N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane | 167259-92-9

• 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: N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• 英文别名: 1-[(1S,5R,7R)-10,10-dimethyl-3-sulfanylidene-4-oxa-2-azatricyclo[5.2.1.01,5]decan-2-yl]ethanone
• CAS: 167259-92-9
• 化学式: C₁₂H₁₇NO₂S
• 分子量: 239.338
• InChiKey: JBLMUDWEAIMTCF-KBVBSXBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 溴 、 四氯化钛 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.88h， 生成 (1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
  参考文献：
  名称：

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯的不对称溴化-醛醇缩合。合成对映纯α-溴-β-羟基羧酸的一般方法

  摘要：

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯可有效完成一步溴化-醛缩醛化反应，并具有优异的收率，并且在添加醛醇缩合剂时异常高的不对称诱导率。一般的碱促进的恶唑烷硫酮脱酰作用可直接获得手性α-溴-β-羟基酸。

  DOI：

  10.1016/s0040-4039(99)00576-6
• 作为产物：
  描述：

  乙酰氯 、 (1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 sodium hydride 作用下， 生成 N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
  参考文献：
  名称：

  Yan, Tu-Hsin; Hung, An-Wei; Lee, Hui-Chun, Journal of the Chinese Chemical Society, 1995, vol. 42, # 4, p. 691 - 700

  摘要：

  DOI：

文献信息

• An Unusual Enantioselective Aldol-Type Reaction of an Acetate Boryl Enolate Derived from a Chiral Thioimide
  作者：Tu-Hsin Yan、An-Wei Hung、Hui-Chun Lee、Chii-Shin Chang

  DOI：10.1021/jo00105a040

  日期：1994.12

  The camphor-derived N-acetyloxazolidinethione has been used to effect enantioselective aldol type reactions of the derived 9-BBN enolate with a variety of aldehydes. Mechanistically, the observed facial selectivity is best explained by a boatlike transition structure.
• A New Approach for the Chemoselective Debromination of Chiral Bromohydrins. Toward the Development of a Very General Approach to Enantiopure α-Unsubstituted β-Hydroxy Acids
  作者：Ying-Chuan Wang、Tu-Hsin Yan

  DOI：10.1021/jo000124u

  日期：2000.10.1
• Toward the Development of a General Chiral α-Substituted Acetate Enolate Synthon for Aldolization. DMAP- and NEt₃-Promoted Oxazolidinethione “Deacylation”
  作者：Ying-Chuan Wang、Dah-Wei Su、Chen-Men Lin、Hsi-Liang Tseng、Chi-Lung Li、Tu-Hsin Yan

  DOI：10.1021/jo990444h

  日期：1999.8.1
• An efficient method for the synthesis of enantiopure cis-α,β-epoxy acids
  作者：Ying-Chuan Wang、Chi-Lung Li、Hsi-Liang Tseng、Shang-Chi Chuang、Tu-Hsin Yan

  DOI：10.1016/s0957-4166(99)00320-1

  日期：1999.8

  Enantiopure cis-alpha,beta-epoxy acids were prepared via a modified Darzen's reaction employing the titanium-mediated bromination-aldolization of chiral acetate thioimide enolate. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Asymmetric Aldol Type Reactions of Acetate Imide Enolates
  作者：Tu-Hsin Yan、An-Wei Hung、Hui-Chun Lee、Chii-Shin Chang、Wen-Hung Liu

  DOI：10.1021/jo00116a011

  日期：1995.6

  Titanium-mediated chelation-controlled aldol type reactions of acetate thioimide enolates with representative aldehydes proceed with high ct-facial differentiation. An investigation of the influence of the nature of the imide enolate ligands and the Lewis acids in the non-chelation-controlled aldol bond construction process of acetate imide enolates reveals that alternation of either the boryl geometry or imide enolate ligand leads to pi-facial selectivity switch.