(S)-4-ethylcyclohex-2-enone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-ethylcyclohex-2-enone
• 英文别名: (4S)-4-ethylcyclohex-2-en-1-one
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: RSOCZSPPRPTGTM-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (3S,6S)-(6-ethyl-3-methoxycyclohex-1-enesulfonyl)-benzene 在 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.42h， 生成 (S)-4-ethylcyclohex-2-enone
  参考文献：
  名称：

  Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹

  摘要：

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.

  DOI：

  10.1021/ja026760m

文献信息

• Chemical synthons and intermediates
  申请人：——

  公开号：US20040138485A1

  公开（公告）日：2004-07-15

  The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

  这项发明提供了新颖的六碳和七碳末端差异化的聚丙酸酯立体四聚体和立体五聚体，可用于合成天然产物。该发明还提供了一种新颖的烷基化磺化-去磺化过程，能够高效地将对映纯环氧乙烯基磺酮转化为syn和anti二烯基硫醚，只需两步操作。
• Catalytic Desymmetrizing Dehydrogenation of 4-Substituted Cyclohexanones through Enamine Oxidation
  作者：Lihui Zhu、Long Zhang、Sanzhong Luo

  DOI：10.1002/anie.201713327

  日期：2018.2.19

  A desymmetrizing dehydrogenation process catalyzed by a chiral primary amine is described herein. The reaction proceeds through the oxidation of a ketone enamine by IBX and enables the highly enantioselective desymmetrization of 4‐substituted cyclohexanones with the generation of chiral 4‐substituted cyclohexenones containing a remote γ‐stereocenter.

  本文描述了由手性伯胺催化的脱对称化脱氢过程。该反应通过IBX对酮烯胺的氧化而进行，并能使4-取代的环己酮高度对映选择性脱对称，并生成含有较远γ-立体中心的手性4-取代的环己酮。
• Synthesis of Optically Active 4-Substituted 2-Cyclohexenones
  作者：Tania I. Houjeiry、Sarah L. Poe、D. Tyler McQuade

  DOI：10.1021/ol301874x

  日期：2012.9.7

  Recently, Nicolaou and Baran independently synthesized optically active 4-substituted 2-cyclohexenones via an efficient LION-mediated intramolecular aldol condensation. Thus far, application of their cyclization approach has been limited to ketoaldehydes where the R-group is branched. It is demonstrated that the LiOH-mediated cyclization, when applied to substrates containing unbranched R-groups, results in significant erosion of optical purity. A mechanistic justification is provided, and a set of neutral, organocatalyzed conditions is identified that enables cyclization with little loss in optical purity.
• US7501535B2
  申请人：——

  公开号：US7501535B2

  公开（公告）日：2009-03-10
• US9611287B2
  申请人：——

  公开号：US9611287B2

  公开（公告）日：2017-04-04