(5'aS,3R,5S)-5-(3-呋喃基)-3',4,4',5,5',5'a,7',8'-八氢-7'alpha-甲基螺[呋喃-3(2H),6'-[6H]萘并[1,8-bc]呋喃]-2-酮 | 68370-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: (5'aS,3R,5S)-5-(3-呋喃基)-3',4,4',5,5',5'a,7',8'-八氢-7'alpha-甲基螺[呋喃-3(2H),6'-[6H]萘并[1,8-bc]呋喃]-2-酮
• 英文名称: montanin A
• 英文别名: (5'S,8S,9R,10R)-5'-(furan-3-yl)-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodeca-1(12),3-diene-9,3'-oxolane]-2'-one
• CAS: 68370-49-0
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: CZGWUKXZLUIKBU-IUYNRSMJSA-N

物化性质

• 熔点：
  126-127 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  499.0±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5'aS,3R,5S)-5-(3-呋喃基)-3',4,4',5,5',5'a,7',8'-八氢-7'alpha-甲基螺[呋喃-3(2H),6'-[6H]萘并[1,8-bc]呋喃]-2-酮 以 氯仿 为溶剂， 反应 120.0h， 以30 mg的产率得到山藿香素
  参考文献：
  名称：

  从一些克罗二萜类化合物的绝对立体香科科属种

  摘要：

  X射线分析确定了19-乙酰基萘酚和另一种来自T. gnaphalodes的二萜类化合物的绝对构型，该构型可能与teucrin P 1相同。它们属于新环戊烷系列。异黄酮还被证明属于该系列。

  DOI：

  10.1039/p19810001186
• 作为产物：
  描述：

  (3R,5S,5'R,8'abeta)-4'aalpha-乙酰氧基甲基-5-(3-呋喃基)-2',3',4,5,6',7',8',8'alpha-八氢-2'alpha-甲基二螺[呋喃-3(2H),1'(5'H)-萘-5',2''-环氧乙烷]-2,4'(4'aH)-二酮 在 氢氧化钾 作用下， 反应 0.25h， 以150 mg的产率得到(5'aS,3R,5S)-5-(3-呋喃基)-3',4,4',5,5',5'a,7',8'-八氢-7'alpha-甲基螺[呋喃-3(2H),6'-[6H]萘并[1,8-bc]呋喃]-2-酮
  参考文献：
  名称：

  从一些克罗二萜类化合物的绝对立体香科科属种

  摘要：

  X射线分析确定了19-乙酰基萘酚和另一种来自T. gnaphalodes的二萜类化合物的绝对构型，该构型可能与teucrin P 1相同。它们属于新环戊烷系列。异黄酮还被证明属于该系列。

  DOI：

  10.1039/p19810001186

文献信息

• Total syntheses of (±)-montanin A and (±)-teuscorolide
  作者：I-Chia Chen、Yen-Ku Wu、Hsing-Jang Liu、Jiang-Liang Zhu

  DOI：10.1039/b807218c

  日期：——

  The first total syntheses of (±)-montanin A and (±)-teuscorolide have been achieved from an advanced precursor previously developed via a Diels–Alder strategy; in the synthetic sequence, the synthesis of montanin A was first accomplished in 8 steps, from which teuscorolide was readily achieved in 2 steps by using a novel furan oxidative cyclization–retro-cyclization process as a key operation.

  (±)-montanin A 和 (±)-teuscorolide 的首次全合成是由先前通过 Diels-Alder 策略开发的先进前体实现的；在合成过程中，首先通过8步完成了montanin A的合成，然后以新型呋喃氧化环化-逆环化工艺为关键操作，通过2步轻松合成了teuscorolide。
• Neo-clerodane diterpenoids from Teucrium corymbosum
  作者：Maurizio Bruno、Caterina Fazio、Franco Piozzi、Benjamín Rodríguez、María C. de la Torre

  DOI：10.1016/0031-9422(95)00519-d

  日期：1995.11

  Abstract A novel 19-nor-neo-clerodane derivative, teucorymbin, and three known neo-clerodanes (19-acetylgnaphalin, teucjaponin A and 6-acetylteucjaponin B) were isolated from the aerial parts of Teucrium corymbosum . The structure of teucorymbin [18-acetoxy-15,16-epoxy-6-oxo-19-nor-neo-cleroda-4,13(16),14-trien-20,12 S -olide] was established by chemical and spectroscopic means.

