4-(tert-butyldimethylsilyloxy)cyclohex-1-en-1-yl trifluoromethanesulfonate | 865869-24-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硅烷
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 4-(tert-butyldimethylsilyloxy)cyclohex-1-en-1-yl trifluoromethanesulfonate
• 英文别名: 4-((tert-Butyldimethylsilyl)oxy)cyclohex-1-en-1-yl trifluoromethanesulfonate；[4-[tert-butyl(dimethyl)silyl]oxycyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 865869-24-5
• 化学式: C₁₃H₂₃F₃O₄SSi
• 分子量: 360.47
• InChiKey: HOAIDAOBRMADDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilyloxy)cyclohex-1-en-1-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 氢氟酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.33h， 生成 4-vinyl-3-cyclohexenol
  参考文献：
  名称：

  Enantioselective Diels−Alder Cycloadditions with (SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone:  Efficient Kinetic Resolution of Chiral Racemic Vinylcyclohexenes

  摘要：

  Chiral racemic vinylcyclohexenes 1a-m, bearing allylic and nonallylic oxygenated substituents on the cyclohexene ring, were submitted to Diels-Alder reactions with enantiomerically pure (SS)(2-p-tolylsulfinyl)-1,4-naphthoquinone. The tandem cycloaddition/pyrolytic sulfoxide elimination led to the formation of enantiomerically enriched angularly tetracyclic quinones (+)-8a and (+)-12, arising from the kinetic resolution of the racemic diene. Dienes la-c, bearing an alkoxy substituent at the allylic position C-3, and 1d-g, with C-3 alkoxy and C-5 methyl groups, gave exclusively quinones (+)-8a-g, resulting from the anti approach to the dienophile. A similar anti selectivity occurred in cycloadditions of dienes 1ij, viith the alkoxy group situated at the allylic position C-6. Nonallylic 4-substituted vinylcyclohexenes 1k-m evolved to ca. 75:25 mixtures of (+)-anti-8k-m and (+)-syn-12k-m derivatives. In all cases, (SS)-(2-p-tolylsulfinyl)-1,4-naphthoquinone reacted from the less hindered face of the more reactive s-cis conformation, giving rise to products in moderate to excellent enantiomeric excesses. Steric effects and torsional interactions in the corresponding approaches account for the observed pi-facial diastereoselectivities at both partners.

  DOI：

  10.1021/jo9811874
• 作为产物：
  描述：

  4-羟基环己酮乙二醇缩醛 在 咪唑 、 cerium(III) chloride 、 双(三甲基硅烷基)氨基钾 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 4-(tert-butyldimethylsilyloxy)cyclohex-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Enantioselective Diels−Alder Cycloadditions with (SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone:  Efficient Kinetic Resolution of Chiral Racemic Vinylcyclohexenes

  摘要：

  Chiral racemic vinylcyclohexenes 1a-m, bearing allylic and nonallylic oxygenated substituents on the cyclohexene ring, were submitted to Diels-Alder reactions with enantiomerically pure (SS)(2-p-tolylsulfinyl)-1,4-naphthoquinone. The tandem cycloaddition/pyrolytic sulfoxide elimination led to the formation of enantiomerically enriched angularly tetracyclic quinones (+)-8a and (+)-12, arising from the kinetic resolution of the racemic diene. Dienes la-c, bearing an alkoxy substituent at the allylic position C-3, and 1d-g, with C-3 alkoxy and C-5 methyl groups, gave exclusively quinones (+)-8a-g, resulting from the anti approach to the dienophile. A similar anti selectivity occurred in cycloadditions of dienes 1ij, viith the alkoxy group situated at the allylic position C-6. Nonallylic 4-substituted vinylcyclohexenes 1k-m evolved to ca. 75:25 mixtures of (+)-anti-8k-m and (+)-syn-12k-m derivatives. In all cases, (SS)-(2-p-tolylsulfinyl)-1,4-naphthoquinone reacted from the less hindered face of the more reactive s-cis conformation, giving rise to products in moderate to excellent enantiomeric excesses. Steric effects and torsional interactions in the corresponding approaches account for the observed pi-facial diastereoselectivities at both partners.

