(3S,4aR,4bS,8aS,10aR)-3-hydroxy-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthrene-1-carbaldehyde | 1186505-13-4

• 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
• 英文名称: (3S,4aR,4bS,8aS,10aR)-3-hydroxy-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthrene-1-carbaldehyde
• CAS: 1186505-13-4
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: OGDHOMYUOVVEDQ-TXTPUJOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4aR,4bS,8aS,10aR)-3-hydroxy-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthrene-1-carbaldehyde 在 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 12.67h， 生成 (3R,4aR,4bS,8aS,10aR)-2,4b,8,8,10a-pentamethyl-1-vinyl-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-3-ol
  参考文献：
  名称：

  海洋酯类酯，16-脱乙酰氧基-scalarafuran，（+）-scalarolide及其类似物的立体选择性合成

  摘要：

  描述了立体选择性合成的C12氧化的海洋scalaranic sesterterpenes 16-deacetoxy-scalarafuran，（+）-scalarolide及其非天然类似物。它们的合成涉及三个关键的转变，即环氧化物的开环重排，立体选择性Diels-Alder加成和一锅γ-丁烯醇内酯形成过程，以及天然（+）-scalarolide和16-脱乙酰氧基的绝对构型证实了-scalarafuran。

  DOI：

  10.1016/j.tet.2011.05.092
• 作为产物：
  描述：

  (1R,2S,7S,10R,11S,12R,14S)-2,6,6,10,12-pentamethyl-13-oxatetracyclo[8.5.0.02,7.012,14]pentadecane-11-carbaldehyde 在 四氢吡咯 作用下， 以 乙醚 为溶剂， 以93%的产率得到(3S,4aR,4bS,8aS,10aR)-3-hydroxy-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthrene-1-carbaldehyde
  参考文献：
  名称：

  The first synthesis of marine sesterterpene (+)-scalarolide

  摘要：

  The synthesis of the first example of C12 oxygenated marine scalaranic sesterterpenes (+)-scalarolide was achieved through three key steps including the ring-opening rearrangement of epoxide, stereoselective Diels-Alder addition and one-pot gamma-butenolide formation process, and the absolute configuration of natural scalarolide was confirmed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.064

文献信息

• An Alternative Approach towards C-12 Functionalized Scalaranic Sesterterpenoids Synthesis of 17-Oxo-20-norscalaran-12α,19-O-lactone
  作者：Olga Morarescu、Marina Grinco、Veaceslav Kulciţki、Sergiu Shova、Nicon Ungur

  DOI：10.3390/md19110636

  日期：——

  extensively from marine sponges and shell-less mollusks. Some representatives were also reported recently from superior plants. Many scalarane sesterterpenoids displayed a wide spectrum of valuable properties, such as antifeedant, antimicrobial, antifungal, antitubercular, antitumor, anti-HIV properties, cytotoxicity and stimulation of nerve growth factor synthesis, as well as anti-inflammatory activity. Due

  Scalarane sesterterpenoids 作为有趣的生物活性天然产物出现，从海绵和无壳软体动物中广泛分离。最近还报道了一些代表来自上等植物。许多scalarane sesterterpenoids表现出广泛的有价值的特性，例如拒食、抗菌、抗真菌、抗结核、抗肿瘤、抗HIV特性、细胞毒性和刺激神经生长因子合成，以及抗炎活性。由于它们重要的生物学特性，人们对天然scalaranes的化学合成进行了许多努力。主要的合成挑战与其复杂的多环框架、手性中心和不同的官能团有关，特别是 C-12 位的含氧官能团，这是许多研究的scalaranes生物活性的先决条件。目前的工作解决了这个问题和17-oxo-20-norscalaran-12α,19-的合成描述了O-内酯。它是通过从 (-)-sclareol 获得的 12α- hydroxy- ent -isocopal-13(14)-en-15-al
• Stereoselective synthesis of marine sesterterpenes, 16-deacetoxy-scalarafuran, (+)-scalarolide and their analogs
  作者：Wen-Yuan Fan、Zheng-Lin Wang、Zi-Gang Zhang、Hong-Chang Li、Wei-Ping Deng

  DOI：10.1016/j.tet.2011.05.092

  日期：2011.8

  The stereoselective synthesis of C12 oxygenated marine scalaranic sesterterpenes 16-deacetoxy-scalarafuran, (+)-scalarolide and their unnatural analogs were described. Three key transformations were involved in their synthesis, which are the ring-opening rearrangement of epoxide, stereoselective Diels–Alder addition, and one-pot γ-butenolide formation process, and the absolute configurations of natural

  描述了立体选择性合成的C12氧化的海洋scalaranic sesterterpenes 16-deacetoxy-scalarafuran，（+）-scalarolide及其非天然类似物。它们的合成涉及三个关键的转变，即环氧化物的开环重排，立体选择性Diels-Alder加成和一锅γ-丁烯醇内酯形成过程，以及天然（+）-scalarolide和16-脱乙酰氧基的绝对构型证实了-scalarafuran。
• The first synthesis of marine sesterterpene (+)-scalarolide
  作者：Xiang-Jian Meng、Yang Liu、Wen-Yuan Fan、Bin Hu、Wenting Du、Wei-Ping Deng

  DOI：10.1016/j.tetlet.2009.06.064

  日期：2009.9

  The synthesis of the first example of C12 oxygenated marine scalaranic sesterterpenes (+)-scalarolide was achieved through three key steps including the ring-opening rearrangement of epoxide, stereoselective Diels-Alder addition and one-pot gamma-butenolide formation process, and the absolute configuration of natural scalarolide was confirmed. (C) 2009 Elsevier Ltd. All rights reserved.