[3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1Η-naphtho[2,1-b]pyran | 27642-41-7

• 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: [3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1Η-naphtho[2,1-b]pyran
• 英文别名: [3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran；(-)-ent-13-epi-manoyl oxide；13-epi-ent.-manoyl oxide；ent-13-epi manoyl oxide；ent-13-epi-manoyl oxide；ent-13-epi-manoyloxide；(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene
• CAS: 27642-41-7
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: IGGWKHQYMAJOHK-QVHQYWGISA-N

物化性质

• 熔点：
  135-137 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  338.6±11.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1Η-naphtho[2,1-b]pyran 在 氨 、 lithium 作用下， 生成 (1S,2S,4aR,8aR)-2,5,5,8a-Tetramethyl-1-((E)-3-methyl-pent-3-enyl)-decahydro-naphthalen-2-ol
  参考文献：
  名称：

  Jefferies,P.R.; Payne,T.G., Australian Journal of Chemistry, 1965, vol. 18, p. 1441 - 1450

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R,4aS,6aR,10aR,10bS)-3,4a,7,7,10a-Pentamethyl-3-vinyl-decahydro-benzo[f]chromen-9-one 以90 mg的产率得到[3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1Η-naphtho[2,1-b]pyran
  参考文献：
  名称：

  Ent-2α-hydroxy-13-epi-manoyl oxide from Sideritis perfoliata

  摘要：

  DOI：

  10.1016/s0031-9422(00)80713-x

文献信息

• Brominative cyclisation of nerolidol and geranyl-linalool
  作者：Tadahiro Kato、Koichi Ishii、Isao Ichinose、Yoko Nakai、Takashi Kumagai

  DOI：10.1039/c39800001106

  日期：——

  (+)-Nerolidol was treated with 2,4,4,6-tetrabromocyclohexa-2,5-dienone to afford the brominative cyclisation products α- and β-snyderols and 3-bromocaparrapi oxide and its 8-epimer; (±)-geranyl-linalool gave the analogous tricyclic ethers.

  用2,4,4,6-四溴环己-2,5-二烯酮处理（+）-Nerolidol，得到溴化环化产物α-和β-炔诺醇和3-溴己酸环己酯及其8-末端。（±）-香叶基-芳樟醇得到类似的三环醚。
• Efficient heterocyclisation by (di)terpene synthases
  作者：S. Mafu、K. C. Potter、M. L. Hillwig、S. Schulte、J. Criswell、R. J. Peters

  DOI：10.1039/c5cc05754j

  日期：——

  Ability of (di)terpene synthases to catalyse heterocyclization indicated by the ease that this is accomplished by widely divergent ent-kaurene synthases.

  (二萜)合酶催化杂环化的能力是由广泛不同的ent-考鲁烯合酶轻松完成的。
• Functional divergence of diterpene syntheses in the medicinal plant Salvia miltiorrhiza Bunge
  作者：Guanghong Cui、Lixin Duan、Baolong Jin、Jun Qian、Zheyong Xue、Guoan Shen、John, Hugh Snyder、Jingyuan Song、Shilin Chen、Luqi Huang、Reuben, J. Peters、Xiaoquan Qi

  DOI：10.1104/pp.15.00695

  日期：——

  The medicinal plant Salvia miltiorrhiza produces various tanshinone diterpenoids that have pharmacological activities such as vasorelaxation against ischemia reperfusion injury and antiarrhythmic effects. Their biosynthesis is initiated from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate by sequential reactions catalyzed by copalyl diphosphate synthase (CPS) and kaurene synthase-like cyclases. Here, we report characterization of these enzymatic families from S. miltiorrhiza, which has led to the identification of unique pathways, including roles for separate CPSs in tanshinone production in roots versus aerial tissues (SmCPS1 and SmCPS2, respectively) as well as the unique production of ent-13-epi-manoyl oxide by SmCPS4 and S. miltiorrhiza kaurene synthase-like2 in floral sepals. The conserved SmCPS5 is involved in gibberellin plant hormone biosynthesis. Down-regulation of SmCPS1 by RNA interference resulted in substantial reduction of tanshinones, and metabolomics analysis revealed 21 potential intermediates, indicating a complex network for tanshinone metabolism defined by certain key biosynthetic steps. Notably, the correlation between conservation pattern and stereochemical product outcome of the CPSs observed here suggests a degree of correlation that, especially when combined with the identity of certain key residues, may be predictive. Accordingly, this study provides molecular insights into the evolutionary diversification of functional diterpenoids in plants.

  药用植物丹参（Salvia miltiorrhiza）可产生多种具有药理活性的丹参酮二萜类化合物，如抗缺血再灌注损伤的血管舒张作用和抗心律失常作用。它们的生物合成由一般二萜类化合物前体（E,E,E）-二磷酸二烯丙基二烯丙基二磷酸开始，通过由二磷酸二萜烯基合成酶（CPS）和类贝壳杉烯合成酶环化酶催化的一系列反应进行。在此，我们报告了丹参中这些酶家族的表征，从而确定了独特的途径，包括在根和地上组织中丹参酮产生的不同CPS的作用（分别为SmCPS1和SmCPS2），以及SmCPS4和丹参类贝壳杉烯合成酶-like2在花萼中产生的ent-13-epi-manoyl oxide。保守的SmCPS5参与赤霉素植物激素的生物合成。通过RNA干扰下调SmCPS1导致丹参酮的显著减少，代谢组学分析揭示了21种潜在中间体，表明丹参酮代谢由某些关键生物合成步骤定义的复杂网络。值得注意的是，此处观察到的CPS的保守模式与立体化学产物结果之间的相关性表明，当与某些关键残基的识别相结合时，可能具有预测性。因此，这项研究为
• ALCARAZ, M. J.;GARCIA-OCHOA, S.;JIMENEZ, M. J.;VALVERDE, S.;VILLAR, A., PHYTOCHEMISTRY, 28,(1989) N, C. 1267-1268
  作者：ALCARAZ, M. J.、GARCIA-OCHOA, S.、JIMENEZ, M. J.、VALVERDE, S.、VILLAR, A.

  DOI：——

  日期：——
• Jefferies,P.R.; Payne,T.G., Australian Journal of Chemistry, 1965, vol. 18, p. 1441 - 1450
  作者：Jefferies,P.R.、Payne,T.G.

  DOI：——

  日期：——