(4R,4aS,8aR)-6-methyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-one | 94425-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,4aS,8aR)-6-methyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-one
• 英文别名: (4R,4aS,8aR)-4-isopropyl-6-methyl-3,4,4a,7,8,8a-hexahydronaphthalen-1(2H)-one；(4R,4aS,8aR)-6-methyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one
• CAS: 94425-73-7
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: KCAJPTZQBDXJMH-JHJVBQTASA-N

物化性质

• 沸点：
  295.9±19.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  (4R,4aS,8aR)-6-methyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-one 在 sodium methylate 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 44.0h， 生成 (1aR,3aS,7R,7aR,7bS)-7-Isopropyl-1a-methyl-4-methylene-decahydro-1-oxa-cyclopropa[a]naphthalene
  参考文献：
  名称：

  钾盐烷二萜全合成的进展。

  摘要：

  [请参阅结构]。描述了对从棘轮藻属物种中分离的海洋二萜类化合物，例如卡利西醇A的总合成的研究。通过分子内Diels-Alder环化，然后进行非对映选择性环氧化和叠氮化，可实现功能化反式十氢化萘核心（11）的高效构建。

  DOI：

  10.1021/ol015828k
• 作为产物：
  描述：

  (R)-Carvone 在 platinum(IV) oxide 吡啶 、 lithium aluminium tetrahydride 、 水 、 氢气 、 碘 、 铬酸 、 二异丁基氢化铝 、 magnesium 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 79.49h， 生成 (4R,4aS,8aR)-6-methyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-one
  参考文献：
  名称：

  Synthesis of both the enantiomers of sclerosporin and sclerosporal, sporogenic substance of sclerotinia fructicola

  摘要：

  DOI：

  10.1016/s0040-4020(01)91347-x

文献信息

• Relative and Absolute Structure Assignments of Alkenes Using Crystalline Osmate Derivatives for X-ray Analysis
  作者：Alexander S. Burns、Charles Dooley、Paul R. Carlson、Joseph W. Ziller、Scott D. Rychnovsky

  DOI：10.1021/acs.orglett.9b04133

  日期：2019.12.20

  stable crystalline adducts with alkenes. The structure of liquid alkenes can be determined through the X-ray analysis of these derivatives. Osmium, a heavy atom, facilitates the crystallographic analysis and the determination of the absolute configuration using common Mo X-ray sources. The utility of this method for assigning structures and absolute configurations was demonstrated on a number of unsaturated

  四氧化和TMEDA与烯烃形成稳定的结晶加合物。液态烯烃的结构可以通过对这些衍生物的X射线分析来确定。common是重原子，可使用常见的Mo X射线源促进晶体学分析和确定绝对构型。在许多不饱和底物上证明了该方法用于分配结构和绝对构型的效用，这些不饱和底物包括简单的烯烃，烯酮，烯醇醚和甲硅烷基烯醇醚。
• Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog <i>Hyperolius cinnamomeoventris</i>
  作者：Angelique Ladwig、Markus Kroll、Stefan Schulz

  DOI：10.3762/bjoc.19.16

  日期：——

  Hyperolid reed frogs are one of the few families of Anurans known to possess glands that emit volatile compounds used in chemical communication. Hyperolius cinnamomeoventris, a model species, possesses a gular gland on its vocal sac that emits chemicals, and sends visual and auditory signals during calling. Previous investigations have shown that the glandular compounds are typically macrocyclic lactones. However, in this work, we show that another major constituent of the male specific gland is (10R,1S,6R,7R,10R)-amorph-4-ene-10β-ol [(1R,4R,4aR,8aS)-4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol]. This compound was synthesized for the first time and has the opposite configuration to amorph-4-ene-10β-ol known from plants. A short synthesis using an organocatalytic approach through a tandem Mannich/intramolecular Diels–Alder reaction led to a mixture of cadinols, which was used for the assignment of the natural cadinol structures and their stereoisomers.

  苇蛙（Hyperolid reed frogs）是已知的少数几个拥有腺体的无尾目动物家族之一，这些腺体能释放出用于化学交流的挥发性化合物。模式物种 Hyperolius cinnamomeoventris 的声囊上有一个腺体，能释放化学物质，并在鸣叫时发出视觉和听觉信号。以前的研究表明，腺体化合物通常是大环内酯。然而，在这项工作中，我们发现雄性特异性腺体的另一种主要成分是（10R,1S,6R,7R,10R）-吗啉-4-烯-10β-醇[(1R,4R,4aR,8aS)-4-异丙基-1,6-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-醇]。该化合物是首次合成，其构型与植物中已知的非晶-4-烯-10β-醇相反。通过串联曼尼希/分子内 Diels-Alder 反应，使用有机催化方法进行简短合成，得到了一种卡丁醇混合物，并用于确定天然卡丁醇结构及其立体异构体。
• Antimalarial Properties of Simplified Kalihinol Analogues
  作者：Mary Elisabeth Daub、Jacques Prudhomme、Choukri Ben Mamoun、Karine G. Le Roch、Christopher D. Vanderwal

  DOI：10.1021/acsmedchemlett.7b00013

  日期：2017.3.9

  Several kalihinol natural products, members of the broader isocyanoterpene family of antimalarial agents, are potent inhibitors of Plasmodium falciparum, the agent of the most severe form of human malaria. Our previous total synthesis of kalihinol B provided a blueprint to generate many analogues within this family, some as complex as the natural product and some much simplified and easier to access. Each analogue was tested for blood-stage antimalarial activity using both drug-sensitive and -resistant P. falciparum strains. Many considerably simpler analogues of the kalihinols retained potent activity, as did a compound with a different decalin scaffold made in only three steps from sclareolide. Finally, one representative compound showed reasonable stability toward microsomal metabolism, suggesting that the isonitrile functional group that is critical for activity is not an inherent liability in these compounds.
• Synthesis of the enantiomers of sclerosporin and sclerosporal to determine the absolute configuration of the natural products
  作者：Takeshi Kitahara、Tatsuji Matsuoka、Masato Katayama、Shingo Marumo、Kenji Mori

  DOI：10.1016/s0040-4039(01)91234-1

  日期：1984.1
• Total synthesis of (±)-epicubenol
  作者：David E. Cane、Manish Tandon

  DOI：10.1016/s0040-4039(00)73497-6

  日期：1994.7

  The sesquiterpenoid microbial metabolite (+/-)-epicubenol (1) has been synthesized in 8 steps from a readily available diene aldehyde (7) using an intramolecular Diels-Alder reaction.