(1R,5R,6R)-6-(2,2-dimethylpropanamido)-spiro[4.4]-nonan-1-ol | 575342-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5R,6R)-6-(2,2-dimethylpropanamido)-spiro[4.4]-nonan-1-ol
• 英文别名: N-[(4R,5R,9R)-4-hydroxyspiro[4.4]nonan-9-yl]-2,2-dimethylpropanamide
• CAS: 575342-96-0
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: SNQYOUPXNUBYAF-JTNHKYCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5R,6R)-6-(2,2-dimethylpropanamido)-spiro[4.4]-nonan-1-ol 在 三氯化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] (1R)-4-methylcyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

  摘要：

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00051-x
• 作为产物：
  描述：

  1-(4-羟基丁基)环戊醇 在 吡啶 、 sodium hypochlorite 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 草酸 、 sodium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (1R,5R,6R)-6-(2,2-dimethylpropanamido)-spiro[4.4]-nonan-1-ol
  参考文献：
  名称：

  Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

  摘要：

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00051-x

文献信息

• Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary
  作者：Jeff R. Henderson、Masood Parvez、Brian A. Keay

  DOI：10.1021/ol702280q

  日期：2007.12.1

  A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels-Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels-Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.
• Diastereoselective Diels−Alder Reactions with an Allenyl-Containing Spiro-Amido Chiral Auxiliary
  作者：Jeff R. Henderson、Julian P. Chesterman、Masood Parvez、Brian A. Keay

  DOI：10.1021/jo902556b

  日期：2010.2.5

  A novel allenyl-containing 1,3-spiro-amido alcohol auxiliary has been prepared and used in a variety of diastereo-selective Diels-Alder reactions providing exclusively endo adducts with diastereomeric ratios ranging from 2:1 to > 99:1.