  摘要 从 Teucrium corymbosum 的地上部分分离出一种新的 19-nor-neo-clerodane 衍生物 teucorymbin 和三种已知的新 clerodanes（19-acetylgnaphalin、teucjaponin A 和 6-acetylteucjaponin B）。teucorymbin [18-acetoxy-15,16-epoxy-6-oxo-19-nor-neo-cleroda-4,13(16),14-trien-20,12 S-olide]的结构是通过化学和光谱手段。
• Enantioselective and collective total synthesis of pentacyclic 19-<i>nor</i>-clerodanes
  作者：Zhi-Mao Zhang、Junliang Zhang、Quan Cai

  DOI：10.1039/d3sc04335e

  日期：——

  total synthesis of seven pentacyclic 19-nor-clerodane diterpenoids, namely (+)-teucvin (+)-cracroson A, (+)-cracroson E, (+)-montanin A, (+)-teucvisin C, (+)-teucrin A, and (+)-2-hydroxyteuscorolide. An ytterbium-catalyzed asymmetric inverse-electron-demand Diels–Alder reaction of 4-methyl-2-pyrone with a chiral C5-substituted cyclohexa-1,3-dienol silyl ether is the key feature of the synthesis, which

  我们在此报道了七种五环 19- nor -clerodane 二萜类化合物的集体不对称全合成，即 (+)-teucvin (+)-cracroson A、(+)-cracroson E、(+)-montanin A、(+)-teucvisin C、(+)-teucrin A 和 (+)-2-羟基 teuscorolide。镱催化的 4-甲基-2-吡喃酮与手性 C5 取代的环己-1,3-二烯醇甲硅烷基醚的不对称逆电子需求狄尔斯-阿尔德反应是该合成的关键特征，它提供了常见的顺式反应-十氢化萘中间体，具有五个连续立体中心，具有优异的产率和立体选择性。从这种多样化的中间体，分别通过十三步和十八步实现了(+)-teucvin和(+)-2-羟基teuscorolide的全合成。通过后期氧化态调整，从 (+)-teucvin 衍生出另外五种五环 19- nor -clerodanes。
• Transformation of montanin A into isocrotocaudin. A revision of the structures of crotocaudin and isocrotocaudin
  作者：Ana Lourenço、María C. de la Torre、Benjamín Rodríguez

  DOI：10.1016/0040-4039(91)80505-z

  日期：1991.12

  Starting from montanin A (3) compound 11 was obtained by opening of the C-20,C-12 gamma-lactone (6), oxidation of the C-12 hydroxyl group (9), relactonization to the beta, gamma-unsaturated gamma-lactone (10) via the C-12 enol form, and final selective air oxidation of the alpha,beta,beta'-trialkyl furan to the corresponding alpha,beta-unsaturated gamma-lactone (11). Compound 11 was identical to isocrotocaudin, to which structure 1 has previously been assigned only on spectroscopic grounds. The above transformation establishes that the previous 8S configuration of isocrotocaudin (1) and its related C-6,C-10 stereoisomer crotocaudin (2) must be corrected to 8R.
• Efficient Installation and Elaboration of C4-C6 fused Furan Moiety in the Total Synthesis of Teucrium Clerodane Diterpenoids
  作者：Jia-Liang Zhu、Hsing-Jang Liu、Yen-Ku Wu、I-Chia Chen

  DOI：10.3987/com-14-13045

  日期：——

  We previously reported the total synthesis of several Teucrium clerodane diterpenoids including teucvin (1), 12-epi-teucvin (2), montanin A (3) and teuscorolide (4) in a unified Diels-Alder approach. A full account for the tactical installation of the C4-C6 furan ring. of 3 from an alpha,beta-unsaturated lactone moiety, and the elaboration of the resulting furan unit into alpha,beta-unsaturated gamma-hydroxyl lactone for preparing 4 is discussed herein. In addition, the transformation of 3 and its 12-epimer into 1 and 2 by the air-mediated furan oxidation reaction is described.