(-)-β-artemisia alcohol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-β-artemisia alcohol
• 英文别名: (-)-β-Artemisiaalkohol；(4R)-3,3,6-trimethylhepta-1,5-dien-4-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WPPVSYVQAKQNJK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-β-artemisia alcohol 在 溶剂黄146 、 铂 作用下， 生成 (-)-2,5,5-trimethyl-heptan-4-ol
  参考文献：
  名称：

  Takemoto; Nakajima, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 1307

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-3,3,6-trimethyl-1,5-heptadien-4-ol 4-acetate 在 氢氧化钾 作用下， 生成 (-)-β-artemisia alcohol
  参考文献：
  名称：

  Takemoto; Nakajima, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 1307

  摘要：

  DOI：

文献信息

• 3,3-Dimethylallyldiisopinocampheylborane: A novel reagent for chiral isoprenylation of aldehydes. Synthesis of (+)- and (−)-artemisia alcohol in exceptionally high enantiomeric purity
  作者：Herbert C. Brown、Prabhakar K. Jadhav

  DOI：10.1016/s0040-4039(01)80116-7

  日期：1984.1

  3,3-Dimethylallyldiisopinocampheylborane, on condensation with aldehydes, furnishes 3,3-dimethyl-l-alken-4-ols in 89–96% ee, including artemisia alcohol (96% ee) in both natural enantiomeric forms.

  3,3-二甲基烯丙基二硫代樟脑硼烷与醛缩合后，得到89,96％ee的3,3-二甲基-1-烯基-4-醇，包括两种天然对映体形式的蒿醇（96％ee）。
• A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua
  作者：Devin R. Polichuk、Yansheng Zhang、Darwin W. Reed、Janice F. Schmidt、Patrick S. Covello

  DOI：10.1016/j.phytochem.2010.04.026

  日期：2010.8

  The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia x inter-media secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess
  作者：Prabhakar K. Jadhav、Krishna S. Bhat、P. Thirumalai Perumal、Herbert C. Brown

  DOI：10.1021/jo00354a003

  日期：1986.2
• Chiral synthesis via organoboranes. 35. Simple procedures for the efficient recycling of the terpenyl chiral auxiliaries and convenient isolation of the homoallylic alcohols in asymmetric allyl- and crotylboration of aldehydes
  作者：Herbert C. Brown、Uday S. Racherla、Y. Liao、Vijay V. Khanna

  DOI：10.1021/jo00050a044

  日期：1992.11

  Asymmetric allyl- and crotylboration of aldehydes, RCHO, with terpenyl-based allyl- and crotylborane reagents Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3, Ter* = Ipc, 4-Icr and 2-Icr; All = allyl and Crt = crotyl), afford Ter2*BOCH*(R)C*(1R)(2R)CH=CH2 intermediates 4. In these reactions, the isolation of homoallylic alcohols, HOCH*(R)C*(1R)(2R)CH--CH2 (5), can be accomplished via oxidation of 4 with alkaline hydrogen peroxide. Unfortunately, oxidative workup destroys the chiral auxiliary and produces a large amount of nonrecyclable byproduct, terpenol (Ter*OH). Further, isolation of the pure homoallylic alcohol by distillation can be difficult if it boils in the range of the abundant byproduct. Therefore, in order to recycle the chiral auxiliaries and isolate the product homoallylic alcohols in an efficient manner, we have developed the following procedures: (1) elimination workup, in which enantiomerically pure alpha-pinene and DELTA2- and DELTA3-carenes are liberated from terpenylborinates 4 by treatment with isobutyraldehyde and 1 mol % BF3.OEt2; (2) ethanolamine workup involving treatment of 4 with ethanolamine (EA) to achieve the precipitation of the ethanolamine adducts (EA-BTer2*, Ter* = Ipc and 2-Icr, 11 and 12) from which the Ter2*BOMe can be easily regenerated; and (3) 8-hydroxyquinoline workup, involving treatment of 4 with 8-hydroxyquinoline (8-HQ) to precipitate the 8-HQ adducts (8-HQ-BTer2*, Ter* = Ipc, 4-Icr and 2-Icr, 13-15), from which the various Ter2*BOMe intermediates can be conveniently liberated. It is hoped that these procedures will significantly enhance the scope of asymmetric allyl-/crotylboration of aldehydes with Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3) and serve as excellent alternatives for any catalytic versions yet to be discovered.
• JADHAV, P. K.;BHAT, K. S.;PERUMAL, P. T.;BROWN, H. C., J. ORG. CHEM., 1986, 51, N 4, 432-439
  作者：JADHAV, P. K.、BHAT, K. S.、PERUMAL, P. T.、BROWN, H. C.

  DOI：——

  日期：——