(+)-cis-verbanone | 921223-41-8

• 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: (+)-cis-verbanone
• 英文别名: dihydroverbenone；Pinan-4-on；Trans-Verbanon；(1S,4S,5S)-4,6,6-Trimethylbicyclo[3.1.1]heptan-2-one
• CAS: 921223-41-8
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QKGNSWNKNMFYRE-BIIVOSGPSA-N

物化性质

• 沸点：
  213.0±0.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  (+)-cis-verbanone 在 palladium on activated charcoal 聚合甲醛 、 氢气 、 sodium ethanolate 、 potassium carbonate 作用下， 生成 cis-3-Methyl-trans-verbanon
  参考文献：
  名称：

  Bessiere-Chretien,Y.; Grison,C., Bulletin de la Societe Chimique de France, 1970, p. 3103 - 3111

  摘要：

  DOI：
• 作为产物：
  描述：

  马鞭草烯醇 在 (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one)(triphenylphosphine)(dicarbonyl)iron 、 caesium carbonate 、 异丙醇 作用下， 反应 16.0h， 以60 mg的产率得到(+)-cis-verbanone
  参考文献：
  名称：

  铁催化α，β-不饱和酮的化学选择性还原

  摘要：

  本文报道了在温和的反应条件下，铁催化的α，β-不饱和酮的化学和非对映选择性还原为相应的饱和酮。DFT计算和实验工作强调，转移氢化物的还原过程比氢化过程更容易，揭示了碱的基本作用。

  DOI：

  10.1002/chem.201800995

文献信息

• Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds Promoted by Nickel Nanoparticles
  作者：Miguel Yus、Francisco Alonso、Iñaki Osante

  DOI：10.1055/s-2006-951494

  日期：2006.11

  The system composed of nickel(II) chloride, lithium metal, a catalytic polymer-supported arene, and ethanol, has been efficiently applied to the conjugate reduction of a variety of α,β-un-saturated carbonyl compounds (ketones and carboxylic acid derivatives) under very mild reaction conditions.

  由氯化镍 (II)、锂金属、催化聚合物负载的芳烃和乙醇组成的系统已有效地应用于各种 α,β-不饱和羰基化合物（酮和羧酸衍生物）的共轭还原) 在非常温和的反应条件下。
• Bicyclic derivatives that modulate voltage-gated potassium channels and methods of use thereof
  申请人：Childers E. Wayne

  公开号：US20060004108A1

  公开（公告）日：2006-01-05

  Bicyclic amide derivatives of formula (I) or tautomers or pharmaceutically acceptable salts thereof or both are provided: Also provided are processes for preparing the bicyclic amide derivatives as well as pharmaceutical compositions containing the same and therapeutic uses. The bicyclic amide derivatives are useful for treating a variety of conditions associated with the abnormal modulation of one or more Kv1.1 voltage-gated potassium channels.

  提供式(I)的双环酰胺衍生物或其互变异构体或药用可接受的盐或两者：还提供了制备双环酰胺衍生物的方法，以及含有相同物质的药用组合物和治疗用途。这些双环酰胺衍生物可用于治疗与一个或多个Kv1.1电压门控钾通道异常调节相关的各种疾病。
• Photoisomerization of Bicyclo[3.1.1]heptan-2-ones in Methanol: Chemical Transformations of 'Verbanones'
  作者：Alex G. Fallis

  DOI：10.1139/v75-234

  日期：1975.6.1

  The products (predominantly unsaturated aldehydes) from photolysis in methanol of a series of 6,6-dimethylbicyclo[3.1.1]heptan-2-ones are reported. These results are rationalized on the basis of stereochemical interactions and the apparent preference for cleavage to occur adjacent to the less highly substituted α-carbon but more stable alkyl radical. It is concluded that the photochemical behavior of α-cyclobutyl ketones displays a closer parallel to the α-cyclopropyl ketones than previously recognized and that cleavage will occur preferentially on the side of the carbonyl group remote from the four-membered ring whenever possible. The synthetic steps involved in the preparation of the ketones from 'pinene' precursors are described.

