1,7,7-trimethylspiro(bicyclo[2.2.1]heptane-3,2'-indan)-2-on | 87359-99-7

• 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: 1,7,7-trimethylspiro(bicyclo[2.2.1]heptane-3,2'-indan)-2-on
• 英文别名: (1'R,4'S)-1',7',7'-trimethylspiro[1,3-dihydroindene-2,3'-bicyclo[2.2.1]heptane]-2'-one
• CAS: 87359-99-7
• 化学式: C₁₈H₂₂O
• 分子量: 254.372
• InChiKey: QXYVTURHSFSBCE-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  1,7,7-trimethylspiro(bicyclo[2.2.1]heptane-3,2'-indan)-2-on 在 劳森试剂 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-[(1'R,4'S)-3',3'-dimethyl-2'-methylidenespiro[1,3-dihydroindene-2,7'-bicyclo[2.2.1]heptane]-1'-yl]sulfanyl-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Oxidation of sterically-crowded selones using chloramine-T: generation and skeletal rearrangement of selone Se-imides

  摘要：

  Treatment of sterically-crowded bornane-2-selones possessing substituted bornane skeletons with chloramine-T afforded several products originated from intermediary selone Se-imides, and the direct observation of the intermediates was performed by NMR monitoring at low temperature. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01155-2
• 作为产物：
  描述：

  白樟油 、 邻二氯苄 在 sodium amide 作用下， 以 甲苯 为溶剂， 以39%的产率得到1,7,7-trimethylspiro(bicyclo[2.2.1]heptane-3,2'-indan)-2-on
  参考文献：
  名称：

  阳离子络合溶剂添加剂和官能团在烯醇锂对酯的不对称烷基化反应中的影响

  摘要：

  描述了衍生自（+）-樟脑的手性醇的丙酸酯的非对映选择性烷基化。结果表明，立体屏蔽以及阳离子络合对于立体选择都很重要。后者的影响部分基于（Z）-或（E）-锂烯醇盐的优先形成而合理化。

  DOI：

  10.1016/s0040-4039(00)88138-1

文献信息

• Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis(1,5-cyclooctanediylboryl) Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Michiko Kawaguchi、Kumiko Dobashi、Yumi Nagano、Manabu Fujimura、Eiichi Kudoh、Tomonari Kai、Noboru Saito、Jun-ichi Masuda、Masaki Iwaya、Hiroyuki Fujisawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.70.197

  日期：1997.1

  Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis(1,5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2,3-dimethyl-1,3-butadiene to give the corresponding [4+2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding selenoamides, a selenoester, and sterically protected selones, respectively, in modest yields. On the other hand, a similar treatment of cinnamaldehyde with the reagent gave the 2,3-dihydroselenophene derivative, which originated from a [4+2]-type self-dimerization of in situ generated 3-phenyl-2-propeneselenal.

  在原位生成硒醛和硒酮，通过将醛或酮与双(1,5-环辛烷二基)硒化物处理；由此得到的硒羰基化合物与2,3-二甲基-1,3-丁二烯反应，形成相应的[4+2]环加成物。将具有体积较大取代基的酰胺、酯和酮与该试剂处理，亦分别得到相应的硒酰胺、硒酯和体积保护的硒酮，产率适中。另一方面，将肉桂醛与该试剂处理，得到2,3-二氢硒苯衍生物，这源于原位生成的3-苯基-2-丙烯硒醛的[4+2]型自聚合反应。
• Preparation of Optically Active 1-Aminoalkylphosphonic Acids from Chiral Carbamates and Chiral Ureas
  作者：Tatsuo Oshikawa、Mitsuji Yamashita

  DOI：10.1246/bcsj.62.3177

  日期：1989.10

  Optically active 1-aminoalkylphosphonic acids were successfully synthesized from chiral carbamate and urea derivatives which were prepared from such chiral substrates as (−)-menthol, (+)-camphor, and (R)-(+)-and (S)-(−)-(1-phenylethyl)ureas by the actions of aldehydes and triaryl phosphites. 1-Aminoalkylphosphonic acid derivatives, thus prepared, have an (R)-(+)- or (S)-(−)-configuration, depending

  以(-)-薄荷醇、(+)-樟脑、(R)-(+)-和(S)-等手性底物制备的手性氨基甲酸酯和尿素衍生物成功合成了具有旋光活性的1-氨基烷基膦酸。 -)-(1-苯乙基)脲通过醛和亚磷酸三芳基酯的作用。如此制备的1-氨基烷基膦酸衍生物具有(R)-(+)-或(S)-(-)-构型，这取决于通过构型保留的手性来源；即，(+)-产物由手性(+)-氨基甲酸酯和(+)-脲衍生物制备，(-)-产物由手性(-)-氨基甲酸酯和(-)-脲衍生物制备。
• Formation of Kinetically Stabilized Dithiiranes by Treating Thione<i>S</i>-Oxides Bearing a Bulky Substituent with Lawesson’s Reagent
  作者：Kazuaki Shimada、Keiichi Kodaki、Shigenobu Aoyagi、Yuji Takikawa、Chizuko Kabuto

  DOI：10.1246/cl.1999.695

  日期：1999.7

  Treatment of sterically crowded thione S-oxides derived from d-camphor with Lawesson’s reagent afforded dithiiranes along with deoxygenation of the starting materials, and the mixtures were subjected to mCPBA oxidation to give the corresponding dithiirane S-oxides and thione S-oxides.

  用 Lawesson 试剂处理源自 d-樟脑的空间拥挤的硫酮 S-氧化物，得到二硫杂环丙烷，同时对起始材料进行脱氧，并将混合物进行 mCPBA 氧化，得到相应的二硫杂环硫醚 S-氧化物和硫酮 S-氧化物。
• ¹ H NMR-based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative
  作者：Kevin A. Lobb、Perry T. Kaye

  DOI：10.1002/poc.1699

  日期：2011.1

  1H NMR analysis of the kinetics of skeletal rearrangement of optically pure 3,3‐xylyl‐2‐exo‐bornyl tosylate in CDCl3 indicates the operation of tandem autocatalytic and pseudo‐first‐order transformations, leading sequentially to a pair of isomeric camphene derivatives and involving partial racemization. Changing the solvent system has been shown to permit the chemoselective isolation of either of the

  1个光学纯的3,3-二甲苯基-2-骨架重排的动力学的H NMR分析外切在CDCl -bornyl甲苯磺酸盐3表示串联自催化和伪一阶变换的操作中，顺序地导致一对异构体莰烯的派生和涉及部分消旋。已经表明，改变溶剂系统可以实现对任何异构体樟脑的化学选择性分离。版权所有©2010 John Wiley＆Sons，Ltd.
• Diastereoselectivity in α-Benzylation Reactions of Esters of Spiro[bornane-3,2′-indan]-2-<i>exo</i>-ol
  作者：Melanie D. Evans、Perry T. Kaye

  DOI：10.1080/00397919808004484

  日期：1998.12

  The alpha-benzylation of a series of alkanoic esters of spiro[bornane-3,2'-indan]-2-exo-ol has been investigated and shown to proceed in 9-60 % d.e.