[(1R,2R,3S,4S,4aR,8R,8aS)-4-[(3aS,5S,6aS)-3a-hydroxy-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-5-yl]-1-hydroxy-3,4,8a-trimethyl-5-oxospiro[1,2,3,4a,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (E)-3-phenylprop-2-enoate | 211425-17-1

• 分子结构分类: 有机化合物
• 英文名称: [(1R,2R,3S,4S,4aR,8R,8aS)-4-[(3aS,5S,6aS)-3a-hydroxy-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-5-yl]-1-hydroxy-3,4,8a-trimethyl-5-oxospiro[1,2,3,4a,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (E)-3-phenylprop-2-enoate
• CAS: 211425-17-1
• 化学式: C₂₉H₃₆O₈
• 分子量: 512.6
• InChiKey: YKUHAAYSNIFPRW-SJLASXSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 [(1R,2R,3S,4S,4aR,8R,8aS)-4-[(3aS,5S,6aS)-3a-hydroxy-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-5-yl]-1-hydroxy-3,4,8a-trimethyl-5-oxospiro[1,2,3,4a,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (E)-3-phenylprop-2-enoate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以4.4 mg的产率得到
  参考文献：
  名称：

  Studies on Nepalese Crude Drugs. XXIV. Diterpenoid Constituents of the Leaves of Scutellaria repens BUCH.-HAM. ex D. DON.

  摘要：

  From the leaves of Scutellaria repens, sixteen new neoclerodane-type diterpenes named scuterepenins A1, A2, B, C1, C2, D1, D2, E, F1, F2, G1 and G2, and scuterepenosides A1, A2, A3 and A4, have been isolated along with a new 9, 11-secoabietane-type diterpene named scuterepenin H. The structures of these compounds have been determined by spectroscopic and chemical methods as follows : scuterepenin A1, (4R, 11S, 13R)-7β-trans-cinnamoyloxy-4, 6α, 13, 18-tetrahydroxy-11, 16 : 15, 16-diepoxy-1-neoclerodanone; scuterepenin A2, cis-cinnamoyl form of A1; scuterepenin B, (4R, 11S, 13R)-7β-trans-cinnamoyloxy-2α, 4, 6α, 13, 18-pentahydroxy-11, 16 : 15, 16-diepoxy-1-neocler-odanone; scuterepenin C1, (4R, 11S, 13R)-6α-trans-cinnamoyloxy-7β, 13-dihydroxy-4, 18 : 11, 16 : 15, 16-triepoxy-1-neoclerodanone; scuterepenin C2, cis-cinnamoyl form of C1; scuterepenin D1, (4R, 11S*, 13R*)-6α-trans-cinnamoyl-oxy-1β, 7β-diacetoxy-11, 16 : 15, 16-diepoxy-18-neoclerodanal; scuterepenin D2, cis-cinnamoyl form of D1; scuterepenin E, (4R, 11S*, 13R*)-1β-acetoxy-7β-trans-cinnamoyloxy-6α-hydroxy-11, 16 : 15, 16-diepoxy-18-neoclerodanal; scuterepenin F1, (4R, 11S*, 13R*)-1β-O-acetyl-7β-O-trans-cinnamoyl-18β-O-methyl-6α, 18 : 11, 16 : 15, 16-triepoxyneoclerodane-1, 7, 18-triol; scuterepenin F2, cis-cinnamoyl form of F1; scuterepenin G1, (4R, 7R, 11S, 13R)-6α-O-trans-cinnamoyl-1, 16 : 4, 18 : 11, 16-triepoxyneoclerodane-6, 7, 15-triol; scuterepenin G2, cis-cinnamoyl form of G1; scuterepenoside A1, (4R, 13S*, 16S*)-1β-trans-cinnamoyloxy-6α-(β-D-glucopyranosyloxy)-16-methoxy-15, 16-epoxy-18-neoclerodanal; scuterepenoside A2, cis-cinnamoyl form of A1; scuterepenoside A3, (13S*, 16R*)-form of A1; scuterepenoside A4, (13S*, 16R*)-form of A2; scuterepenin H, (5S, 10R, 13S, 14S)-13-hydroxy-7-oxo-9, 11-seco-8-abieten-14, 11-olide.