  在甲醇中光解一系列6,6-二甲基双环[3.1.1]庚烷-2酮所产生的产品（主要是不饱和醛）已被报道。这些结果基于立体化学相互作用和对于裂解在次级α-碳旁边但更稳定的烷基自由基的明显偏好进行了解释。结论是α-环丁基酮的光化学行为与α-环丙基酮之间存在更为密切的平行关系，而且裂解会倾向于在可能的情况下首选发生在远离四元环的羰基一侧。描述了从“蒎烯”前体制备酮所涉及的合成步骤。
• Stereochemical editing logic powered by the epimerization of unactivated tertiary stereocenters
  作者：Yu-An Zhang、Vignesh Palani、Alexander E. Seim、Yong Wang、Kathleen J. Wang、Alison E. Wendlandt

  DOI：10.1126/science.add6852

  日期：2022.10.28

  The stereoselective synthesis of complex targets requires the precise orchestration of chemical transformations that simultaneously establish the connectivity and spatial orientation of desired bonds. In this work, we describe a complementary paradigm for the synthesis of chiral molecules and their isomers, which tunes the three-dimensional structure of a molecule at a late stage. Key to the success

  复杂目标的立体选择性合成需要精确协调化学转化，同时建立所需键的连通性和空间方向。在这项工作中，我们描述了手性分子及其异构体合成的互补范例，该范例在后期调整分子的三维结构。该策略成功的关键是开发一种由十钨酸聚阴离子和二硫化物助催化剂组成的温和且高度通用的光催化方法，该方法能够使先前构型固定的未活化的三级立体异构中心相互转化。
• Photostable cosmetic light screening compositions
  申请人：GIVAUDAN-ROURE (INTERNATIONAL) S.A.

  公开号：EP0754445A2

  公开（公告）日：1997-01-22

  The invention relates to photostable, cosmetic light-screening compositions for the protection of the human epidermis and the hairs against the ultraviolet rays of wavelengths between 320 and 400 nm, and between 290 and 400 nm respectively. In particular, it relates to such compositions which comprise, in a cosmetically acceptable vehicle containing at least one fatty phase, about 0,75, to about 5 %, in particular about 1 to about 4 % by weight, of a dibenzoylmethane type UV-A screening agent and at least about 0,5 % to about 2 %, in particular about 0,5 to about 1 % by weight, of a benzylidene type stabiliser of the general formula    represents a bridged cyclic compound having the camphor (1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one), norcamphor (bicyclo[2.2.1]heptan-2-one), nopinone (6,6-dimethyl-bicyclo[3.1.1]heptan-2-one), pinocamphone (4,6,6-trimethyl-bicyclo[3.1.1]heptan-3-one), verbanone (4,6,6-trimethyl-bicyclo[3.1.1]heptan-2-one, thujone (1-isopropyl-4-methyl-bicyclo[3.1.0] hexan-3-one) or the 4,7-methano-octahydro-inden-5-one structure, and wherein R1, R2, R3 independently signify hydrogen, lower alkyl, lower alkoxy, or 2 adjacent radicals represent methylenedioxy, and where, in case of the camphor derivatives, the ratio of the UV-A filter to the stabiliser is greater than ca.1,5 : 1, preferably ca. 2 to ca. 6 : 1, and where 4-methylbenzylidene camphor is excluded from the scope of formula I, and, optionally, at least one conventional UV-B filter.

  本发明涉及光稳定性化妆品遮光组合物，用于保护人体表皮和毛发免受波长分别为 320 至 400 纳米和 290 至 400 纳米的紫外线的伤害。 具体而言，它涉及这样的组合物：在含有至少一种脂肪相的化妆品可接受载体中，包含约 0.75%至约 5%，特别是约 1%至约 4%（按重量计）的二苯甲酰甲烷型紫外线-A 遮蔽剂，以及至少约 0.5%至约 2%（特别是约 0.5%至约 1%（按重量计））的亚苄基稳定剂，通式如下 代表一种桥式环状化合物，具有樟脑（1,7,7-三甲基-双环[2.2.1]庚-2-酮）、去樟脑（双环[2.2.1]庚-2-酮）、茚酮（6,6-二甲基-双环[3.1.1.1]庚-2-酮）、蒎烷酮（4,6,6-三甲基-双环[3.1.1]庚-3-酮）、马鞭酮（4,6,6-三甲基-双环[3.1.1]庚-2-酮）、��酮（1-异丙基-4-甲基-双环[3.其中 R1、R2、R3 独立表示氢、低级烷基、低级烷氧基，或 2 个相邻基表示亚甲基二氧基，如果是樟脑衍生物，则 UV-A 过滤器与稳定剂的比例大于约 1.5: 1，优选约 2 至约 6 : 1，且 4-甲基亚苄基樟脑不在式 I 的范围内，以及可选的至少一种常规 UV-B 过滤器。