(-)-(1S,4S)-isofenchone | 17957-95-8

• 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,4S)-isofenchone
• 英文别名: isofenchone；(1S)-1,5,5-trimethyl-norbornan-2-one；(1S)-1,5,5-Trimethyl-norbornan-2-on；(-)-Isofenchon；(1S,4S)-1,5,5-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 17957-95-8
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BGKHEYBJLXKPGX-XCBNKYQSSA-N

物化性质

• 沸点：
  202.7±8.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (-)-(1S,4S)-isofenchone 在 selenium(IV) oxide 、 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：

  (4-carboxy-2,2,4-trimethyl-cyclopentyl)-acetic acid 在 barium dihydroxide 作用下， 生成 (-)-(1S,4S)-isofenchone
  参考文献：
  名称：

  46.萜烯化合物。第六部分 （±）-异雄酮的合成

  摘要：

  DOI：

  10.1039/jr9490000197

文献信息

• Influence of norbornanone substituents on both the Wagner–Meerwein skeletal rearrangements under sulfonation conditions and the diastereoselectivity of the corresponding N,N′-bis-fumaroyl sultams in uncatalyzed Diels–Alder cycloadditions to cyclopenta-1,3-diene
  作者：Anna Piątek、Christian Chapuis

  DOI：10.1016/j.tetlet.2013.05.147

  日期：2013.8

  is strongly influenced by the absence of a gem-dimethyl moiety at C(7). As a result, sulfonation at C(10) is less efficient due to a divergent pathway in the intermediate double bond formation and/or isomerization. Furthermore, the absence of such a gem-dimethyl moiety in the corresponding norbornane[10,2]sultam derivatives, sterically influences the orientation of the SO(1) and SO(2) substituents

  在磺化条件下，降冰片烷酮骨架的Wagner-Meerwein多米诺骨牌重排受到C（7）处不存在宝石-二甲基部分的强烈影响。结果，由于在中间双键形成和/或异构化中的发散途径，C（10）处的磺化效率较低。此外，在相应的降冰片烷[10,2] sultam衍生物中不存在这种宝石-二甲基部分会在空间上影响S O（1）和S O（2）取代基的取向，因此对π面空间屏蔽有影响热力学更稳定的抗-S-顺ñ-链烯酰基二亲糖。结果，在非螯合条件下，它们的非对映选择性[4 + 2]环加成到环戊-1,3-二烯上的效率不高，这是由于伪轴向S O（1）较少，并因此失去了伪C 2-对称性。 。
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1936, vol. 525, p. 247,252, 258
  作者：Alder、Stein

  DOI：——

  日期：——
• Polonski, Tadeusz; Dauter, Zbigniew, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1781 - 1788
  作者：Polonski, Tadeusz、Dauter, Zbigniew

  DOI：——

  日期：——
• ——
  作者：E. A. Dikusar、N. G. Kozlov、K. L. Moiseichuk、V. I. Potkin

  DOI：10.1023/a:1020928905078

  日期：——

  Synthesis of tertiary acetylene alcohols was developed based on 1-octadecyne treatment with butyllithium followed by reaction of 1-octadecynyllithium with aliphatic, aromatic, alicyclic, and terpene ketones.
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1935, vol. 515, p. 185
  作者：Alder、Stein

  DOI：——

  日期：——

表征谱图