(4R,6S,6aR,9S)-2-Methoxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol | 105519-39-9

• 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: (4R,6S,6aR,9S)-2-Methoxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol
• 英文别名: (4R,6S,6aR,9S)-2-methoxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol
• CAS: 105519-39-9
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: OMTFPXZGPBLHRI-DARAHFNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-D-xylopyranosyl trichloroacetimidate 、 (4R,6S,6aR,9S)-2-Methoxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(2S,3R,4S,5R)-2-(((3S,7R,9S,9aR)-5-methoxy-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  iso-PsE, a new pseudopterosin

  摘要：

  We describe the discovery of a new member of the pseudopterosin class of marine natural products. Its structure is isomeric with that of pseudopterosin E and has therefore been given the name iso-PsE. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.106
• 作为产物：
  描述：

  pseudopterosin C 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 (4R,6S,6aR,9S)-2-Methoxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol
  参考文献：
  名称：

  The pseudopterosins: a new class of antiinflammatory and analgesic diterpene pentosides from the marine sea whip Pseudopterogorgia elisabethae (Octocorallia)

  摘要：

  DOI：

  10.1021/jo00376a016

文献信息

• Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control
  作者：Srinivasarao Tenneti、Souvagya Biswas、Glen Adam Cox、Daniel J. Mans、Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/jacs.8b03549

  日期：2018.8.8

  with simple oxygenated styrene derivatives, we iteratively install the various exocyclic chiral centers present in typical serrulatane [e.g., a (+)- p-benzoquinone natural product, elisabethadione, nor-elisabethadione, helioporin D, a known advanced intermediate for the synthesis of colombiasin and elisapterosin] and amphilectane [e.g., A-F, G-J, and K,L pseudopterosins] derivatives. A concise table showing

  立构中心位于其所连接的环中手性碳旁边的环外位置，是许多生物活性天然产物中普遍存在的结构基序，包括二萜和三萜和类固醇。这些中心的安装一直是有机化学中长期存在的问题。很少有几类化合物比锯齿烷和两性烷更能说明这个问题，因为它们带有多个带有甲基的环外手性中心。乙烯基芳烃和 1,3-二烯（例如 1-乙烯基环烯烃）的镍催化不对称氢乙烯基化 (AHV) 提供了一种引入这些手性中心的极其简便的方法。本文记录了我们努力证明 AHV 的通用性，不仅可以获取天然产物，还可以获取其各种非对映异构衍生物。成功的关键是高度可调的亚磷酰胺 Ni(II) 配合物的可用性，可用于克服手性中间体固有的选择性。氢乙烯基化 (HV) 反应的产率非常好，所需异构体的选择性在 92-99% 范围内。新型、构型变化但空间要求较低的 2,2'-联苯酚衍生的亚磷酰胺 Ni 配合物（通过 X 射线完全表征）的发现对于几个 HV 反应的成功至
• Synthesis and an Evaluation of the Bioactivity of the <i>C</i>-Glycoside of Pseudopterosin A Methyl Ether
  作者：Wei Zhong、Claudia Moya、R. S. Jacobs、R. Daniel Little

  DOI：10.1021/jo801432t

  日期：2008.9.19

  The Suzuki-Miyaura cross-coupling protocol was applied to the synthesis of 1a, the C-glycoside analogue of PsA methyl ether. This marks the first construction of a C-glycoside for this class of marine natural products, thereby offering an opportunity to compare its bioactivity to the natural substances. Its activity profile resembled that of PsA (1) and PsA O-methyl ether (1b) when assayed for its anti-inflammatory activity and its ability to inhibit phagocytosis. We conclude that the intact structure is present when a pseudopterosin expresses its anti-inflammatory and phagocytosis inhibitory properties and that they are, therefore, not likely to be prodrugs. Results show that 1a is an effective binding agent toward the A(2A) and A(3) adenosine receptors, displaying IC50 values of 20 and 10 mu M, respectively.
• The pseudopterosins: a new class of antiinflammatory and analgesic diterpene pentosides from the marine sea whip Pseudopterogorgia elisabethae (Octocorallia)
  作者：Sally A. Look、William Fenical、Gayle K. Matsumoto、Jon Clardy

  DOI：10.1021/jo00376a016

  日期：1986.12
• iso-PsE, a new pseudopterosin
  作者：Christophe Hoarau、Daniel Day、Claudia Moya、Guang Wu、Abdul Hackim、Robert S. Jacobs、R. Daniel Little

  DOI：10.1016/j.tetlet.2008.05.106

  日期：2008.7

  We describe the discovery of a new member of the pseudopterosin class of marine natural products. Its structure is isomeric with that of pseudopterosin E and has therefore been given the name iso-PsE. (c) 2008 Elsevier Ltd. All rights reserved.