(R)-2-isopropyl-5-oxohexanal | 863880-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-isopropyl-5-oxohexanal
• 英文别名: (2R)-5-oxo-2-propan-2-ylhexanal
• CAS: 863880-06-2
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: JUZXYQBZHRMZNQ-VIFPVBQESA-N

物化性质

• 沸点：
  236.0±23.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-isopropyl-5-oxohexanal 在 叔丁基锂 、 lithium isopropoxide 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 、 正戊烷 为溶剂， 反应 3.83h， 生成
  参考文献：
  名称：

  Antimalarial Properties of Simplified Kalihinol Analogues

  摘要：

  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.

  DOI：

  10.1021/acsmedchemlett.7b00013
• 作为产物：
  描述：

  (5E,9S,10E)-9-isopropyl-6,12-dimethyl-trideca-5,10,12-trien-2-one 在 臭氧 作用下， 生成 (R)-2-isopropyl-5-oxohexanal
  参考文献：
  名称：

  Aasen,A.J. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1976, vol. 30, p. 178 - 179

  摘要：

  DOI：

文献信息

• Synthesis of (−)-Piperitylmagnolol Featuring <i>ortho</i>-Selective Deiodination and Pd-Catalyzed Allylation
  作者：Atsushi Ikoma、Narihito Ogawa、Daiki Kondo、Hiroki Kawada、Yuichi Kobayashi

  DOI：10.1021/acs.orglett.6b00706

  日期：2016.5.6

  A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (−)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed

  研究了使用烯酮和铜试剂的1，4-加成策略，用于合成（-）-哌啶基厚朴酚。将MOM保护的双酚铜试剂添加到BF 3 ·OEt 2活化的4-异丙基环己烯酮中，而发现未成功添加1,4-具有烯丙基的保护单酚试剂。烯丙基随后通过Pd催化的与烯丙基硼酸酯的偶合而连接至p-，p′-二碘代-双酚环。上述碘化物使用新的方法，用于合成邻的脱碘-选择性ø - ，p -diiodophenols。
• Enantioselective Biomimetic Total Syntheses of Katsumadain and Katsumadain C
  作者：Pengtao Zhang、Yongguang Wang、Ruiyang Bao、Tuoping Luo、Zhen Yang、Yefeng Tang

  DOI：10.1021/ol2029433

  日期：2012.1.6

  Enantioselective total syntheses of katsumadain and katsumadain C were achieved concisely through a biomimetic approach. Assembly of styryl-2-pyranone (3) and monoterpene 6 via acid-promoted regio- and stereoselective C–C bond formation afforded katsumadain (2), which underwent the photoinduced [2 + 2] dimerization in a head-to-tail mode to furnish katsumadain C (1).

  通过仿生方法简明地实现了胜肽和胜肽C的对映选择性合成。通过酸促进的区域和立体选择性C–C键形成的苯乙烯-2-吡喃酮（3）和单萜6的组装提供了胜马丹（2），其以从头到尾的方式经历了光诱导的[2 + 2]二聚化。提供katsumadain C（1）。
• 一种(E)型茄酮、其制备方法及用途
  申请人：云南中烟工业有限责任公司

  公开号：CN111039770B

  公开（公告）日：2022-03-25

  本发明公开了一种(E)型茄酮，其立体结构式为：或其名称为：(S,E)‑5‑异丙基‑8‑甲基‑6,8‑二烯‑2‑酮、或(R,E)‑5‑异丙基‑8‑甲基‑6,8‑二烯‑2‑酮。本发明还公开了所述(E)型茄酮的制备方法及用于卷烟烟丝加香的用途。
• Direct Enantioselective Michael Addition of Aldehydes to Vinyl Ketones Catalyzed by Chiral Amines
  作者：Paolo Melchiorre、Karl Anker Jørgensen

  DOI：10.1021/jo026837p

  日期：2003.5.1

  enantioselectivities, using aldehydes and, e.g., methyl vinyl ketone as starting compounds. Taking into account that the chiral amine can activate the aldehyde and/or the enone, the mechanism for the reaction has been investigated. On the basis of intermediate synthesis, nonlinear effect, and theoretical investigations, the mechanism for the catalytic direct enantioselective Michael addition of aldehydes to vinyl ketones

  （S）-2- [双（3,5-二甲基苯基）甲基]吡咯烷和C（2）-对称（2S，5S）-2,5-二苯基吡咯烷等手性胺可以催化简单的对映选择性迈克尔加成反应醛到乙烯基酮。已经优化了该有机催化反应的条件，并且发现手性胺使用醛和例如甲基乙烯基酮作为起始化合物以良好的产率和对映选择性催化形成光学活性取代的5-酮醛。考虑到手性胺可以活化醛和/或烯酮，已经研究了反应机理。在中间综合，非线性效应和理论研究的基础上，
• 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。