(E,S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one | 101979-53-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E,S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one
• 英文别名: (E,3S)-3-hydroxy-5-phenyl-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one
• CAS: 101979-53-7
• 化学式: C₁₇H₂₁NO₂S₂
• 分子量: 335.491
• InChiKey: IKCOVRIKOGAUIT-VMFRVMOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 (R)-1-(4-异丙基-2-硫氧代噻唑啉-3-基)乙酮 在 二氯苯酚溴酯 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以61%的产率得到(E,S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one
  参考文献：
  名称：

  Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione

  摘要：

  The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained preferentially when 2 equiv of Lewis acid and 1 equiv of base were employed. The anti aldol product was obtained preferentially when 1 equiv of Lewis acid and 2 equiv of base were employed for unsaturated aldehydes. Unexpected results were found with hindered aldehydes when 2 equiv of base were employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.008

文献信息

• Enantioselective Total Synthesis of Brevetoxin A: Unified Strategy for the B, E, G, and J Subunits
  作者：Michael T. Crimmins、J. Michael Ellis、Kyle A. Emmitte、Pamela A. Haile、Patrick J. McDougall、Jonathan D. Parrish、J. Lucas Zuccarello

  DOI：10.1002/chem.200900776

  日期：2009.9.14

  oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring‐closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium‐ring ethers. The strategies developed for the syntheses of these four monocycles

  Brevetoxin A 是一种十环梯形毒素，具有 5、6、7、8 和 9 元氧杂环，以及 22 个四面体立体中心。在此，我们描述了基于来自相应二烯的闭环复分解策略的 B、E、G 和 J 环的统一方法。我们实验室开发的烯醇技术允许获得 B、E 和 G 中环醚的前体无环二烯。为合成这四个单环而开发的策略最终提供了数克数量的每个环，支持我们为完成短毒素 A 的收敛合成所做的努力。
• Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain
  作者：Thomas E. Smith、Mabel Djang、Alan J. Velander、C. Wade Downey、Kathleen A. Carroll、Sophie van Alphen

  DOI：10.1021/ol0493960

  日期：2004.7.1

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.
• New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes
  作者：Yoshimitsu Nagao、Yuichi Hagiwara、Toshio Kumagai、Masahito Ochiai、Takehisa Inoue、Keiji Hashimoto、Eiichi Fujita

  DOI：10.1021/jo00362a047

  日期：1986.6
• Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A
  作者：Ángel González、Josep Aiguadé、Félix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(96)02055-2

  日期：1996.12

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd
• YOSHIMITSU NAGAO; YUICHI HAGIWARA; KUMAGAI TOSHIO; MASAHITO OCHIAI, J. ORG. CHEM., 51,(1986) N 12, 2391-2393
  作者：YOSHIMITSU NAGAO、 YUICHI HAGIWARA、 KUMAGAI TOSHIO、 MASAHITO OCHIAI

  DOI：——

  日期：——