N-<(R)-3-hydroxy-4E-hexenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane | 167259-97-4

• 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-<(R)-3-hydroxy-4E-hexenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• 英文别名: N-<(R)-(E)-3-Hydroxy-4-hexenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane；N-<(R)-3-Hydroxy-4-hexenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane；(E,3R)-1-[(1S,5R,7R)-10,10-dimethyl-3-sulfanylidene-4-oxa-2-azatricyclo[5.2.1.01,5]decan-2-yl]-3-hydroxyhex-4-en-1-one
• CAS: 167259-97-4
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: KRVLMZIJINFWIT-MLMZUUSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(R)-3-hydroxy-4E-hexenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4E)-3-hydroxy-4-hexenoic acid
  参考文献：
  名称：

  An Unusual Enantioselective Aldol-Type Reaction of an Acetate Boryl Enolate Derived from a Chiral Thioimide

  摘要：

  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.

  DOI：

  10.1021/jo00105a040
• 作为产物：
  描述：

  (1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 sodium hydride 、 N,N-二异丙基乙胺 、 9-硼杂双环[3.3.1]壬基三氟甲磺酸酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 N-<(R)-3-hydroxy-4E-hexenoyl>-(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：

  An Unusual Enantioselective Aldol-Type Reaction of an Acetate Boryl Enolate Derived from a Chiral Thioimide

  摘要：

  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.

  DOI：

  10.1021/jo00105a040

文献信息

• Yan, Tu-Hsin; Hung, An-Wei; Lee, Hui-Chun, Journal of the Chinese Chemical Society, 1995, vol. 42, # 4, p. 691 - 700
  作者：Yan, Tu-Hsin、Hung, An-Wei、Lee, Hui-Chun、Liu, Wen-Hung、Chang, Chii-Shin

  DOI：——

  日期：——
• 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.
• 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.