N-(3-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}-1,1-bis(hydroxymethyl)propyl)acetamide | 1023648-29-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(3-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}-1,1-bis(hydroxymethyl)propyl)acetamide
• 英文别名: N-[4-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl]acetamide
• CAS: 1023648-29-4
• 化学式: C₂₆H₂₈ClNO₄S
• 分子量: 486.032
• InChiKey: LRDCDUNLDKSTAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}-1,1-bis(hydroxymethyl)propyl)acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到2-氨基-2-[2-[2-氯-4-[[3-(苄氧基)苯基]硫]苯基]乙基]-1,3-丙二醇盐酸盐
  参考文献：
  名称：

  An efficient total synthesis of a sphingosine-1-phosphate receptor agonist KRP-203

  摘要：

  An efficient total synthesis of the S1P(1) agonist, KRP-203, is described. The key step involves the conjugate addition of diethyl acetamidomalonate to a styrene compound to give the core structure of KRP-203. Multigram quantities of the targeted KRP-203, sufficient for several biological studies, were obtained in six steps with an overall yield of 58%. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.086
• 作为产物：
  描述：

  2-acetamido-2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)malonic acid diethyl ester 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到N-(3-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}-1,1-bis(hydroxymethyl)propyl)acetamide
  参考文献：
  名称：

  An efficient total synthesis of a sphingosine-1-phosphate receptor agonist KRP-203

  摘要：

  An efficient total synthesis of the S1P(1) agonist, KRP-203, is described. The key step involves the conjugate addition of diethyl acetamidomalonate to a styrene compound to give the core structure of KRP-203. Multigram quantities of the targeted KRP-203, sufficient for several biological studies, were obtained in six steps with an overall yield of 58%. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.086

文献信息

• An efficient total synthesis of a sphingosine-1-phosphate receptor agonist KRP-203
  作者：Masao Chino、Masatoshi Kiuchi、Kunitomo Adachi

  DOI：10.1016/j.tet.2008.01.086

  日期：2008.4

  An efficient total synthesis of the S1P(1) agonist, KRP-203, is described. The key step involves the conjugate addition of diethyl acetamidomalonate to a styrene compound to give the core structure of KRP-203. Multigram quantities of the targeted KRP-203, sufficient for several biological studies, were obtained in six steps with an overall yield of 58%. (c) 2008 Elsevier Ltd. All rights reserved.