(2R,3S)-2-amino-11-methyldodecan-3-ol | 1196960-20-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3S)-2-amino-11-methyldodecan-3-ol
• CAS: 1196960-20-9
• 化学式: C₁₃H₂₉NO
• 分子量: 215.379
• InChiKey: HZFYLRXGLUPZTG-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• 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

• 作为产物：
  描述：

  (2R,3S)-2-(dibenzylamino)-11-methyldodecan-3-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以86%的产率得到(2R,3S)-2-amino-11-methyldodecan-3-ol
  参考文献：
  名称：

  Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

  摘要：

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.010

文献信息

• Clavaminols G–N, six new marine sphingoids from the Mediterranean ascidian Clavelina phlegraea
  作者：Anna Aiello、Ernesto Fattorusso、Antonella Giordano、Marialuisa Menna、Carmen Navarrete、Eduardo Muñoz

  DOI：10.1016/j.tet.2009.03.056

  日期：2009.5

  An exhaustive examination of the chemical constituents of the Mediterranean ascidian Clavelina phlegraea led to the isolation of clavaminols G-N (1-6), a new series of amino alcohols, which expand the family of modified marine sphingoids. Structures of the novel compounds 1-6 have been elucidated by spectroscopic analysis and chemical derivatization: bioactivities of compounds 1-6 have also been investigated and comparison of their pharmacological properties with those of previously isolated clavaminols A-F allowed us to perform an assessment of simple structure-activity relationships. (C) 2009 Elsevier Ltd. All rights reserved.
• Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols
  作者：Bi-Shuang Chen、Long-He Yang、Jian-Liang Ye、Tao Huang、Yuan-Ping Ruan、Jin Fu、Pei-Qiang Huang

  DOI：10.1016/j.ejmech.2011.09.010

  日期：2011.11

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.