  DOI：

  10.1248/cpb.46.988
• 作为产物：
  描述：

  (E)-3-Phenyl-acrylic acid (1R,2R,3S,4S,4aR,8R,8aS)-1,8-dihydroxy-4-((2S,3aS,6aS)-3a-hydroxy-hexahydro-furo[2,3-b]furan-2-yl)-8-hydroxymethyl-3,4,8a-trimethyl-5-oxo-decahydro-naphthalen-2-yl ester 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以18 mg的产率得到[(1R,2R,3S,4S,4aR,8R,8aS)-4-[(3aS,5S,6aS)-3a-hydroxy-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-5-yl]-1-hydroxy-3,4,8a-trimethyl-5-oxospiro[1,2,3,4a,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Studies on Nepalese Crude Drugs. XXIV. Diterpenoid Constituents of the Leaves of Scutellaria repens BUCH.-HAM. ex D. DON.

  摘要：

  From the leaves of Scutellaria repens, sixteen new neoclerodane-type diterpenes named scuterepenins A1, A2, B, C1, C2, D1, D2, E, F1, F2, G1 and G2, and scuterepenosides A1, A2, A3 and A4, have been isolated along with a new 9, 11-secoabietane-type diterpene named scuterepenin H. The structures of these compounds have been determined by spectroscopic and chemical methods as follows : scuterepenin A1, (4R, 11S, 13R)-7β-trans-cinnamoyloxy-4, 6α, 13, 18-tetrahydroxy-11, 16 : 15, 16-diepoxy-1-neoclerodanone; scuterepenin A2, cis-cinnamoyl form of A1; scuterepenin B, (4R, 11S, 13R)-7β-trans-cinnamoyloxy-2α, 4, 6α, 13, 18-pentahydroxy-11, 16 : 15, 16-diepoxy-1-neocler-odanone; scuterepenin C1, (4R, 11S, 13R)-6α-trans-cinnamoyloxy-7β, 13-dihydroxy-4, 18 : 11, 16 : 15, 16-triepoxy-1-neoclerodanone; scuterepenin C2, cis-cinnamoyl form of C1; scuterepenin D1, (4R, 11S*, 13R*)-6α-trans-cinnamoyl-oxy-1β, 7β-diacetoxy-11, 16 : 15, 16-diepoxy-18-neoclerodanal; scuterepenin D2, cis-cinnamoyl form of D1; scuterepenin E, (4R, 11S*, 13R*)-1β-acetoxy-7β-trans-cinnamoyloxy-6α-hydroxy-11, 16 : 15, 16-diepoxy-18-neoclerodanal; scuterepenin F1, (4R, 11S*, 13R*)-1β-O-acetyl-7β-O-trans-cinnamoyl-18β-O-methyl-6α, 18 : 11, 16 : 15, 16-triepoxyneoclerodane-1, 7, 18-triol; scuterepenin F2, cis-cinnamoyl form of F1; scuterepenin G1, (4R, 7R, 11S, 13R)-6α-O-trans-cinnamoyl-1, 16 : 4, 18 : 11, 16-triepoxyneoclerodane-6, 7, 15-triol; scuterepenin G2, cis-cinnamoyl form of G1; scuterepenoside A1, (4R, 13S*, 16S*)-1β-trans-cinnamoyloxy-6α-(β-D-glucopyranosyloxy)-16-methoxy-15, 16-epoxy-18-neoclerodanal; scuterepenoside A2, cis-cinnamoyl form of A1; scuterepenoside A3, (13S*, 16R*)-form of A1; scuterepenoside A4, (13S*, 16R*)-form of A2; scuterepenin H, (5S, 10R, 13S, 14S)-13-hydroxy-7-oxo-9, 11-seco-8-abieten-14, 11-olide.

  DOI：

  10.1248/cpb.46.988