(4aR,9R,10R,10aS)-1,3,4,9,10,10a-六氢-5,6,10-三羟基-1,1-二甲基-7-(1-甲基乙基)-2H-9,4a-(环氧甲烷)菲-12-酮 | 93780-80-4

• 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
• 中文名称: (4aR,9R,10R,10aS)-1,3,4,9,10,10a-六氢-5,6,10-三羟基-1,1-二甲基-7-(1-甲基乙基)-2H-9,4a-(环氧甲烷)菲-12-酮
• 中文别名: 异迷迭香酚
• 英文名称: isorosmanol
• 英文别名: (1R,8R,9R,10S)-3,4,9-trihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• CAS: 93780-80-4
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: UXVPWKDITRJELA-CLWJZODNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,9R,10R,10aS)-1,3,4,9,10,10a-六氢-5,6,10-三羟基-1,1-二甲基-7-(1-甲基乙基)-2H-9,4a-(环氧甲烷)菲-12-酮 在 咪唑 、 4-二甲氨基吡啶 、 碘苯二乙酸 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Biomimetic Synthesis of Isorosmanol and Przewalskin A

  摘要：

  Przewalskin A, a novel C-23 terpenoid with anti-HIV-1 activity from Salvia przewalskii Maxim, was formed in 10 steps via isorosmanol from (+)-carnosic acid. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by epoxidation, epoxide ring opening, and lactonization in one pot to prepare the 11,12-dimethoxy isorosmanol, and bismuthonium ylide-induced ring expansion of o-quinone to construct the 2-aryl-3-hydroxytropone.

  DOI：

  10.1021/acs.joc.7b02369
• 作为产物：
  描述：

  11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester 在 三溴化硼 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.67h， 生成 (4aR,9R,10R,10aS)-1,3,4,9,10,10a-六氢-5,6,10-三羟基-1,1-二甲基-7-(1-甲基乙基)-2H-9,4a-(环氧甲烷)菲-12-酮
  参考文献：
  名称：

  Biomimetic Synthesis of Isorosmanol and Przewalskin A

  摘要：

  Przewalskin A, a novel C-23 terpenoid with anti-HIV-1 activity from Salvia przewalskii Maxim, was formed in 10 steps via isorosmanol from (+)-carnosic acid. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by epoxidation, epoxide ring opening, and lactonization in one pot to prepare the 11,12-dimethoxy isorosmanol, and bismuthonium ylide-induced ring expansion of o-quinone to construct the 2-aryl-3-hydroxytropone.

  DOI：

  10.1021/acs.joc.7b02369

文献信息

• Semisynthesis and Biological Evaluation of Abietane-Type Diterpenes. Revision of the Structure of Rosmaquinone
  作者：Joaquín G. Marrero、Laila Moujir、Lucía S. Andrés、Nayely P. Montaño、Liliana Araujo、Javier G. Luis

  DOI：10.1021/np900047p

  日期：2009.8.28

  isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities.

  新的芳族二萜7β- ø -benzylrosmanol（3），7β- Ô苄基-11,12-二- Ö -methylrosmanol（4），和7α-thiophenylcarnosic酸（5）已经由从鼠尾草酚部分合成得到的（1），丹参物种中存在丰富的天然二萜。这些化合物的结构是根据其物理和光谱数据确定的。已知的二萜sagequinone甲基化物A（6），7β- Ô -methylrosmanol（7），7- Ô -methylrosmanol（8），和rosmaquinone B（9）来自rosmanol（2）。这些半合成二萜的光谱数据与文献报道的数据相同。另外，新的半合成异松香醌（10）是从异松香醇（12）获得的。根据2D NMR光谱重新分配了rosmaquinone（11）的质子共振。评价了这些化合物以及八种已知的类似物的细胞毒性和抗菌活性。
• Nakatani, Nobuji; Inatani, Reiko, Agricultural and Biological Chemistry, 1984, vol. 48, # 8, p. 2081 - 2086
  作者：Nakatani, Nobuji、Inatani, Reiko

  DOI：——

  日期：——
• Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues
  作者：Yutaka Aoyagi、Yoshinao Takahashi、Yudai Satake、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto、Teruo Kurihara

  DOI：10.1016/j.bmc.2006.03.047

  日期：2006.8

  Seven known abietane diterpenoids and 11-O- and 12-O-acetylcarnosic acids were isolated from a methanol extract of Perovskia abrotanoides (Labiatae). Structure and cytotoxic activity relationships (SARs) of the natural and semisynthetic analogues of the presently isolated abietane diterpenoids were studied by using P388 murine leukemia cells. (c) 2006 Elsevier Ltd. All rights reserved.
• KELECOM, A.;BRASIL, MEDEIROS W. L., AN. ACAD. BRAS. CIENC., 58,(1986) N 3, 369-374
  作者：KELECOM, A.、BRASIL, MEDEIROS W. L.

  DOI：——

  日期：——
• Synergistic pharmaceutical compositions useful in prevention and treatment of beta-amyloid protein-induced disease
  申请人：Kim S. H. L. Darrick

  公开号：US20070003641A1

  公开（公告）日：2007-01-04

  Disclosed are combinations of natural and synthetic turmeric, ginger, ginko biloba, sage, and rosemary compounds suitable for treatment of beta-amyloid-disease induced disease that have synergistic anti-βA peptide effects when members of the five groups of compounds are combined. Suitable members of the compounds include both natural compounds derived from extracts of each of Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., or Rosmarinus sp. as well as synthetic homologues and analogues of such natural compounds. Sage and rosemary derived compounds suitable alone for treatment of beta-amyloid induced disease is also described.