  DOI：

  10.1021/jo9811874

文献信息

• [EN] COMPOUNDS AND METHODS FOR MODULATING FXR<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR MODULER LE FXR
  申请人：LILLY CO ELI

  公开号：WO2009012125A1

  公开（公告）日：2009-01-22

  Compounds of formula (I): formula (I) wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and diseases related to dyslipidemia.

  公式(I)的化合物：其中变量如本文所述定义，其药物组合物及其用途被披露为用于治疗血脂异常以及与血脂异常相关的疾病。
• Electrochemical Synthesis of (Aza)indolines<i>via</i>Dehydrogenative [3+2] Annulation: Application to Total Synthesis of (±)-Hinckdentine A
  作者：Zhong-Wei Hou、Hong Yan、Jin-Shuai Song、Hai-Chao Xu

  DOI：10.1002/cjoc.201800301

  日期：2018.10

  An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter‐ and intramolecular annulation reactions required noble‐metal catalysts and are mostly limited to terminal alkenes or 1,3‐dienes. The electrosynthesis employs the easily available and inexpensive

  已经开发了通过芳胺与链状烯烃的脱氢[3 + 2]环合进行官能化（氮杂）二氢吲哚的电化学合成方法。先前报道的通过类似的分子间和分子内环化反应进行的合成需要贵金属催化剂，并且大多限于末端烯烃或1,3-二烯。电合成采用容易获得且便宜的二茂铁作为分子催化剂，并与二，三，甚至四取代的烯烃相容，以构建二氢吲哚以及更具挑战性的氮杂二氢吲哚。利用新开发的电合成作为关键步骤，已从市售材料中分12个步骤（最长的线性序列）完成了海洋生物碱（±）-扁桃碱A的全合成。
• [EN] PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS<br/>[FR] COMPOSES DE PYRAZINE COMME INHIBITEURS DE PHOSPHODIESTERASE 10
  申请人：AMGEN INC

  公开号：WO2010057121A1

  公开（公告）日：2010-05-20

  Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡嗪化合物、含有它们的组合物以及制备这些化合物的方法。还提供了通过抑制PDE10治疗可治疗的疾病或病症的方法，例如肥胖、非胰岛素依赖型糖尿病、精神分裂症、双相情感障碍、强迫症等。
• Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles
  作者：Joshua S. Alford、Jillian E. Spangler、Huw M. L. Davies

  DOI：10.1021/ja405043g

  日期：2013.8.14

  A highly effective synthesis of 2,3-fused pyrroles from cyclic ketones has been achieved. The transformation includes a rhodium-catalyzed reaction of 4-alkenyl-1-sulfonyl-1,2,3-triazoles featuring an unusual 4π electrocyclization. The methodology was further extended to the synthesis of indoles using a one-pot reaction starting from 1-ethynylcyclohexenes.

  已经实现了由环酮高效合成 2,3-稠合吡咯。该转化包括 4-链烯基-1-磺酰基-1,2,3-三唑的铑催化反应，具有不寻常的 4π 电环化。该方法进一步扩展到使用从 1-乙炔基环己烯开始的一锅反应合成吲哚。
• AMINOPYRIDINE AND CARBOXYPYRIDINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20100160280A1

  公开（公告）日：2010-06-24

  Pyridine and pyrimidine compounds: or a pharmaceutically acceptable salt thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , and Y are as defined in the specification; or a pharmaceutically acceptable salt thereof, wherein ring A, m, n, y, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , X 1 , X 2 , and ring A are as defined in the specification; and or a pharmaceutically acceptable salt thereof, wherein m, n, y, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , X 1 , X 2 , and ring A are as defined in the specification; compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物： 或者是根据说明书中定义的药用可接受盐，其中m、n、R1、R2、R3、R4、R5、R6、R7、X1、X2、X3、X4、X5、X6、X7、X8和Y都有所定义； 或者是根据说明书中定义的药用可接受盐，其中环A、m、n、y、R2、R3、R4、R5、R6、R7、R8、R9、X1、X2和环A都有所定义； 或者是根据说明书中定义的药用可接受盐，其中m、n、y、R2、R3、R4、R5、R6、R7、R9、X1、X2和环A都有所定义；含有它们的组合物以及制备这类化合物的方法。还提供了通过抑制PDE10治疗可治疗的疾病或病症的方法，例如肥胖、非胰岛素依赖型糖尿病、精神分裂症、双相情感障碍、强迫症等。