(S)-4-tert-butylcyclohex-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-tert-butylcyclohex-2-enone
• 英文别名: 2-Cyclohexen-1-one, 4-(1,1-dimethylethyl)-, (4S)-；(4S)-4-tert-butylcyclohex-2-en-1-one
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: JVUQEKLVFLSSTL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (S)-4-tert-butylcyclohex-2-enone 、 lithium dimethylcuprate 生成 (3S,4S)-4-tert-butyl-3-methylcyclohexan-1-one
  参考文献：
  名称：

  COUSINS, RICHARD P. C.;SIMPKINS, NIGEL S., TETRAHEDRON LETT., 30,(1989) N1, C. 7241-7244

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,4R)-3-benzenesulfonyl-4-tert-butylcyclohex-2-enol 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 15.42h， 生成 (S)-4-tert-butylcyclohex-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。
• Enantioselective Synthesis of Functionalized Nitrocyclopropanes by Organocatalytic Conjugate Addition of Bromonitroalkanes to α,β-Unsaturated Enones
  作者：Jian Lv、Jiaming Zhang、Zhu Lin、Yongmei Wang

  DOI：10.1002/chem.200801651

  日期：2009.1.12

  A general enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of a variety of bromonitroalkanes to α,β‐unsaturated enone systems is presented. The process, efficiently catalyzed by the salts of 9‐amino‐9‐deoxyepiquinine 1 d serves as a powerful approach to the preparation of synthetically and biologically important cyclopropanes with high levels of

  提出了通过将各种溴硝基烷烃有机共轭加成到α，β-不饱和烯酮体系中来官能化硝基环丙烷的一般对映选择性合成方法。该过程可通过9-氨基-9-脱氧表奎宁1 d的盐有效催化，是制备具有高对映异构和非对映异构选择性的合成和生物学上重要的环丙烷的有力方法。由于仅使用0.6当量的溴硝基甲烷作为试剂，通过使用手性1 d作为其动力学拆分的高效催化剂，对映体纯（S）-2 e（97％  ee在51％转化率下，选择性s = 120） 。
• 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。
• Lithium N-trityl-N-(R)-1-phenethylamide, a readily available and useful base for the enantioselective formation of chiral enolates from achiral ketones
  作者：Jakub Busch-Petersen、E.J Corey

  DOI：10.1016/s0040-4039(00)01185-0

  日期：2000.9

  Lithium N-trityl-N-(R)-1-phenylethylamide (6) is a readily available and useful reagent for the enantioselective (20:1) conversion of 4-t-butylcyclohexanone to the corresponding (S)-enolate. This reaction provides access to numerous useful chiral compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enantioselective Enolborination
  作者：Dale E. Ward、Wan-Li Lu

  DOI：10.1021/ja973686c

  日期：1998.2.1