(1S)-10-(phenylselanyl)camphor

• 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)-10-(phenylselanyl)camphor
• 英文别名: (1S,4R)-7,7-dimethyl-1-(phenylselanylmethyl)bicyclo[2.2.1]heptan-2-one
• 化学式: C₁₆H₂₀OSe
• 分子量: 307.294
• InChiKey: JSONHYSCLGJUCK-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯基氯化硒 、 (1R)-3,3-dimethyl-2-methylenenorbornan-1-ol 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到(1S)-10-(phenylselanyl)camphor
  参考文献：
  名称：

  制备对映体纯的C10-S-和C10-Se取代的樟脑衍生的硫化物和硒的简便新方法

  摘要：

  描述了从容易获得的樟脑中两种新颖的C10-S（II）-和C10-Se（II）-取代的樟脑衍生物（芳基硫醚和芳基硒化物）的对映体制备。建立的三步路线构成了直接制备有趣的对映纯C10-S-和C10-Se取代的樟脑衍生的手性来源的模型程序。所描述路线的关键步骤是在用芳基亚硫基（或芳基硒基）氯化物进行亲电处理后，对映体特异性Wagner-Meerwein重排3,3-二甲基-2-亚甲基降冰片烷-1-醇6。

  DOI：

  10.1016/s0040-4039(01)00924-8

文献信息

• Oxidation of Olefins with Benzeneseleninic Anhydride in the Presence of TMSOTf
  作者：Izabella Jastrzębska、Maja Morawiak、Joanna E. Rode、Barbara Seroka、Leszek Siergiejczyk、Jacek W. Morzycki

  DOI：10.1021/acs.joc.5b00410

  日期：2015.6.19

  been shown that different products are formed with this species depending on the specific structure of olefin. The 1,1-disubstituted olefins afforded mostly α,β-unsaturated carbonyl compounds. The sterically encumbered tri- or tetrasubstituted olefins yielded 1,2- or 1,4-dihydroxylated products, presumably via four-membered cyclic intermediates.

  研究了一种新的烯烃氧化体系，该体系由苯硒酸酐和三甲基甲硅烷基三氟甲磺酸酯组成。推测在这些条件下形成了高反应性的苯硒烯基阳离子。已经表明，取决于烯烃的具体结构，与该物质形成不同的产物。1，1-二取代的烯烃主要提供α，β-不饱和羰基化合物。在空间上受阻的三或四取代的烯烃产生了1,2-或1,4-二羟基化的产物，大概是通过四元环状中间体。
• A new convenient procedure for the preparation of enantiopure C10-S- and C10-Se-substituted camphor-derived sulfides and selenides
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Amelia Garcı́a Fraile、Santiago de la Moya Cerero、Beatriz Lora Maroto

  DOI：10.1016/s0040-4039(01)00924-8

  日期：2001.7

  The enantiospecific preparation of two novel C10-S(II)- and C10-Se(II)-substituted camphor derivatives (arylsulfide and arylselenide) from readily available camphor is described. The established three-step route constitutes a model procedure for the straightforward preparation of interesting enantiopure C10-S- and C10-Se-substituted camphor-derived chiral sources. The key-step of the described route

  描述了从容易获得的樟脑中两种新颖的C10-S（II）-和C10-Se（II）-取代的樟脑衍生物（芳基硫醚和芳基硒化物）的对映体制备。建立的三步路线构成了直接制备有趣的对映纯C10-S-和C10-Se取代的樟脑衍生的手性来源的模型程序。所描述路线的关键步骤是在用芳基亚硫基（或芳基硒基）氯化物进行亲电处理后，对映体特异性Wagner-Meerwein重排3,3-二甲基-2-亚甲基降冰片烷-1-醇6。
• C(10)-Substituted Camphors and Fenchones by Electrophilic Treatment of 2-Methylenenorbornan-1-ols:  Enantiospecificity, Scope, and Limitations
  作者：Santiago de la Moya Cerero、Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Beatriz Lora Maroto

  DOI：10.1021/jo026566i

  日期：2003.2.1

  Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchone-derived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein rearrangement. A complete study of the enantiospecificity, scope, and limitations of this process, as well as about the role played by the hydroxyl group attached at the C(1) bridgehead position of the starting 2-methylenenorbornan-1-ols, has been realized. The feasibility of the described methodology has been exemplified by the highly efficient enantiospecific preparation of several interesting C(10)-halogen-, (C10)-O-, C(10)-S-, C(10)-Se-, or C(10)-C-substituted camphors and fenchones.