(2S,3R,4R)-(-)-1-(Benzyloxy)-2,4-dimethyl-5-tridecyn-3-ol | 157379-07-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,4R)-(-)-1-(Benzyloxy)-2,4-dimethyl-5-tridecyn-3-ol
• 英文别名: (2S,3R,4R)-2,4-dimethyl-1-phenylmethoxytridec-5-yn-3-ol
• CAS: 157379-07-2
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: OXVYQXOPRDIDCQ-RZUBCFFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-(-)-1-(Benzyloxy)-2,4-dimethyl-5-tridecyn-3-ol 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(2S,4R)-(-)-1-(Benzyloxy)-2,4-dimethyl-5-tridecyn-3-one
  参考文献：
  名称：

  Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents

  摘要：

  The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3 . OEt(2) promotion), syn,anti (MgBr2 . OEt(2) promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.

  DOI：

  10.1021/jo00122a041
• 作为产物：
  描述：

  (2S)-3-(benzyloxy)-2-methylpropanal 、 三丁基(十一碳-2,3-二烯-4-基)锡烷 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2S,3R,4R)-(-)-1-(Benzyloxy)-2,4-dimethyl-5-tridecyn-3-ol
  参考文献：
  名称：

  Synthesis of Syn and Anti Homopropargylic and Allenic Alcohols through Diastereoselective SE2' Addition of a Common Chiral Allenylstannane Precursor to Aldehydes

  摘要：

  The (tri-n-butylallenyl)stannanes 3 and 17 afford the allenyl adducts 8 and 19 upon brief treatment with stannic chloride and then addition of isobutyraldehyde, whereas preequilibration with SnCl4 and subsequent aldehyde addition leads to the anti homopropargylic adducts 5 and 19.

  DOI：

  10.1021/jo00092a001

文献信息

• Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents
  作者：James A. Marshall、Jolyon F. Perkins、Mark A. Wolf

  DOI：10.1021/jo00122a041

  日期：1995.9

  The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3 . OEt(2) promotion), syn,anti (MgBr2 . OEt(2) promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.
• Synthesis of Syn and Anti Homopropargylic and Allenic Alcohols through Diastereoselective SE2' Addition of a Common Chiral Allenylstannane Precursor to Aldehydes
  作者：James A. Marshall、Jolyon Perkins

  DOI：10.1021/jo00092a001

  日期：1994.7

  The (tri-n-butylallenyl)stannanes 3 and 17 afford the allenyl adducts 8 and 19 upon brief treatment with stannic chloride and then addition of isobutyraldehyde, whereas preequilibration with SnCl4 and subsequent aldehyde addition leads to the anti homopropargylic adducts 5 and 19.