缬草酮 | 5090-54-0

• 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
• 中文名称: 缬草酮
• 英文名称: valeranone
• 英文别名: Valeranon；jatamansone；Jatamanson；(-)-Valeranone；(4aS,7R,8aR)-4a,8a-dimethyl-7-propan-2-yl-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one
• CAS: 5090-54-0
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: HDVXJTYHXDVWQO-SNPRPXQTSA-N

物化性质

• LogP：
  4.640

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  缬草酮 在 sodium ethanolate 、 铜 作用下， 生成 Norvaleranon
  参考文献：
  名称：

  Krepinsky,J. et al., Collection of Czechoslovak Chemical Communications, 1962, vol. 27, p. 2638 - 2653

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,3aR,6R,7aS)-2-Iodo-6-isopropyl-1,3a,7a-trimethyl-octahydro-indene 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~160.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 缬草酮
  参考文献：
  名称：

  Srikrishna; Viswajanani; Dinesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1265 - 1274

  摘要：

  DOI：

文献信息

• Structure and stereochemistry of jatamansone
  作者：T.R. Govindachari、B.R. Pai、K.K. Purushothaman、S. Rajadurai

  DOI：10.1016/0040-4020(61)80103-8

  日期：1961.1

  On the basis of degradation studies, jatamansone is shown to have the structure and stereochemistry depicted in formula I, representing a new fundamental type.

  在降解研究的基础上，贾塔曼松被证明具有式I所示的结构和立体化学，代表一种新的基本类型。
• Structure and Absolute Configuration of Valeranone
  作者：Hiroshi Hikino、Yasuko Hikino、Yasuyoshi Takeshita、Kanji Meguro、Tsunematsu Takemoto

  DOI：10.1248/cpb.13.1408

  日期：——

  The structure and absolute configuration of valeranone have been established as V from the following evidence. Valeranone (V) was converted into IX via VIII (R=O, X=H), and β-eudesmol (X ; R=CH2) into XVI via XV (X=H). VIII (R=O, X=H) was shown to be a diastereomer of XV (X=H), and IX the enantiomer of XVI, thus establishing the absolute configuration of the C-10 methyl as α and that of the C-7 isopropyl group as β. The absolute configuration of the C-5 methyl was confirmed to be α by observing a negative Cotton effect of XXI, the difference of the nuclear magnetic resonance signals of the C-5 methyl of V and XXIV, and the conversion of XXII into XXIII. The absolute stereochemistry was also supported by the nuclear magnetic resonance spectra of XXVI (R=H and Ac) which revealed that the C-4 hydroxyl of R-configuration was located in a 1, 3-diaxial relation to the C-10 methyl group.

  根据以下证据将戊酮的结构和绝对构型确定为V。戊酮(V)经由VIII(R＝O，X＝H)转化为IX，且β-桉醇(X；R＝CH 2 )经由XV(X＝H)转化为XVI。 VIII (R=O，X=H)显示为XV (X=H)的非对映异构体，IX为XVI的对映异构体，从而建立了C-10甲基的绝对构型为α，C-10甲基的绝对构型为α 7个异丙基为β。通过观察XXI的负Cotton效应、V和XXIV的C-5甲基的核磁共振信号的差异以及XXII向XXIII的转化，确认C-5甲基的绝对构型为α。绝对立体化学也得到XXVI的核磁共振谱(R=H和Ac)的支持，其揭示R-构型的C-4羟基与C-10甲基处于1, 3-二轴关系。
• Terpenoids—XLVIII
  作者：K.S. Kulkarni、S.K. Paknikar、S.C. Bhattacharyya

  DOI：10.1016/s0040-4020(01)98993-8

  日期：1964.1

  and its acetyl derivative, have been isolated from Indian valerian root oil (Valeriana wallichi). On the basis of NMR spectral results along with other spectroscopic, analytical and chemical data, structure I has been assigned to hydroxyvaleranone. ORD data and chemical evidences also indicate that it is represented by the stereoformula XXIII.

  从印度缬草根油（Valeriana wallichi）中分离出了两种新的倍半萜烯，羟基缬草酮及其乙酰基衍生物。根据NMR光谱结果以及其他光谱，分析和化学数据，已将结构I分配给了羟基缬草酮。ORD数据和化学证据也表明它由立体式XXIII表示。
• Structure and Absolute Configuration of Fauronyl Acetate and Cryptofauronol
  作者：Hiroshi Hikino、Yasuyoshi Takeshita、Yasuko Hikino、Tsunematsu Takemoto

  DOI：10.1248/cpb.14.735

  日期：——

  The structure and absolute stereochemistry of fauronyl acetate and cryptofauronol have been elucidated as formulae I and II, respectively, by the following series of reactions coupled with spectral determinations. Fauronyl acetate (I) and cryptofauronol (II) were interconverted by hydrolysis and acetylation. Fauronyl acetate was transformed to the ketone (VIII), in which the environment of the carbonyl group was established, and to valeranone whose absolute stereostructure (XIV) is known.

  通过以下一系列反应并结合光谱测定，乙酸苯甲醛酯和隐苯甲醛醇的结构和绝对立体化学已分别阐明为式I和II。 Fauronyl Acetate (I) 和 Cryptofauronol (II) 通过水解和乙酰化相互转化。乙酸呋喃酯转化为酮 (VIII)，其中建立了羰基环境，并转化为绝对立体结构 (XIV) 已知的戊酮。
• Oxycyclopropanes in organochemical synthesis. Total syntheses of (-)-valeranone and (.+-.)-grandisol
  作者：Ernest Wenkert、David A. Berges、Norman F. Golob

  DOI：10.1021/ja00472a038

  日期：1978.2