(1S)-1,5,5-trimethyl-norbornane-2exo-ol | 95839-58-0

• 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: (1S)-1,5,5-trimethyl-norbornane-2exo-ol
• 英文别名: (1S)-1,5,5-Trimethyl-norbornan-2exo-ol；(-)-α-Isofenchol；(1S)-1.3.3-Trimethyl-norbornanol-(6exo)；(1S:6R)-1.3.3-Trimethyl-norbornanol-(6)；(-)-exo-Isofenchol；α-Isofenchol；(1S,2R,4S)-1,5,5-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 95839-58-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: QNNGNRWQCQDOMF-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (1S)-1,5,5-trimethyl-norbornane-2exo-ol 在 chromium(VI) oxide 、 selenium(IV) oxide 、 硫酸 、 溶剂黄146 作用下， 生成 isofenchoquinone
  参考文献：
  名称：

  Mikrobiologische Umwandlung von bicyclischen Monoterpenen durchAbsidia orchidis(VUILL.)HAGEM. 1. Teil: Reduktion von Campherchinon und Isofenchonchinon. 17. Mitteilung über Reaktionen mit Mikroorganismen [1]

  摘要：

  Abstract(—)‐Camphorquinone (1a) was transformed to a mixture consisting of 3‐endo‐hydroxy‐camphor (2a) (40%), 3‐exo‐hydroxy‐camphor (3a) (30%) and 2‐endo‐hydroxy‐epicamphor (4a) (30%) by an aqueous suspension of the mycelium of Absidia orchidis (Vuill.) Hagem. The composition of the reduction products was determined by the NMR. spectra. Incubation of the enantiomeric (+)‐camphorquinone (1b) under the same condition yielded 3‐exohydroxy‐camphor (3b) as single product. Since both substrates form their products immediately and in the same ratio the possibility of a posterior isomerization of 3a yielding the ketols 2a and 4a can be ruled out. For comparison the course of the chemical reduction of camphorquinone (1) to the ketols (Zn in acetic acid, hydrogenation with Raney‐Ni as catalyst, NaBH4) was investigated. Camphor was not transformed by Absidia orchidis. (—)‐Isofenchonequinone (6a) yielded upon incubation with an aqueous suspension of the mycelium of Absidia orchidis exclusively 2‐endo‐hydroxy‐epi‐isofenchone (7a). The enantiomer diketone 6b gave the same result, i. e. the ketol 7b as the only transformation product. Also with isofenchonequinone the chemical reduction to the ketols by Zn in acetic acid, hydrogenation with Raney‐Ni as catalyst and NaBH4 was studied.

  DOI：

  10.1002/hlca.19690520621
• 作为产物：
  描述：

  (-)-(1S,4S)-isofenchone 在 乙醇 、 sodium 、 甲苯 作用下， 生成 (1S)-1,5,5-trimethyl-norbornane-2exo-ol
  参考文献：
  名称：

  Alder; Stein, Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 247,252, 258

  摘要：

  DOI：

文献信息

• Komppa; Beckmann, Justus Liebigs Annalen der Chemie, 1934, vol. 509, p. 51,57
  作者：Komppa、Beckmann

  DOI：——

  日期：——
• Kuczynski; Kuczynski, Roczniki Chemii, 1951, vol. 25, p. 432,444
  作者：Kuczynski、Kuczynski

  DOI：——

  日期：——
• Schmidt,H. et al., Chemische Berichte, 1966, vol. 99, p. 2736 - 2744
  作者：Schmidt,H. et al.

  DOI：——

  日期：——
• Komppa; Beckmann, Justus Liebigs Annalen der Chemie, 1933, vol. 503, p. 130,134-136
  作者：Komppa、Beckmann

  DOI：——

  日期：——
• Wallach; Neumann, Justus Liebigs Annalen der Chemie, 1901, vol. 315, p. 288
  作者：Wallach、Neumann

  DOI：——

  日期：——