12-aminodehydroabietic acid, methyl ester | 30885-12-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 12-aminodehydroabietic acid, methyl ester
• 英文别名: methyl 12-aminodehydroabietate；12-aminodehydroabietate；12-amino-abieta-8,11,13-trien-18-oic acid methyl ester；12-Amino-abieta-8,11,13-trien-18-saeure-methylester；12-Amino-13-isopropyl-podocarpatrien-(C)-saeure-(15)-methylester；12-Amino-13-isopropyl-podocarpatrien-(8.11.13)-saeure-(15)-methylester；methyl (1R,4aS,10aR)-6-amino-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 30885-12-2；35940-42-2
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: AUHIYXMJLOPKFL-HMXCVIKNSA-N

物化性质

• 沸点：
  437.5±45.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-aminodehydroabietic acid, methyl ester 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以68%的产率得到12-aminodehydroabietic acid
  参考文献：
  名称：

  含有脱氢松香酸骨架的新型BK通道开放剂：环C上外围取代基的结构活性关系。

  摘要：

  合成了一系列脱氢松香酸（DHAA，2）衍生物，并在表达hBKalpha通道的CHO-K1细胞分析系统中将其作为BK通道开放剂进行评估。DHAA的C环外围功能的系统修饰表明，在C环中引入硝基或（硫）脲基可大大增强BK通道的开放活性。

  DOI：

  10.1016/j.bmcl.2008.08.078
• 作为产物：
  描述：

  13-isopropyl-12-acetohydroximoyl-podocarpatrien-(C)-oic acid-(15)-methyl ester 在 盐酸 、 乙酸酐 、 溶剂黄146 作用下， 生成 12-aminodehydroabietic acid, methyl ester
  参考文献：
  名称：

  Hydroxyl and Amino Derivatives of Dehydroabietic Acid and Dehydroabietinol

  摘要：

  DOI：

  10.1021/ja01878a080

文献信息

• N-heterocyclic carbenes. IV.1synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety
  作者：V. A. Glushkov、K. A. Arapov、M. S. Kotelev、K. S. Rudowsky、K. Yu. Suponitsky、A. A. Gorbunov、O. A. Maiorova、P. A. Slepukhin

  DOI：10.1002/hc.20745

  日期：——

  12-chloromethyl-dehydroabie-tate reacts with 1-benzyl- and 1-arylimidazoles to give unsymmetrically substituted imidazolium chlorides (1a–i), with abietane moiety. Starting from methyl 12-aminodehydroabietate, symmetrically substituted diterpene-based salts of imidazolinium (4) and imidazolium (5) were synthesized. Anion exchange afforded corresponding (1e·BF4) and (1e·PF6). The new compounds were tested

  12-氯甲基-脱氢松香酸甲酯与 1-苄基-和 1-芳基咪唑反应生成不对称取代的咪唑氯化物 (1a-i)，带有松香烷部分。从 12-氨基脱氢松香酸甲酯开始，合成了对称取代的基于二萜的咪唑啉 (4) 和咪唑 (5) 盐。阴离子交换得到相应的(1e·BF4)和(1e·PF6)。新化合物作为 Pd 催化的 Suzuki-Miyaura 反应的配体进行了测试。报道了(1e)的分子结构。© 2011 Wiley Periodicals, Inc. 杂原子化学 23:5–15, 2012; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20745
• Synthesis of heterocyclic derivatives of abietane
  作者：V. A. Glushkov、A. V. Tarantin、V. I. Karmanov、A. G. Tolstikov

  DOI：10.1134/s1070427210080331

  日期：2010.8

  The methods of synthesis of some new derivatives of abietane including pyridines and indoles fused with diterpene skeleton were described.

  描述了一些合成的枞豆新衍生物的方法，包括吡啶和吲哚与二萜骨架融合的吲哚。
• The povarov reaction of cyclopentadiene with imines from methyl 12-amino-dehydroabietate
  作者：A. G. Tolstikov、V. A. Glushkov、A. V. Tarantin、G. F. Kazanbaeva、A. S. Shashkov、K. Yu. Suponitsky、V. M. Dembitsky

  DOI：10.1002/hc.20159

  日期：——

  The aza-Diels-Alder cycloaddition reaction of cyclopentadiene with benzylideneanilines from methyl 12-amino-dehydroabietate is described via the Povarov reaction. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:605–612, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20159

  环戊二烯与来自 12-氨基-脱氢松香酸甲酯的亚苄基苯胺的 aza-Diels-Alder 环加成反应通过 Povarov 反应进行了描述。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:605–612, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20159
• Ochiai; Ohta, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 203
  作者：Ochiai、Ohta

  DOI：——

  日期：——
• Synthetic Derivatives of Abietic Acid with Radical Scavenging Activity
  作者：M. Alexandra Esteves、Nama Narender、Maria J. Marcelo-Curto、Bárbara Gigante

  DOI：10.1021/np000501y

  日期：2001.6.1

  In this work, studies on the arylation of anilines derived from dehydroabietic acid, the main component of disproportionated rosin, are presented. The redox properties of the new diarylamines were investigated by cyclic voltammetry, and their free radical scavenging activity was tested by reduction of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Three of the diarylamines with lower oxidation potential proved to be as active as isopropyldiphenylamine (IPPD) and superior to tert-butylhydroxytoluene (BHT), both commercially available synthetic antioxidants.