(2S,3R)-2-(dibenzylamino)-1-phenylundec-4-yn-3-ol | 209341-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-(dibenzylamino)-1-phenylundec-4-yn-3-ol
• CAS: 209341-09-3
• 化学式: C₃₁H₃₇NO
• 分子量: 439.641
• InChiKey: KIPHNTZYTWIVJZ-IOWSJCHKSA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(dibenzylamino)-1-phenylundec-4-yn-3-ol 在 甲醇 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 臭氧 、 乙酰氯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.33h， 生成 (S)-(+)-2-联苄基氨基-3-苯基-1-丙醇
  参考文献：
  名称：

  (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: a new strategy for the asymmetric synthesis of 2-substituted alcohols

  摘要：

  The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the (S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen-or carbon-based 2-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00120-7
• 作为产物：
  描述：

  (S)-(+)-2-联苄基氨基-3-苯基-1-丙醇 在 正丁基锂 、 sulfur(IV) oxide * pyridine 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 3.17h， 生成 (2S,3R)-2-(dibenzylamino)-1-phenylundec-4-yn-3-ol
  参考文献：
  名称：

  (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: a new strategy for the asymmetric synthesis of 2-substituted alcohols

  摘要：

  The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the (S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen-or carbon-based 2-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00120-7

文献信息

• (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: a new strategy for the asymmetric synthesis of 2-substituted alcohols
  作者：Jonathan Clayden、Catherine McCarthy、John G Cumming

  DOI：10.1016/s0957-4166(98)00120-7

  日期：1998.4

  The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the (S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen-or carbon-based 2-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.