N-allyl-N-(1-benzyloxymethyl-3-hydroxypent-4-enyl)-4-methylbenzenesulfonamide | 927808-00-2

• 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: N-allyl-N-(1-benzyloxymethyl-3-hydroxypent-4-enyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(2S,4S)-4-hydroxy-1-phenylmethoxyhex-5-en-2-yl]-4-methyl-N-prop-2-enylbenzenesulfonamide
• CAS: 927808-00-2
• 化学式: C₂₃H₂₉NO₄S
• 分子量: 415.554
• InChiKey: ZCFOJMXSLMUSRB-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(1-benzyloxymethyl-3-hydroxypent-4-enyl)-4-methylbenzenesulfonamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到2-benzyloxymethyl-1-(4-methylphenylsulfonyl)-2,3,4,7-tetrahydro-1H-azepin-4-ol
  参考文献：
  名称：

  Synthesis of DMJ analogs with seven- and eight-membered iminocyclitols

  摘要：

  A straightforward synthesis of new hydroxy azepane and azocane with an additional hydroxymethyl side arm (1-deoxymannojirimycin, DMJ analogs) has been achieved from trans-(2S,4R)-4-hydroxyproline via Grignard addition, ring-closing metathesis, and stereoselective osmylation as the key steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.002
• 作为产物：
  描述：

  (2S)-N-allyl-N-[1-benzyloxymethyl-3-(t-butyldimethylsilanyloxy)propyl]-4-methylbenzenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 N-allyl-N-(1-benzyloxymethyl-3-hydroxypent-4-enyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis of DMJ analogs with seven- and eight-membered iminocyclitols

  摘要：

  A straightforward synthesis of new hydroxy azepane and azocane with an additional hydroxymethyl side arm (1-deoxymannojirimycin, DMJ analogs) has been achieved from trans-(2S,4R)-4-hydroxyproline via Grignard addition, ring-closing metathesis, and stereoselective osmylation as the key steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.002

文献信息

• Synthesis of DMJ analogs with seven- and eight-membered iminocyclitols
  作者：Meng-Yang Chang、Yung-Hua Kung、Chih-Chong Ma、Shui-Tein Chen

  DOI：10.1016/j.tet.2006.12.002

  日期：2007.2

  A straightforward synthesis of new hydroxy azepane and azocane with an additional hydroxymethyl side arm (1-deoxymannojirimycin, DMJ analogs) has been achieved from trans-(2S,4R)-4-hydroxyproline via Grignard addition, ring-closing metathesis, and stereoselective osmylation as the key steps. (c) 2006 Elsevier Ltd. All rights reserved.