5β,10α-14,15,Dinor-8-labden-13-on | 74111-47-0

• 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: 5β,10α-14,15,Dinor-8-labden-13-on
• 英文别名: 14,15-bisnor-(5R,10R)-8(9)-labdaen-13-one；ent-14,15-bisnorlabd-8-en-13-one；4-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]butan-2-one
• CAS: 74111-47-0
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: FYTVLSLHXKPOEQ-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5β,10α-14,15,Dinor-8-labden-13-on 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 sodium hydride 、 二异丁基氢化铝 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.17h， 生成
  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
• 作为产物：
  描述：

  (E,Z)-ent-8-acetoxylabd-13-ene 在 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 176.0h， 生成 5β,10α-14,15,Dinor-8-labden-13-on
  参考文献：
  名称：

  Dawson, Raymond M.; Godfrey, Ian M.; Hogg, Ronald W., Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 561 - 580

  摘要：

  DOI：

文献信息

• Photochemische Reaktionen. 106. Mitteilung. Zur Photochemie tetraalkylsubstituierter ?-Keto-olefine
  作者：Jacob Berger、Michikazu Yoshioka、Markus P. Zink、Hans R. Wolf、Oskar Jeger

  DOI：10.1002/hlca.19800630116

  日期：1980.1.23

  The Photochemistry of Tetraalkyl Substituted γ-Keto-olefines

  四烷基取代的γ-酮烯烃的光化学
• DAWSON, RAYMOND M.;GODIREY, IAN M.;HOGG, RONALD W.;KNOX, JOHN R., AUSTRAL. J. CHEM., 42,(1989) N, C. 561-579
  作者：DAWSON, RAYMOND M.、GODIREY, IAN M.、HOGG, RONALD W.、KNOX, JOHN R.

  DOI：——

  日期：——
• Dawson, Raymond M.; Godfrey, Ian M.; Hogg, Ronald W., Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 561 - 580
  作者：Dawson, Raymond M.、Godfrey, Ian M.、Hogg, Ronald W.、Knox, John R.

  DOI：——

  日期：——
• 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.