(1R,5R,6R)-6-aminospiro[4.4]nonan-1-ol | 575342-84-6

• 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-aminospiro[4.4]nonan-1-ol
• 英文别名: (4R,5R,9R)-9-aminospiro[4.4]nonan-4-ol
• CAS: 575342-84-6
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: RMPOVHNVHWIJIZ-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 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-aminospiro[4.4]nonan-1-ol 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] prop-2-enoate
  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 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 48.0h， 生成 (1R,5R,6R)-6-aminospiro[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

• Development of P-stereogenic 2-phenyl-1,3,2-oxazaphosphorine ligands and their unexpected sensitivity to oxidation
  作者：Wendy L. Benoit、Masood Parvez、Brian A. Keay

  DOI：10.1016/j.tetasy.2008.12.027

  日期：2009.1

  P-Stereogenic oxazaphosphorine compounds of the form 4 have not previously been reported as asymmetric ligands for metal-catalyzed reactions. In an effort to explore the behavior of such oxazaphosphorine ligands, monomeric oxazaphosphorine borane 9 and dimeric oxazaphosphorine boranes 25 and 26 were synthesized as catalyst precursors. The absolute configuration of the phosphorus center contained in

  先前尚未报道形式4的对-立体异构的氧杂磷膦化合物作为金属催化反应的不对称配体。为了探索此类草根磷化氢配体的行为，单体草根磷化氢硼烷9和二聚草根磷化氢硼烷25和26被合成为催化剂的前体。氧杂氮杂膦中所含的磷中心的绝对构型通过X射线晶体学测定。使用二聚螺旋氧杂氮杂磷配体进行铑催化的2-乙酰氨基丙烯酸甲酯的氢化反应，其ee最高可达15％。草氮磷膦配体对氧化的极端敏感性阻止了对映选择性的进一步优化。
• Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions
  作者：Susan M. Lait、Masood Parvez、Brian A. Keay

  DOI：10.1016/s0957-4166(03)00051-x

  日期：2003.3

  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.