of various chiral beta-pyrrolidinyl-gamma-allyloxyl-alpha,beta-unsaturated esters was investigated using different chiral secondary alcohol Substitutions. When (1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2,2,1]heptane-1-carboxylic acid diisopropylamide was used as chiral auxiliary, it provided the best enantioselectivity in the rearrangement. When various gamma-allyloxy substitutions underwent temperature and additive studies, 1,1-dimethylpropenoxy substitution was found to give the best enantioselectivity. The methodology was applied to the total synthesis of eldanolide. (C) 2009 Elsevier Ltd. All rights reserved.