(-)-(1R,2R,3R)-3-hydroxymethyl-1,3-dimethylbicyclo[2.2.1]heptan-2-ol | 33073-53-9

• 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: (-)-(1R,2R,3R)-3-hydroxymethyl-1,3-dimethylbicyclo[2.2.1]heptan-2-ol
• 英文别名: (-)-(1R,2R,3R)-9-hydroxyfenchol；(1R,2R,3R,4S)-3-(hydroxymethyl)-1,3-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 33073-53-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: LMQIFHGRYOSZMB-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2R,3R)-3-hydroxymethyl-1,3-dimethylbicyclo[2.2.1]heptan-2-ol 、 乙酸酐 在 吡啶 作用下， 反应 4.0h， 以4 mg的产率得到(+)-(1R,2R,3R)-3-acetoxymethyl-1,3-dimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Biotransformation of (+)-(1R,2S)-fenchol by the larvae of common cutworm (Spodoptera litura)

  摘要：

  Biotransformation of (+)-(1R,2S)-fenchol by the larvae of Spodoptera litura was carried out. Substrate was converted to three new terpenoids, (+)-(1R,2S)-10-hydroxyfenchol, (+)-(1R,2R,3S)-8-hydroxyfenchol and (-)-(1S,2S,6S)-6-exo-hydroxyfenchol, and one known terpenoid, (-)-(1R,2R,3R)-9-hydroxyfenchol. These structures were established by NMR, IR, specific rotation and mass spectral studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.076
• 作为产物：
  描述：

  Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-1,3-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 lithium aluminium tetrahydride 作用下， 生成 (-)-(1R,2R,3R)-3-hydroxymethyl-1,3-dimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Grison,C.; Bessiere-Chretien,Y., Bulletin de la Societe Chimique de France, 1972, p. 4570 - 4575

  摘要：

  DOI：

文献信息

• Studies on terpenes. Part I. Rearrangement of 7-oxatricyclo[4,3,0,0]nonanes into 8-substituted 1,3,3-trimethylnorbornane derivatives
  作者：N. Bosworth、P. D. Magnus

  DOI：10.1039/p19720000943

  日期：——

  9-Methyl-6-p-tolyl-(III; R = C6H4Me-p) and 6,9-dimethyl-7-oxatricyclo[4,3,0,0]nonane (III; R = Me) are readily rearranged into 8-substituted 1,3,3-trimethylnorbornan-2α-ols by treatment with boron trifluoride–ether. 9-Methyl-7-oxatricyclo[4,3,0,0]nonane (III; R = H) is rearranged (BF3–OEt2) to a mixture of endo-3α-acetoxymethyl-3-methylnorbornan-2α-yl acetate (VIII; R = Ac) and exo-7-acetoxymethyl

  9-甲基-6-对甲苯基- （III; R = C 6 H 4 Me- p）和6,9-二甲基-7-氧杂三环[4,3,0,0]壬烷（III; R = Me）通过用三氟化硼-醚处理，可以很容易地将它们重新排列成8-取代的1,3,3-三甲基降冰片烷-2α-醇。9-甲基-7-氧杂三环[4,3,0,0]壬烷（III; R = H）重新整理（BF 3 -OEt 2）到的混合物内-3α乙酰氧基-3- methylnorbornan-2α基乙酸（VIII； R ＝ Ac）和外-7-乙酰氧基甲基-7-甲基降冰片烷-2β-乙酸乙酸酯（IX； R ＝ Ac）。