(2R,3R,6E,8S,10S)-1-(4-hydroxyphenyl)-8,10-dimethyl-2-(methylamino)dodec-6-en-3-ol | 1093661-46-1

• 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: (2R,3R,6E,8S,10S)-1-(4-hydroxyphenyl)-8,10-dimethyl-2-(methylamino)dodec-6-en-3-ol
• 英文别名: tyroscherin；4-[(E,2R,3R,8S,10S)-3-hydroxy-8,10-dimethyl-2-(methylamino)dodec-6-enyl]phenol
• CAS: 1093661-46-1
• 化学式: C₂₁H₃₅NO₂
• 分子量: 333.514
• InChiKey: RNCWKUCWPBNWOH-RJCOHJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl (1R,2R,5E,7S,9S)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-7,9-dimethylundec-5-enyl]methylcarbamate 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以100%的产率得到(2R,3R,6E,8S,10S)-1-(4-hydroxyphenyl)-8,10-dimethyl-2-(methylamino)dodec-6-en-3-ol
  参考文献：
  名称：

  Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells

  摘要：

  Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1 -dependent cancer cells, was succeeded by one-pot Julia Coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.003

文献信息

• Synthesis and structure revision of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells
  作者：Ryo Katsuta、Chié Shibata、Ken Ishigami、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tetlet.2008.09.141

  日期：2008.12

  Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1-dependent cancer cells, was succeeded by one-pot Julia coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin was revised to be 2S,3R,8R,10R by syntheses of stereoisomers.

  一锅Julia偶联成功合成了拟议的酪氨酸蛋白结构，酪氨酸蛋白蛋白是IGF-1依赖性癌细胞的生长抑制剂。但是，合成化合物的光谱数据与天然酪氨酸的光谱数据不同。通过合成立体异构体，酪氨酸的立体化学被修改为2 S，3 R，8 R，10 R。
• Total Synthesis and Biological Evaluation of Tyroscherin
  作者：Hyun Seop Tae、John Hines、Ashley R. Schneekloth、Craig M. Crews

  DOI：10.1021/ol101801u

  日期：2010.10.1

  The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.
• Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells
  作者：Ken Ishigami、Ryo Katsuta、Chié Shibata、Yoichi Hayakawa、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tet.2009.03.003

  日期：2009.5

  Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1 -dependent cancer cells, was succeeded by one-pot Julia Coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.