(+)-1,2,4-trimethoxy-3-[(5'S,10'S)-8'(9')-drimen-11'-yl]benzene | 166406-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+)-1,2,4-trimethoxy-3-[(5'S,10'S)-8'(9')-drimen-11'-yl]benzene
• 英文别名: (4aS,8aS)-4,4,7,8a-tetramethyl-8-[(2,3,6-trimethoxyphenyl)methyl]-1,2,3,4a,5,6-hexahydronaphthalene
• CAS: 166406-79-7
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: FBIYUEFEHSMBAS-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-1,2,4-trimethoxy-3-[(5'S,10'S)-8'(9')-drimen-11'-yl]benzene 在 碘代三甲硅烷 作用下， 以 吡啶 为溶剂， 以23%的产率得到2-Methoxy-3-((4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol
  参考文献：
  名称：

  An Efficient Synthesis of Wiedendiol-A from (+)-Sclareolide

  摘要：

  An efficient synthesis of Wiedendiol-A (1) is described starting from commercially available (+)-sclareolide. This synthesis also confirms the absolute stereochemistry of Wiedendiol-A.

  DOI：

  10.1016/00404-0399(50)1023b-
• 作为产物：
  描述：

  (+)-Bicyclofarnesol 在 吡啶 、 四甲基乙二胺 、 叔丁基锂 、 三溴化磷 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 1.67h， 生成 (+)-1,2,4-trimethoxy-3-[(5'S,10'S)-8'(9')-drimen-11'-yl]benzene
  参考文献：
  名称：

  Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)-norsesterterpene diene ester and (−)-subersic acid

  摘要：

  Both enantiomers (8aR)-7 and (8aS)-7 of bicyclofarnesol were synthesized from the enzymatic resolution products (1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-5 (98% ee) and acetate of(1S,4aS, 8aS)-1,2,3,4,4a, 5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aS)-6 (> 99% ee), respectively. The formal synthesis of (+)-wiedendiol 1 was achieved via a coupling reaction of an ate complex derived from 1,2,4-trimethoxybenzene with allyl bromide (8aS)-8 derived from (8aS)-7. The total synthesis of (+)-norsesterterpene diene ester 2 was achieved, based on the synthesis of (13E,10S)-alpha,beta-unsaturated aldehyde 12, derived from (8aS)-7, followed by the selective construction of the (3E,5E)-diene moiety including a C(2)-stereogenic centre in (+)-2. The total synthesis of (-)-subersic acid 3 was carried out based on a Stille coupling between allyl trifluoroacetate congener 25c, derived from (8aR)-7, corresponding to the diterpene part, and aryl stannane congener 26 in the presence of Pd catalyst and CuI as an additive. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.010

文献信息

• Natural product synthesis from (8aR)- and (8aS)-bicyclofarnesols: synthesis of (+)-wiedendiol A, (+)-norsesterterpene diene ester and (−)-subersic acid
  作者：Yuusuke Arima、Masako Kinoshita、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2007.07.010

  日期：2007.7

  Both enantiomers (8aR)-7 and (8aS)-7 of bicyclofarnesol were synthesized from the enzymatic resolution products (1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-5 (98% ee) and acetate of(1S,4aS, 8aS)-1,2,3,4,4a, 5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aS)-6 (> 99% ee), respectively. The formal synthesis of (+)-wiedendiol 1 was achieved via a coupling reaction of an ate complex derived from 1,2,4-trimethoxybenzene with allyl bromide (8aS)-8 derived from (8aS)-7. The total synthesis of (+)-norsesterterpene diene ester 2 was achieved, based on the synthesis of (13E,10S)-alpha,beta-unsaturated aldehyde 12, derived from (8aS)-7, followed by the selective construction of the (3E,5E)-diene moiety including a C(2)-stereogenic centre in (+)-2. The total synthesis of (-)-subersic acid 3 was carried out based on a Stille coupling between allyl trifluoroacetate congener 25c, derived from (8aR)-7, corresponding to the diterpene part, and aryl stannane congener 26 in the presence of Pd catalyst and CuI as an additive. (c) 2007 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of Wiedendiol-A from (+)-Sclareolide
  作者：S Chackalamannil

  DOI：10.1016/00404-0399(50)1023b-

  日期：1995.7.24

  An efficient synthesis of Wiedendiol-A (1) is described starting from commercially available (+)-sclareolide. This synthesis also confirms the absolute stereochemistry of Wiedendiol-A.