(S)-3-(1'-methylethyl)cycloheptanone

• 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: (S)-3-(1'-methylethyl)cycloheptanone
• 英文别名: 3-(S)-(2'-methylethyl)-cycloheptanone；3-isopropylcycloheptanone；(3S)-3-propan-2-ylcycloheptan-1-one
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: FADJMQQFGSBLND-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  2-环庚烯-1-酮 、 二异丙基锌 在 copper(I) trifluoromethanesulfonate benzene 、 [(2-PPh₂)C₆H₄CH]-t-Leu-t-Bu-Tyr-Gly-OMe 作用下， 以 甲苯 为溶剂， 生成 (R)-3-(1'-methylethyl)cycloheptanone 、 (S)-3-(1'-methylethyl)cycloheptanone
  参考文献：
  名称：

  不对称催化中基于模块肽的膦配体：对五元，六元和七元环状烯酮的高效和对映选择性的铜催化共轭加成。

  摘要：

  DOI：

  10.1021/ja003698p

文献信息

• Preparation and Characterization of New C2- and C1-Symmetric Nitrogen, Oxygen, Phosphorous, and Sulfur Derivatives and Analogs of TADDOL. Part I
  作者：Arkadius Pichota、Volker Gramlich、Albert K. Beck、Dieter Seebach

  DOI：10.1002/hlca.201200146

  日期：2012.8

  from TADDOLs (=α,α,α′,α′‐tetraaryl‐1,3‐dioxolan‐4,5‐dimethanols) are used to prepare corresponding sulfanyl alcohols, ethers, and amines (Scheme 1 and Table 1). The dithiol analog of TADDOL and derivatives thereof, 45–49, were also synthesized. The crystal structures of 16 representatives of this series of compounds are reported (Figs. 1–3 and Scheme 2). The thiols were employed in Cu‐catalyzed enantioselective

  所述氯醇4 - 6从TADDOLs衍生（= α，α，α' ，α' -tetraaryl -1,3-二氧戊环-4,5-二甲醇）来制备相应的硫烷基醇，醚，和胺（方案1和表1）。TADDOL以及它们的衍生物，二硫醇的模拟45 - 49，还合成。据报道该系列化合物的16所代表的晶体结构（图1。 - 3和方案2）。硫醇用于格利雅铜的铜催化对映选择性共轭添加环庚酮的最佳试剂（最高可达94：6）。从对映选择性反转的Si -addition与硫烷基醇重新-addition与烷氧基或二甲氨基硫醇（表4）。铜我-Thiolates，50 - 53，有可能在高达84％的收率（分离方案2），并显示出具有在气相中四核结构（通过ESI-MS），在溶液（CH 2氯2，THF;通过蒸汽渗透压法和NMR脉冲梯度扩散测量;表5），以及处于固态（方案2中的X射线晶体结构））。硫烷醇的Cu络合物50在空气中和弱酸水溶液中均稳定，并且是1
• Chiral mercaptoaryl-oxazolines as ligands in enantioselective copper-catalyzed 1,4-additions of Grignard reagents to enones
  作者：Zhou Qi-Lin、Andreas Pfaltz

  DOI：10.1016/s0040-4020(01)89379-0

  日期：1994.4

  A series of chiral enantiomerically pure mercaptoaryl-oxazolines has been synthesized. Copper(I) thiolate complexes derived from these ligands proved to be efficient catalysts for the 1,4-addition of Grignard reagents to cyclic enones. Enantioselectivities increased in the sequence cyclopentenone (16–37% ee) < cyclohexenone (60–72% ee) < cycloheptenone (83–87% ee).

  已经合成了一系列手性对映体纯的巯基芳基-恶唑啉。衍生自这些配体的硫醇铜（I）络合物被证明是格氏试剂向环状烯酮1,4-加成的有效催化剂。对映选择性按顺序依次增加：环戊烯酮（16-37％ee）<环己烯酮（60-72％ee）<环庚烯酮（83-87％ee）。
• Enantioselective 1,4-Addition of AliphaticGrignard Reagents to Enones Catalyzed by Readily Available Copper(I) thiolates derived from TADDOL. Preliminary communication
  作者：Dieter Seebach、Georg Jaeschke、Arkadius Pichota、Laurent Audergon

  DOI：10.1002/hlca.19970800819

  日期：1997.12.15

  thiols derived from the parent TADDOL, α,α,α′,α′ tetraphenyl-2,2-dimethyl-1,3-clioxolan-4,5-dimethanol, are used to prepare Cu1 complexes C and D to catalyze (0.05 equiv.) 1,4-additions of Grignard reagents RMgCl to cyclic enones with enantioselectivities which are comparable to or better than previously reported (enantiomer ratios up to 92:8).

  衍生自母体TADDOL的两种简单的硫醇α，α，α'，α'四苯基-2,2-二甲基-1,3-clioxolan-4,5-二甲醇用于制备Cu 1配合物C和D进行催化（0.05当量）格氏试剂RMgCl向环状烯酮中添加1,4- ，其对映体选择性与先前报道的对映体相当或更好（对映体比例高达92：8）。
• Highly Practical and Enantioselective Cu-Catalyzed Conjugate Addition of Alkylzinc Reagents to Cyclic Enones at Ambient Temperature
  作者：Isaac J. Krauss、James L. Leighton

  DOI：10.1021/ol034983r

  日期：2003.9.1

  [GRAPHICS]A new ligand for Cu-catalyzed enantioselective additions of dialkylzincs to cyclic enones has been developed. In addition to providing good to excellent enantioselectivities with a range of cyclic enones and dialkylzincs, the ligand has several notworthy features: it can be readily prepared in just two steps, is an air-stable crystalline solid, and provides optimal performance at ambient temperature.