N-<(R)-(E)-3-Hydroxy-4-heptenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane | 167259-96-3

• 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)-(E)-3-Hydroxy-4-heptenoyl>-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane
• 英文别名: (E,3R)-1-[(1S,5R,7R)-10,10-dimethyl-3-sulfanylidene-4-oxa-2-azatricyclo[5.2.1.01,5]decan-2-yl]-3-hydroxyhept-4-en-1-one
• CAS: 167259-96-3
• 化学式: C₁₇H₂₅NO₃S
• 分子量: 323.456
• InChiKey: OVSQDIUQKZPYRT-HHNUNDILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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)-(E)-3-Hydroxy-4-heptenoyl>-(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 (R)-(E)-3-Hydroxy-4-heptenoic 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)-(E)-3-Hydroxy-4-heptenoyl>-(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

• 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.